油溶性1,8-萘酰亚胺类荧光化合物的合成与应用

以4-溴-1,8-萘酐为原料经过亚胺化和取代反应合成4-烷氧基-N-十八烷基-1,8-萘酰亚胺类荧光化合物。并以产率为指标讨论了影响亚胺化反应的因素, 得到优化的亚胺化工艺条件, 即反应温度50 ℃, 反应时间3 h, 4-溴-1,8-萘酐与十八胺的物质的量比为1∶1.08, 所得中间产物4-溴-N-十八烷基-1,8-萘酰亚胺的产率可达81.6%。中间产物的红外光谱表明生成的产物符合要求。对目标产物4-烷氧基-N-十八烷基-1,8-萘酰亚胺进行了荧光光谱测定, 在464 nm波长激发下样品的荧光光谱表明, 该类化合物在510～550 nm之间有明显的发射峰。目标产物在空调系统润滑油中有较好的溶解性, 在紫外灯照射下有较强的绿色或黄绿色荧光。

Synthesis and Application of Oil-Soluble Fluorescent Dyes Based on 1,8-Naphthalimide

4-bromine-1,8-naphthalic anhydride as raw material through the imidization and substitution reaction can get 4-alkoxy-N-18 alkyl-1,8-naphthalimide fluorescent compounds. The yield is as indicators to discuss the factors impacting on the imidization and the imidization process was optimized further. The reaction temperature was 50 ℃. The reaction time was 3 h. The molar ratio of 4-bromine-1,8-naphthalene anhydride and 18 amines was 1∶1.08. The yield of 4-bromine-N-18 alkyl-1,8-naphthalimide is up to 81.6%. The infrared spectra of the intermediate product showed it agreed with the requirement. The fluorescence spectra of the target products 4-alkoxy-N-18 alkyl-1,8-naphthalimide was detected. The fluorescence spectra showed that these compounds had obvious emission peak in the range of 510～550 nm wavelength when the excitation wavelength was 464 nm. Target products in the lubricants of automotive air-conditioning systems have better solubility, and they give notable green or yellow-green fluorescent in ultraviolet light exposure.