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Synthesis of Novel Reactive Dyes for Textile Applications CHEMISTRY

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Synthesis of Novel Reactive Dyes for Textile Applications CHEMISTRY Synthesis of Novel Reactive Dyes for Textile Applications By Umme Habibah Siddiqua (M.Phil UAF) 2009-ag-107 A Thesis Submitted in Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILISOPHY IN CHEMISTRY DEPARTMENT OF CHEMISTRY AND BIOCHEMISTRY FACULTY OF SCIENCES UNIVERSITY OF AGRICULTURE FAISALABAD 2016 i ii iii My Affectionate Parents Whose esteemed love enabled me to get the success and whose hearts are always beating to wish for me maximum felicity in life. iv v ACKNOWLEDGEMENT All praises to Almighty ALLAH, the creator, dominant, self existing and sustainer, who enabled me to accomplish this project and all respect is for his last Prophet MUHAMMAD (Peace and Blessing of Allah Be Upon Him) who is forever a torch of guidance and knowledge in our life. I pay my humble gratitude to my worthy supervisor Dr. Shaukat Ali, Dept. of Chemistry, University of Agriculture, Fasisalabad and Co-Supervisor Dr. Tanveer Hussain, Dept. of Textile Processing, National Textile University, Faisalabad for their absorbing attitude, constant guidance, timely suggestions, inspiration and encouragement throughout my studies. I offer my cordial and profound thanks to Prof. Dr. Haq Nawaz Bhatti Chairman, Dept. of Chemistry, University of Agriculture, Fasisalabad and Prof. Dr. Asgher Bajwa for their co-operation, valuable suggestions and guidance during my research and compilation of my thesis. I am lucky enough to have the support of many good friends. Special thanks are extended to Asma Hanif, Anum Sahar, Asma Tufail, Sana Sadaf, Sana Nosheen, Shazia Muzzafar for their prayers, moral support and sincere suggestions. I want to express my gratitude, deep appreciation and very special thanks to Textile processing staff of the National Textile University, Faisalabad, without their help, moral support and encouragement it would not be possible for me to complete my degree in such a good way. Special thanks are due to my all lab fellows for their friendly behaviour and co- operation during research work. Words always seem to shallow whenever it comes to my dearest and loving parents. I am absolutely nothing without their encouragement and especially their prayers. My appreciation and great thanks are extended to my brothers especially to Habib-ur- Rehman, sisters and all other family members who prayed for me. Last but not the least thanks are extended to Higher Education Commission of Pakistan for their financial support during this project. UMME HABIBAH SIDDIQUA vi LIST OF TABLES Sr. No TITLE PAGE NO. 3.1 (a) List of chemicals used for research work 26 3.1(b) List of chemicals used for research work 27 3.2 Specifications of the 100% cotton fabric used in this study 28 3.3(a) List of equipments used for characterization and application of 39 dyes 3.3(b) List of equipments used for characterization and applications of 30 dyes 3.4 Optimization of dyeing quality parameters using RSM (Response 47 surface Methodology) 3.5 Optimization of dyeing parameters for pad- thermosol dyeing 48 method 3.6 Protection categories of fabrics according to ASTM D6603 52 3.7 54 Optimization of process parameters for maximum dye removal through Advanced Oxidation Processes 4.1 UV/Vis. Spectra (λmax) of aqueous solutions of novel reactive 55 dyes 4.2 Stretching and bending frequencies of characteristics functional 61 groups present in dye D-1 4.3 Stretching and bending frequencies of characteristics functional 62 groups present in dye D-2 4.4 Stretching and bending frequencies of characteristics functional 63 groups present in dye D-3 4.5 Stretching and bending frequencies of characteristics functional 64 groups present in dye D-4 4.6 Stretching and bending frequencies of characteristics functional 65 groups present in dye D-5 4.7 Stretching and bending frequencies of characteristics functional 66 groups present in dye D-6 4.8 ANOVA results for the exhaustion of D-1 through RSM 76 vii 4.9 ANOVA results for the exhaustion of D-2 through RSM 76 4.10 ANOVA results for the exhaustion of D-3 through RSM 77 4.11 ANOVA results for the exhaustion of D-4 through RSM 77 4.12 ANOVA results for the exhaustion of D-5 through RSM 78 4.13 ANOVA results for the exhaustion of D-6 through RSM 78 4.14 Analysis of variance (ANOVA) results for (Exhaustion) response 80 parameters 4.15 ANOVA results for the fixation of D-1 reactive dye through 90 RSM 4.16 ANOVA results for the fixation of D-2 reactive dye through 91 RSM 4.17 ANOVA results for the fixation of D-3 reactive dye through 91 RSM 4.18 ANOVA results for the fixation of D-4 reactive dye through 92 RSM 4.19 ANOVA results for the fixation of D-5 reactive dye through 92 RSM 4.20 ANOVA results for the fixation of D-6 reactive dye through RSM 93 4.21 Analysis of variance (ANOVA) results for (fixation) response 94 parameters 4.22 Optimum dyeing conditions for the maximum exhaustion and 110 fixation of the novel dyes 4.23 Colorimetric data of the synthesized dyes by exhaust dyeing 113 4.24 Colorimetric data of the synthesized dyes by pad dyeing 114 4.25 Fastness properties of the novel dyes on the dyed cotton fabric 118 by exhaust dyeing 4.26 Fastness properties of the novel dyes on the dyed cotton fabric 118 by pad thermosol dyeing 4.27 Fastness properties of the novel dyes on the dyed cotton fabric 119 by printing 4.28 Ultraviolet Protection Factor of the fabric dyed by novel azo 120 reactive dyes 4.29 UV/Vis. Spectra (λmax) of aqueous solutions of degraded novel 130 reactive dyes viii LIST OF FIGURES Sr. TITLE PAGE No NO. 1.1 General features of a typical reactive dye 2 1.2 Reactions involving a triazinyl halide type reactive dye 3 1.3 Reactions involving a VS reactive dye 4 3.1 General Synthesis Scheme for Novel Dyes D-1 and D-2 31 3.2 Chemical structure of azo reactive dye D-1 35 3.3 Chemical structure of azo reactive dye D-2 35 3.4 General Synthesis Scheme for Novel Dyes D-3, D-4, D-5 and D-6 36 3.5 Chemical structure of azo reactive dye D-3 40 3.6 Chemical structure of azo reactive dye D-4 40 3.7 Chemical structure of azo reactive dye D-5 41 3.8 Chemical structure of azo reactive dye D-6 41 3.9 Flow sheet diagrams for purification of synthesized dyes 42 4.1 UV-Vis spectra of reactive azo dye D-1 56 4.2 UV-Vis spectra of reactive azo dye D-2 56 4.3 UV-Vis spectra of reactive azo dye D-3 57 4.4 UV-Vis spectra of reactive azo dye D-4 57 4.5 UV-Vis spectra of reactive azo dye D-5 58 4.6 UV-Vis spectra of reactive azo dye D-6 58 4.7 FTIR spectrum of novel reactive dye D-1. 61 4.8 FTIR spectrum of novel reactive dye D-2 62 4.9 FTIR spectrum of novel reactive dye D-3 63 4.10 FTIR spectrum of novel reactive dye D-4 64 4.11 FTIR spectrum of novel reactive dye D-5 65 4.12 FTIR spectrum of novel reactive dye D-6 66 4.13 ESI-MS spectrum of the Dye D-1 68 4.14 ESI-MS spectrum of the Dye D-2 68 4.15 ESI-MS spectrum of the Dye D-3 69 4.16 ESI-MS spectrum of the Dye D-4 69 ix 4.17 ESI-MS spectrum of the Dye D-5 70 4.18 ESI-MS spectrum of the Dye D-6 70 4.19 Effect of dyeing temperature on color strength percentage of novel dyes by 72 pad thermosol method on cotton fabric 4.20 Effect of dyeing time on color strength percentage of novel dyes by pad 73 thermosol method on cotton fabric 4.21 Effect of dyeing pH on color strength percentage of novel dyes by pad 74 thermosol method on cotton fabric 4.22 The normal plot of residuals for exhaustion response of reactive dyes (A) 81 D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5(F) D-6 4.23 The actual and predicted values of exhaustion response for reactive dyes 82 (A) D-1 (B) D-2(C) D-3 (D) D-4 (E) D-5 (F) D-6 4.24 Overlay Perturbation plot of all the independent variables for exhaustion of 84 dye (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5(F) D-6 4.25 Response surface plots showing interaction of temperature and salt on 86 exhaustion of dye (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.26 Response surface plots showing interaction of temperature and alkali on 88 exhaustion of dye (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E)D-5(F) D-6 4.27 Response surface plots showing interaction of salt and alkali on exhaustion 89 of dye (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.28 The normal plot of residuals for fixation response of reactive dyes (A) D-1 95 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.29 The actual and predicted values of fixation response for reactive dyes (A) 96 D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.30 Overlay Perturbation plot of all the independent variables for fixation of 98 reactive dyes (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E)D-5 (F)D-6 4.31 Response surface plots showing interaction of temperature and salt on 100 fixation of reactive dyes (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.32 Response surface plots showing interaction of temperature and alkali on 102 fixation of reactive dyes (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.33 Response surface plots showing interaction of salt and alkali on fixation of 103 reactive dyes (A) D-1 (B) D-2 (C) D-3 (D) D-4 (E) D-5 (F) D-6 4.34 Diagram showing the principles of ionic assembly followed by covalent 105 x fixation at elevated temperatures 4.35 Representation of a diffuse electrical double layer consisting of a 106 negatively charged substrate in water 4.36 Mechanistic pathway of cotton fiber reaction with synthesized reactive 109 dyes 4.37 Color strength percentage of cotton printed fabric before and after washing 111 4.38 Tautomerism in reactive dyes 116 4.39 Effect of pH on the decolorization efficiency of six novel reactive by 122 Fenton oxidation.
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