Crosslinking Dyeing Process of A Tetraethylene Pentamine Dye on ...

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The Proceedings <strong>of</strong> the 3rd International Conference on Functional Molecules Cl N Cl N N Cl + H 2 N SO 2 CH 2 CH 2 OSO 3 Na pH6~7 0~5 Cl N Cl N N NH SO 2 CH 2 CH 2 OSO 3 Na H 2 N SO 2 CH 2 CH 2 OSO 3 Na NaO 3 SOH 2 CH 2 CO 2 S NH N NH SO 2 CH 2 CH 2 OSO 3 Na 40 pH6~7 N N Cl Scheme 1 O C 8 N 5 H 22 O C 8 N 5 H 22 Scheme 2 (120 g/m 2 ) and degummed and bleached silk (90 g/m 2 ) were used throughout the study. 1,3,5- trichloro-2,4,6-triazine and p-(βsulphatoethylsulphony)aniline ester were industrial product without purification. A blue tetraethene pentamine dye (λmax = 602 nm in water) was prepared according to the method described by Murdock [4] . All other chemicals were analytical grade quality (Shenyang Chemical Reagent Factory, Liaoning China). FTIR spectra <strong>of</strong> DAST were measured with NEXUS FT-IR spectrophotometer (KBr). Mass spectrum <strong>of</strong> DAST was determined by a HP1100 system <strong>of</strong> HPLC/MS with atmospheric pressure chemical ionization (APCI) technique. 2.2 Synthesis <strong>of</strong> crosslinker To a suspension <strong>of</strong> 1,3,5-trichloro-2,4,6- triazine (19.4 g, 0.105 mol) in ice water was added a neutral solution <strong>of</strong> p-(βsulphatoethyl -sulphony)-aniline ester (30.3 g, 0.100 mol), and the mixture was stirred under cooling while controlling the pH to 7 or below with a 20% aqueous sodium carbonate solution. The end <strong>of</strong> the first condensation was determined by the Erich agent. When p-(β-sulphatoethyl-sulphony) –aniline ester disappeared, the temperature <strong>of</strong> resultant mixture was then raised to 40 , and aqueous p-(βsulphatoethyl-sulphony)–aniline ester (30.3 g, 0.100 mol) solution was added thereto. When there was no p-(βsulphatoethylsulphony)aniline ester, the second condensation was ended. Then the reaction mixture was salted out with a 20% aqueous sodium chloride solution. After removed salt, the product was yielded 90.7% (64.7 g). 2.3 <strong>Crosslinking</strong> dyeing process <strong><strong>Dye</strong>ing</strong> with the blue tetraethylene pentamine dye on cotton and silk was carried out by use <strong>of</strong> a “two-dip-two-nip” operation at room temperature. The fiber was dipped in the dye bath containing 3% (wt/wt) blue polyamine dye at a liquor-to-goods ratio <strong>of</strong> 20 : 1 for 3 min, and nipped with 70% wet pick-up. After the dyed fiber had been dried at the room temperature, it was dipped into the crosslinking bath for another 3 min and nipped once with approximately 70% wet pick-up. Then the fiber was heated in an oven for 10 min, and then soaped using 2 g/l anionic detergent (sodium dodecyl benzene sulphonate; 10 min, 60 ), washed and air dried. Finally, the soaped fiber was treated with DMF/water (1:1) at the boil. 2.4 Measurement <strong>of</strong> dye fixation The fixation <strong>of</strong> the blue polyamine dye was 307
TANG Yan-feng et al. <strong>Crosslinking</strong> <strong><strong>Dye</strong>ing</strong> <strong>Process</strong> <strong>of</strong> A <strong>Tetraethylene</strong> <strong>Pentamine</strong> <strong>Dye</strong> on Cotton and Silk calculated first by determining the reflectance (R) <strong>of</strong> the dyed samples at the wave length <strong>of</strong> maximum absorption on a Pye-Unicam SP8400 Spectrophotometer. The color yield (K/S) was calculated according to the Kubelka-Munk equation (Eqn 1). K/S values were measured twice: before soaping process [(K/S) b ] and after soaping treatment [(K/s) a ]. Percent fixation <strong>of</strong> the dye was calculated as follows (Eqn 2). K/S = (1R) 2 / 2R (1) <strong>Dye</strong> fixation (%) = [(K/s) a / (K/S) b ]×100 (2) 2.5 Fastness testing The colour fastness <strong>of</strong> the dyed fabrics was tested according to Chinese standard methods including fastness to light [GB8427-87], washing [GB/T 3921-97] and rubbing [GB/T 3920-97]. 3. Results and Discussion 3.1 Structure confirmation <strong>of</strong> DAST IR spectra <strong>of</strong> DAST exhibits the typical bands <strong>of</strong> ν C=N at 1550 cm -1 and at 1510 cm -1 in the s-triazine ring, the stretching bands <strong>of</strong> ν C=C for phenyl group at 1610, 1550 cm -1 , and the band <strong>of</strong> ν S=O for sulfonic group at 1241 cm -1 . MS (APCI) spectrum <strong>of</strong> DAST gives a correct series <strong>of</strong> quasimolecular ion peaks (M-Na) at m/z 693.9, and (M-2Na)/2 at m/z 335.5. So the structure <strong>of</strong> DAST was confirmed. 3.2 <strong>Dye</strong>-crosslinker-fiber bond The crosslinking dye was linked to the fiber by hydrogen bond and van der Waal’s forces before crosslinking dyeing process, these weak bonds are not strong enough to fix the dye to fiber, which was proved by Table 1, the fixation was only about 20% with zero crosslinker usage. Moreover the crosslinking dyed fiber was soaped with a mild detergent for 10 min (100 ) and subsequently treated with DMF without bleeding. Although this could not prove the covalent bond among them obviously, there was no dye washed <strong>of</strong>f after bleeding with DMF/water still indirectly gave the pro<strong>of</strong> <strong>of</strong> that the covalent bond formed between the tetraethylene pentamine crosslinking dye and fiber after crosslinking dyeing process. 3.3 Effect <strong>of</strong> concentrations <strong>of</strong> DAST on fixation The results obtained for the effect <strong>of</strong> the concentrations <strong>of</strong> crosslinkers on cotton and silk are shown in Table1. It demonstrate that the concentrations <strong>of</strong> crosslinkers have a great effect on the fixation <strong>of</strong> the dye. High stable fixations were obtained when the concentrations were more than 5% (wt/wt). At concentrations <strong>of</strong> less than 5% (wt/wt), the amount <strong>of</strong> crosslinker molecules were not enough to complete the crosslinking reaction between the dye and the fiber, therefore the fixation was lower than 99%. At concentrations over 5% (wt/wt), the amount <strong>of</strong> crosslinker molecules is enough to fully complete the crosslinking reaction, so the high stable fixation was obtained. Table 1 Effect <strong>of</strong> concentrations <strong>of</strong> DAST on fixation Conc. Of DAST (wt/wt%) 0 1 3 5 7 Fixation (%) Cotton Silk 20.1 15.9 84.6 87.3 98.4 98.9 99.2 99.3 99.3 99.5 <strong>Crosslinking</strong> bath pH=8.0, the fabric was cured at 60 for 10min. 3.4 Effect <strong>of</strong> cured temperature on fixation The results <strong>of</strong> the dye fixation with varying cured temperature using DAST are shown in Figure 1. This figure shows that the plot reached a plateau over a fixation value <strong>of</strong> 99% when the cured temperature reached 60. This might be attributed to the reactivity <strong>of</strong> the crosslinker, because the reaction temperature <strong>of</strong> the βsulphatoethyl-sulphony group is about 60. At lower temperature, the crosslinker might react with the amino group in the dye, but could not react with the hydroxyl group in the fiber, which 308
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