Abstract Nitrocellulose (NC)-based propellants require stabilizers to avoid early decomposition or even explosion during storage. A series of novel fullerene-malonamide derivatives with different carbon chain lengths on the p-position of the benzene ring was synthesized as stabilizers for NC-based propellants through the Bingel reaction because of the excellent thermal stability and strong ability of these derivatives to eliminate free radicals. The molecular structures of these fullerene-malonamide derivatives were verified via 1H nuclear magnetic resonance (NMR) spectroscopy, 13C NMR spectroscopy, Fourier-transform infrared (FT-IR) spectroscopy, ultraviolet–visible spectroscopy, and high-resolution mass spectrometry. Meanwhile, their stability was investigated using methyl violet, vacuum stability, and weight loss tests. Results indicated that the stability of the novel fullerene-malonamide derivatives was considerably better than that of traditional stabilizers, such as N,N′-dimethyl-N,N′-diphenylurea and diphenylamine. Moreover, these derivatives exhibited excellent thermal stability at high temperatures. The stability of the fullerene-malonamide derivatives also improved as the carbon chain length on the p-position of the benzene ring on C60 increased. In addition, the stability mechanism of the fullerene-malonamide derivatives was studied through electron paramagnetic resonance spectroscopy, FT-IR spectroscopy, and liquid chromatography-mass spectrometry. Results turned out that the fullerene-malonamide derivatives could react with nitroxide radicals released from the pyrolysis of NC. Hence, these novel fullerene-malonamide derivatives can be used as promising stabilizers for NC-based propellants.

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硝基推进剂中富勒烯-丙二酰胺衍生物新型稳定剂的合成及稳定机理

摘要 硝化纤维素 (NC) 基推进剂需要稳定剂，以避免在储存过程中过早分解甚至爆炸。苯环对位具有不同碳链长度的一系列新型富勒烯-丙二酰胺衍生物由于具有优异的热稳定性和较强的消除游离态的能力，通过Bingel反应合成了一系列作为NC基推进剂的稳定剂。自由基。这些富勒烯-丙二酰胺衍生物的分子结构通过 1 H 核磁共振 (NMR) 光谱、13 C NMR 光谱、傅里叶变换红外 (FT-IR) 光谱、紫外-可见光谱和高分辨率质谱进行了验证。同时，使用甲基紫、真空稳定性和失重试验研究了它们的稳定性。结果表明，新型富勒烯-丙二酰胺衍生物的稳定性明显优于传统稳定剂，如N,N'-二甲基-N,N'-二苯脲和二苯胺。此外，这些衍生物在高温下表现出优异的热稳定性。富勒烯-丙二酰胺衍生物的稳定性也随着 C60 上苯环对位碳链长度的增加而提高。此外，通过电子顺磁共振光谱、FT-IR光谱和液相色谱-质谱法研究了富勒烯-丙二酰胺衍生物的稳定性机制。结果表明，富勒烯-丙二酰胺衍生物可以与NC热解释放的氮氧自由基反应。因此，