Study On Vinylsulfone Reactive Dyes Containing Benzsulfamide Moiety

Reactive dyes are important dyes for cellulose fiber dyeing,especially the vinylsulfone reactive dyes occupy a huge share in the dye market.Black reactive dyes are those with the most extensive use and the most production of reactive dyes,especially C.I.Reactive Black 5.Almost all the navy blue components of reactive black dye goods used Reactive Black 5 as the main ingredient.Reactive Turquoise Blue is also a hot dye in recent years with bright color and low cost,and it is commonly used in the cotton knitted fabrics dyeing.In order to improve the dye uptake rate and fixation rate of C.I.Reactive Black 5 and C.I Reactive Turquoise Blue 21,several novel reactive dyes were designed and synthesized from a new reactive dye intermediate containing benzsulfamide moiety and other dyestuff precursors.The dissertation mainly contains the following aspects:1.Synthesis of the reactive dye intermediate compound 4 containing benzsulfamide moiety.In this experiment,the final reaction process in the synthesis of intermediate compound 4 was improved.In the presence of 98% sulfuric acid,the hydrolysis and esterification reactions were conducted in one pot by heating for 9 hours to obtain compound 4 in 65% yield.The amino value and the esterification value of the synthesized intermediate were determined to be 94.6% and94.3%,respectively.2.Synthesis of dye compounds D1-D6.For the reactive black dyes,the synthetic route was optimized on the basis of the traditional synthetic method of C.I.Reactive Black 5.The diazonium salt from the new intermediate was prepared and used to couple with H-acid for synthesis of three new black reactive dyes D2-D4.For the reactive turquoise dye,the new blue reactive dye D6 was obtained by replacing the p-ester in the condensation reaction with compound 4 on the basis of the synthetic method of Reactive Turquoise Blue 21.The structures of the synthesized novel dyes were characterized by ¹H NMR,¹³C NMR,MS and IR spectra.3.Dyeing properties of several synthesized dyes.Application of the synthesized dyes on cotton fabric was studied and the effects of dye uptake rate and fixation rate with the change ofdyeing time and salt concentration were studied.The results showed that dye D1-D4 had the similar curve of the dye uptake and fixation rate and the dye uptake and fixation rate of dye D4 was the highest among these reactive dyes.When the salt concentration was increased to 30 g/L,the rate of dye D4 uptake and fixation changed little,the salt-resistant stability of dye D4 was good.At the same time,the fastness test on the synthesized dyes revealed that the fastness of six vinylsulfone reactive dyes on the cotton fiber met the application requirements.Dye D4 showed excellent light fastness with grade 5 and color fastness of the dyes were all good.Moreover,part of the fixation rate reached 78%.Therefore these new dyes can be used for high fixation rate dyeing.