Syntheses And Characterizations Of Anthraquinonoiddisperse Reactive Dyes Applicable In SCF-CO₂

The coloration technology in supercritical carbon dioxide?SCF-CO₂?with water free is a new methodology for textiles.Due to its advantages of no consumption of water and no discharging of effluent,it facilitates the transformation and upgrading of printing and dyeing industry.So far,the colorations of synthetic fibres in supercritical carbon dioxide have been achieved successfully,yet there are still some problems on the colorations of natural fibres.Fortunately,the utilization of disperse reactive dyes can solve these problems to a certain extent.The objective of this work is to develop and synthesize some novel anthraquinonoid disperse reactive dyes which could be applicable in supercritical carbon dioxide medium.First of all,based on the copper-catalyzed Ullmann reaction,the factors of the reaction between 1-chloroanthraquinone and N-phenylethylenediamine were investigated,such as the solvent,base,copper-containing catalyst,volume of the solvent,molar ratio of the reactants,amount of potassium hydroxide?KOH?and copper,reaction temperature and time.The results demonstrate that the solvents of N,N-dimethylformamide?DMF?,dimethyl sulfoxide?DMSO?and toluene,the bases of KOH,trimethylamine?Et₃N?and potassium carbonate?K₂CO₃?,especially the base of KOH,were suitable for this reaction system.The copper-containing catalyst had little effect on Ullmann reaction,except the catalyst with an anion of I^-,which could decrease the yield of the target product.Furthermore,the effects of volume of the solvent,reaction temperature and time on this cross-coupling reaction were greater than the remaining three factors.Afterwards,the precursors with different structures were obtained by the cross-coupling reaction between 1-chloroanthraquinone and different amines,and three dichlorotriazine dyes?or two?-bromoacrylamide dyes?were synthesized successfully via a nucleophilic substitution reaction by utilization of the dye precursors and cyanuric chloride?or 2,3-dibromopropionyl?.Addtionally,the five anthraquinonoid disperse reactive dyes were characterized from chemical structures by Fourier transform infrared?FT-IR?spectra,nuclear magnetic resonance spectroscopy(¹H and ¹³C NMR),elemental analysis?EA?and liquid chromatography-mass spectrometry?LC-MS?.Besides,the results of Uv-vis absorption spectra claim that hypsochromic shift was observed by introduction of dichlorotriazine or?-bromoacrylamide reactive group.And the three dichlorotriazine dyes were in red hue while the other two?-bromoacrylamide dyes were in purplish red hue.Meanwhile,solvatochromism was viewed for all the obtained dyes,and these anthraquinonoid disperse reactive dyes were sensitive to base rather than acid.Finally,one dichlorotriazine dye and one?-bromoacrylamide dye were applied to the colorations of natural fibres?cotton,silk and wool?in supercritical carbon dioxide,and their dyeing properties were preliminary discussed.The results imply that red colors with different chromatic lights were achieved for the samples,and better coloration properties with excellent washing and rubbing fastness of the obtained dyes were observed on silk and wool than cotton substrate.