Three novel azocalix [4] arene compounds were synthesized through diazo-coupling reaction using calix [4] arene, benzocaine, tricaine and procaine hydrochloride as raw materials, and the yield of com⁃pounds 6a, 6b and 6c was up to 83%, 81% and 83%, respectively. The compound structure was character⁃ized by IR, 1H NMR and elemental analysis. The spectra properties of azocalix [4] arene in different pH of solu⁃tion were investigated by UV-Vis. The dyeing properties were studied by the dyeing curve, color depth and fastness test. The results indicated that the increase of pH led to azo-quinoid tautomerizm phenomena of azo⁃calix [4] arene compounds 6a, 6b and 6c, and the maximum absorption peak occurred red-shift. The novel azo⁃calix [4] arene compounds had an outstanding dyeing ability under basic condition than acid condition, and the dyeing percentage of compound 6a was as high as 78%, the K/S value was 2.798, the soaping fastness and dry and wet rubbing fastnesses were al level 4, indicating the compound 6a was a good disperse dye.%以杯[4]芳烃、苯佐卡因、三卡因和盐酸普鲁卡因为原料，通过芳胺的重氮化－偶合反应合成了3个新型的偶氮基杯[4]芳烃衍生物6a、6b、6c，收率分别为83%、81%、83%。经IR、1H NMR和元素分析进行结构表征。通过紫外可见光谱考察了偶氮基杯[4]芳烃衍生物在溶液不同pH条件下的光谱性质，并通过上染曲线、得色深度、色牢度研究其染色性能。结果表明，随着pH的增大，偶氮基杯[4]芳烃衍生物6a、6b、6c发生偶氮-醌腙异构互变，最大吸收峰红移；化合物在碱性条件下的染色效果比酸性条件好，其中化合物6a的上染率高达78%，表面得色深度为2.798，耐干、湿摩擦色牢度和耐皂洗色牢度均为4级，是一种较好的分散染料。
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