Syethesis Of Water-soluble Fluorescent Dyes And Its Application In The Functionalization Of Acid Yellow Dyes

As a functional dye,fluorescent dyes have been widely used in our daily production,such as fluorescent whitening agents,fluorescent printing pigments and textiles,in addition to fluorescent inks,fluorescent chemical analysis,organic light guide materials,dye lasers,Fluorescent paints,military fluorescent sources,liquid crystal displays,biomedical fluorescent tracers and large equipment inspections also have important positions.The fluorescent dyes we use now are simply divided into the following categories according to their chemical structures:such as coumarins,1,8-naphthalimide,benzanthrones,anthraquinones,rhodamines.However,most of the fluorescent dyes we are currently studying are relatively poor in water solubility,and generally can only be used in the coloring of plastics and synthetic fibers.Fluorescent dyes for dyeing wool and silk need to have good water solubility and water solubility.Better fluorescent dyes can also be used in the fields of medicine,biology and agriculture.The solubility of fluorescent dyes limits their application to a certain extent,so improving the water solubility of fluorescent dyes has important practical application prospects.1,8-Naphthalimide compounds are a very important class of functional dye intermediates,and also the parent luminous chromophore of a class of fluorescent dyes.This type of fluorescent dyes have strong fluorescence,easy structure modification,bright color,good Stability and photophysics.Therefore,in this paper,1,8-naphthalenedicarboxylic anhydride,which is non-toxic,cheap,easy to modify and has good stability,is selected as the parent structure.By introducing water-soluble groups on the matrix to enhance the water solubility of these compounds,three kinds of 1,8-naphthalimide water-soluble fluorescent dyes were designed and synthesized,and their structural characterization and optical performance tests were carried out.Choose two kinds of dyes with better fluorescence performance to mix with the specified acid yellow dye to explore the fluorescence performance and dyeing performance of dyed cotton fabric.The work divided into the following three parts:Part 1:Using 1,8-naphthalene dicarboxylic anhydride as the parent material,six kinds of1,8-naphthalimide compounds,A₁ to A₆,were synthesized by reacting with water-soluble small molecule compounds,and the yields were 82.4%,92.0%,85.7%,77.7%,65.2%,87.3%.Part 2:Testing of optical properties of compounds.Three of the six compounds synthesized were screened for fluorescence performance testing.Explore the fluorescence intensity and relative fluorescence quantum yield of fluorescent compounds in different concentration ranges of different solvents,such as DMF,water,methanol,acetone,ethanol,acetonitrile,and determine the optimal solvent and optimal concentration of the fluorescent compound.Compound A₁ has the strongest fluorescence intensity in ethanol.When the concentration is 1.0×10^–5 mol/L,the fluorescence intensity reaches a maximum of 1.68×10⁷;the maximum fluorescence quantum yield when using water as a solvent is 50.1%At this time,the concentration is 0.6×10^–5 mol/L.Compound A₃ has the strongest fluorescence intensity in water.When the concentration is 0.4×10^–4 mol/L,the fluorescence intensity reaches the maximum value of 0.6×10⁸;the fluorescence quantum yield when water is used as the solvent is also 30.6%At this time,the concentration is0.8×10^–4 mol/L.Compound A₆ has the strongest fluorescence intensity in water.When the concentration is 0.4×10^–4 mol/L,the fluorescence intensity reaches the maximum value of 0.55×10⁸;the fluorescence quantum yield when water is used as the solvent is also 31.6%At this time,the concentration is 0.4×10^–4 mol/L.Part 3:Use two kinds of fluorescent dyes and the specified acid yellow dye as raw materials to carry out the compounding and blending of the dyes,and use the compounded dyes for dyeing cotton fabrics,by dyeing the K/S value of the cotton fabrics,R value,dyeing fastness,fluorescence intensity to explore the best dyeing process conditions,and explore the influence of dyeing temperature,bath ratio,time and dye concentration on the dyeing performance and fluorescence performance of dyed cotton fabrics.The comparison of experimental results found that when the concentration of the fluorescent dye A₁ was 6%,the concentration of the acid yellow dye was 2%,the dyeing time was 30 min,the dyeing temperature was 70°C,and the bath ratio was 1:25,the fluorescence effect of the dyed fabric was the best,and the fluorescence intensity was 1.87×10⁷;the concentration of fluorescent dye A₁ is 2%,the concentration of acid yellow dye is 2%,the dyeing time is 10 min,the dyeing temperature is 80?,the dyeing effect of the dyed fabric is best when the bath ratio is 1:40,K/S value The maximum is 1.56.When the concentration of the fluorescent dye A₃ is 5%,the concentration of the acid yellow dye is 2%,the dyeing time is 50 min,the dyeing temperature is 98°C,and the bath ratio is 1:20,the fluorescence effect of the dyed fabric is the best,and the fluorescence intensity is 2.90×10⁷;the concentration of fluorescent dye A₃ is 1%,the concentration of acid yellow dye is 2%,the dyeing time is 40 min,the dyeing temperature is 98?,the dyeing effect of the fabric is the best when the bath ratio is1:35,and the maximum K/S value is 1.14.