Research on Synthesis of New Azo Calix[4]arene and its Dyeing Properties

¹ School of Chemical Engineering and Technology, Wuhan University of Science and Technology, Wuhan, Hubei, China
² Department of Chemical & Pharmacy Engineering of Huaxia College, Wuhan University of Technology, Wuhan, Hubei, China
³ School of Chemical Engineering and Technology, Wuhan University of Science and Technology, Wuhan, Hubei, China

^* Corresponding author: lzs1961@yahoo.com.cn

Abstract

With the raw materials of calix[4]arene, benzocaine, tricaine and procaine hydrochloride, three new azo calix[4]arene derivatives—6a, 6b and 6c are synthesized by diazotization–coupling reaction of an aromatic amine, with its yield of 83%, 81% and 83% respectively. The structural characterization is in a way of IR, ¹H NMR and elemental analysis. This paper investigates the spectral properties of azo calix[4]arene derivatives under different solution pH conditions through the UV–visible spectroscopy, and researches the dyeing properties through the dyeing curve, color yield test and fastness test. The results show that, with the increase of pH value, the azo calix[4]arene derivatives—6a, 6b and 6c form azo–hydrazone tautomeric isomers with the maximum absorption peak redshift; the dyeing effect of the compound is good, of which the dye–uptake rate of the compound 6a is as high as 78%; the surface depth of color yield is 2.798, and the dry and wet rubbing fastness and the soaping fastness are respectively 4, which is a better disperse dye.