一系列氯/間-羧基吡啶三嗪反應性染料合成和動力學研究及其棉纖維冷軋堆染色應用

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姓名

黃惠卿(Huei-Chin Huang) 查詢紙本館藏

畢業系所

化學學系

論文名稱

一系列氯/間-羧基吡啶三嗪反應性染料合成和動力學研究及其棉纖維冷軋堆染色應用
(Synthesis and kinetic study of a series of chloro/m–carboxypyridium triazinyl reactive dyes and their cold pad-batch cotton dyeing application)

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摘要(中)

本論文研究分為兩部分，第一部分為製備5支一氯–s–三嗪反應性染料(mono–chlororizainyl reactive dyes, MCT dyes)和5支間羧基吡啶–三嗪反應性染料(m–carboxypyridium triazinyl reactive dyes, NTR dyes)，並進行其水解動力學研究及冷軋捲堆(Cold pad‒batch, CPB)染色應用。此10支染料使用相同紅色色母，藉由改變三嗪環(triazinyl)碳上氮及氧取代基團來改變其反應性，染料結構則使用HPLC、FT-IR、NMR、LC-MASS和E.A.等儀器鑑定。5支NTR紅色染料的水解反應性均比其對應的MCT母體染料高；數據顯示不管是MCT紅色染料、或者是NTR紅色染料的水解常數 (kobs)，由高至低的排序均為甲氧基(OCH3) > N–甲基甲基磺酰氨基(N(CH3)SO2CH3) > N–甲基苯胺(N(CH3)phenyl) > 氰氨基(NHCN) > 羥基(-OH)的三嗪環“第二支腳”取代基染料，此趨勢與三嗪環“第二支腳”取代基在鹼性水溶液條件下的電子效應相關，因為-NHCN及-OH取代基上的proton，在pH為10.5的水溶液中解離而帶負電，分別形成-(NCN) ‒及-O‒，帶來較強的推電子效應，使三嗪環電子密度增加而降低反應基的活性，而-OCH3及-N(CH3)SO2CH3取代基屬於強拉電子基團，使得三嗪環反應基活性增加，而N–甲基苯胺(N(CH3)phenyl)取代基則屬於中等的推電子基團，因此反應基的反應性介於中間，此推論也使用Hammett substituent constants( meta)及電腦分子模擬數據來證實。
在CPB的棉纖維染色應用發現，10支紅色染料達到各自最佳染色力度值所需的軋染捲置時間，與該染料kobs數值呈反比，且當MCT染料被Nicotinic acid(Nic)取代後形成的NTR染料，在固著率及染深性有提升，當中以Red 1A(Cl/NHCN)及Red 1B(Nicotinic acid/ NHCN)取代基的染料，染色表現是同類型染料中最優異的。原因是Red 1A及Red 1B的氨腈基團(–CN)屬拉電子基團，在高pH值的CPB染色條件下，NHCN上的proton被部分解離而帶負電荷，此現象一方面能降低三嗪環上反應基的活性(kobs)，不容易被鹼性染液中的OH –取代而水解外，-(NCN) ‒帶負電荷且分子結構小，在低水浴、鹼性環境下的CPB染浴下，這類染料預期有較好的溶解度及較高的移動性，使氨腈基團(NHCN) 取代的Red 1A及Red 1B染料在冷軋堆染色(CPB)表現比其他紅色染料好。
第二部的研究是將前述10支紅色染料中染深性及固著率較優異的Nicotinic acid/ NHCN反應基組合導入藍色及橘色染料結構中，探究不同色母對kobs數值及CPB染色應用的影響。結果顯示不同色母的染料結構，對Nicotinic acid/ NHCN反應基的水解常數kobs數值影響不大，但是當與相同色母的傳統型雙反應基(Cl/SES)染料進行冷軋堆的染深性(Build up)比較，Nicotinic acid/ NHCN反應基組合應用於結構較小的色母，例如紅色及橘色染料，能明顯幫助染料在CPB染色力度的提升性，但是若應用在較大色母的藍色染料結構時，則還是以傳統型雙反應基(Cl/SES)藍色染料的染深性較高，此結果再次驗證了CPB染色的染深性，不能單純考慮反應基的kobs數值，還需要考慮染料的分子大小，以及染料在鹼性冷軋堆(Cold pad‒batch)溶液之溶解度等綜合效應。

摘要(英)

The content of this thesis is divided into two parts. The first part is the preparation of 5 monochloro–s–triazinyl reactive dyes (MCT dyes) and 5 m–carboxypyridium triazinyl reactive dyes (NTR dyes) which have with the same red chromophore only the substituent groups in trizaine ring are different. The hydrolysis kinetics and cold pad‒batch (CPB) dyeing application of these 10 red reactive dyes were explored and evaluated. The structure of all dyes were characterized by HPLC, FT-IR, NMR, LC-MASS and elemental analysis. The hydrolysis reactivity of the five NTR dyes are all higher than that of the parent MCT dyes. The hydrolysis constant (kobs) of MCT dyes and NTR dyes, from high to low, shows the same order as methoxy (OCH3) > N–methylmethyl sulfonyl (N(CH3)SO2CH3) > N(CH3)phenyl > cyanoamino(NHCN) > hydroxyl (OH) (which are the "second leg" substituents of the triazine dye). The order in hydrolysis reactivity is due to that the proton on -NHCN and -OH substituents is ionized to become negatively charged in the aqueous solution with pH equal to 10.5. The electronic donating effect of -(NCN) ‒ and -O‒ increases the electron density of the triazine ring and reduces the reactivity of the reactive group. The -OCH3 and -N(CH3)SO2CH3 substituents are stronger electron withdrawing groups, which increase the reactivity of the reactive group. While the N(CH3)phenyl substituent is a moderate electron donating group, so the reactivity is higher than -NHCN and -OH substituents but lower compared to -OCH3 and –N(CH3)SO2CH3 substituents. The Hammett substituent constants ( meta) and computational simulation data all support this conclusion.
In the CPB dyeing application, it was found that the optimal batch time to reach the highest dyeing strength (K/S) is negatively correlated with the kobs value of both MCT dyes and NTR dyes. The replacement of chloro by nicotinic acid from MCT dyes to NTR dyes can improve the dye fixation and build up property in CPB dyeing. Red 1A(Cl/NHCN) and Red 1B(Nicotinic acid/NHCN) dyes showed better dyeing performance comparing with the same type of other red dyes, presumably because of the cyanamide group (-NHCN) of Red 1A and Red 1B is an electron withdrawing group. Under high pH condition in CPB dyeing, the proton on -NHCN was partially dissociated. The negatively charged -(NCN)- stabilizes the reactive group in triazinyl ring and slows down the hydrolysis reaction by hydroxide (OH-) in strong alkali dyeing aqueous solution. In addition, the molecular size of NHCN substituent was smaller with negative charge, therefore has better solubility and mobility in an alkali low liquor dyeing bath compared to the other red dyes. These could be the reasons that Red 1A and Red 1B exhibit the best dyeing performance amongst the studied red dyes.
The second part of this thesis is to introduce the Nic/NHCN couple which displayed one of the best dyeing performance into a blue and a orange chromophore. It was found that different chromophore has little effect on the hydrolysis constant (kobs) but the build up performance of Red and Orange dyes with Nic/NHCN reactive group is better than the conventional Cl/SES reactive dyes with the same chromophores in CPB application while the Nic/NHCN reactive group in big Blue chromophore is not as good as the conventional Cl/SES reactive dye. This results confirm once again that the performance of CPB dyeing could not be only considered the kobs value of reactive group, the combination effects such as molecular size and the solubility of dye in alkali CPB condition should be taken into consideration.

關鍵字(中)

★ 氯/間-羧基吡啶
★ 三嗪反應性染料
★ 冷軋堆
★ 棉

關鍵字(英)

★ chloro/m–carboxypyridium
★ triazinyl reactive dyes
★ cold pad-batch
★ cotton

論文目次

目錄頁次
中文摘要 ------------------------------------------------------------------------ I
英文摘要 ------------------------------------------------------------------------ III
誌謝 ------------------------------------------------------------------------ V
目錄 ------------------------------------------------------------------------ VI
圖目錄 ------------------------------------------------------------------------ XII
表目錄 ------------------------------------------------------------------------ XVI
符號說明 ------------------------------------------------------------------------ XVII

一、緒論------------------------------------------------------------------- 1
二、文獻回顧--------------------------------------------------------------- 2
2.1 反應性染料簡介---------------------------------------------------------- 2
2.2 棉纖維用反應性染料的發展史----------------------------------------------- 2
2.3 反應性染料的基本結構介紹------------------------------------------------- 6
2.4 反應基種類簡介---------------------------------------------------------- 7
2.5 反應性染料使用的色母----------------------------------------------------- 13
2.6 反應性染料與棉纖維的化學反應機制------------------------------------------ 19
2.6.1 親核性取代反應---------------------------------------------------- 19
2.6.2 親核性加成反應---------------------------------------------------- 20
2.7 反應性染料在棉纖維的染色方法---------------------------------------------- 21
2.7.1 大浴比(long-liquor)染色或浸染(Exhaustion)染色---------------------- 21
2.7.1.1直染性S (Substantivity)----------------------------------------24
2.7.1.2吸盡性E (Exhaustion)------------------------------------------- 24
2.7.1.3反應率R (Reactivity) ------------------------------------------ 24
2.7.1.4固著率F ( % Fixation)------------------------------------------ 24
2.7.2 印花------------------------------------------------------------- 26
2.7.2.1 網版印花-------------------------------------------------------- 26
2.7.2.2 數位噴墨印花---------------------------------------------------- 27
2.7.3軋染-------------------------------------------------------------- 28
2.8 成功的反應性染料設計應考量因素------------------------------------------- 29
2.9 四級銨鹽活化三嗪反應性染料文獻回顧---------------------------------------- 30
三、研究背景與動機---------------------------------------------------------- 42
四、實驗------------------------------------------------------------------- 46
4.1 染料製備-------------------------------------------------------- 46
4.1.1 第一部分: 製備紅色反應性染料--------------------------------------- 46
4.1.1.1 5-氨基-4-羥基-3-[（1-磺基-2-萘基）偶氮]萘-2,7-二磺酸（紅色色母，見圖
50)的製備------------------------------------------------------- 55
4.1.1.2 5-[（4,6-二氯-1,3,5-三嗪-2-基）氨基] -4-羥基-3-[（1-硫代-2-萘基）
偶氮]萘-2,7-二磺酸（圖44，化合物(compound 4)，DCT染料）的製備------ 56
4.1.1.3 5-[[4-氯-6-（氰氨基）-1,3,5-三嗪-2-基]氨基] -4-羥基-3-[（1-硫代-2-
萘基）偶氮]萘-2 ，7-二磺酸(Red 1A)的製備--------------------------57
4.1.1.4 1- [4-（氰基氨基）-6-[[8-羥基-3,6-二磺基-7-[（1-磺基-2-萘基）偶氮]
-1-萘基]氨基] -1,3,5 -三嗪-2-基]吡啶-1--3-羧酸鹽（Red 1B）的製備--- 58
4.1.1.5 5-[（4-氯-6-甲氧基-1,3,5-三嗪-2-基）氨基] -4-羥基-3-[（1-硫代-2-
萘基）偶氮]萘-2,7 -二磺酸（Red 2A ）的製備------------------------ 59
4.1.1.6 1- [4-[[8-羥基-3,6-二磺基-7-[（1-磺基-2-萘基）偶氮] -1-萘基]氨基]
-6-甲氧基-1,3,5-三嗪 -2-基]吡啶-1--3-羧酸鹽（Red 2B）製備---------- 61
4.1.1.7 5-[[4-氯-6- [甲基（甲基磺酰基）氨基] -1,3,5-三嗪-2-基]氨基] -4-
羥基-3-[（1-磺基-2-萘基）偶氮 ]萘-2,7-二磺酸- ）（Red 3A ）的製備----63
4.1.1.8 1- [4-[[8-羥基-3,6-二磺基-7-[（1-磺基-2-萘基）偶氮] -1-萘基]氨基]
-6- [甲基（甲基磺酰基）氨基] -1 ，3,5-三嗪-2-基]吡啶-1--3-羧酸鹽
（Red 3B）的製備--------------------------------------------------64
4.1.1.9 5-[[4-氯-6-（N-甲基苯胺基）-1,3,5-三嗪-2-基]氨基] -4-羥基-3-[（1-
硫代-2-萘基）偶氮]萘 -2,7-二磺酸（Red 4A）的製備-------------------65
4.1.1.10 1- [4-[[8-羥基-3,6-二磺基-7-[（E）-（1-磺基-2-萘基）偶氮] -1-萘基]
氨基] -6-（N-甲基苯胺基） -1,3,5-三嗪-2-基]吡啶-1--3-羧酸鹽（Red 4B）
的製備-----------------------------------------------------------66
4.1.1.11 5-[（4-氯-6-羥基-1,3,5-三嗪-2-基）氨基] -4-羥基-3-[-（1-硫代-2-
萘基）偶氮]萘-2， 7-二磺酸（Red 5A）的製備-------------------------67
4.1.1.12 1- [4-羥基-6-[[8-羥基-3,6-二硫-7-[（E）-（1-硫-2-萘基）偶氮] -1-
萘基]氨基] -1,3 ，5-三嗪-2-基]吡啶-1--3-羧酸鹽（Red 5B）的製備----68

4.1.2 第二部分: 藍色及橘色反應性染料製備------------------------------------69
4.1.2.1 1- [4- [3-[（E）-[8-氨基-7-[（E）-（2,4-二硫代苯基）偶氮]]-1-羥基-
3,6-二硫代-2-萘基]偶氮 ] -4-磺基苯胺基] -6-（氰基氨基）-1,3,5-三嗪-
2-基]吡啶-1-基-3-羧酸(Blue-1B)的製備------------------------------74
4.1.2.2 5-氨基-3-[（E）-[5-[[4-氯-6- [3-（2-磺氧基乙基磺醯基）苯胺基]苯胺基]
-1,3,5-三嗪-2-基]氨基] -2- 磺-苯基]偶氮] -6-二氮烯基-4-羥基-萘-2,7-
二磺酸;苯-1,3-二磺酸(Blue-1C)的製備--------------------------------76
4.1.2.3 1- [4-（氰氨基）-6-[[6-[（E）-（1,5-二硫-2-萘基）偶氮] -5-羥基-7-磺
基-2-萘基]氨基] -1 ，3,5-三嗪-2-基]吡啶-1-3-羧酸鹽(Orange 1B)的製備-76
4.1.2.4 C.I. Reactive Orange 122--------------------------------------- 78
4.1.2.5 2,7-萘二磺酸，5-[[4-氯-6-[[3-[[2-（磺氧基）乙基]磺醯基]苯基]氨基]
-1,3,5-三嗪-2-基]氨基 ] -4-羥基-3-[（1-磺基-2-萘基）偶氮]-四鈉鹽
(Red 1C, CAS number: 80162-04-5)的製備----------------------------78
4.2 分析儀器------------------------------------------------------------------79
4.2.1可見光吸收光譜(UV-Visible Absorption Spectroscopy)--------------------79
4.2.2 薄層色譜法(Thin Layer Chromatography)--------------------------------79
4.2.3元素分析(Elemental Aanlysis)------------------------------------------79
4.2.4 高效液相色譜法(High Performance Liquid Chromatography----------------79
4.2.5 高解析質譜(High Resolution MASS Spectroscopy)------------------------79
4.2.6核磁共振儀(Nuclear Magnetic Resonance Spectroscopy)-------------------80
4.2.7傅立葉轉換紅外光譜儀( Fourier Transform Infrared, FTIR)----------------80
4.2.8分子電腦模擬----------------------------------------------------------80
4.3 化學品及棉花纖維來源--------------------------------------------------------81
4.4 測定染料有效成分含量--------------------------------------------------------81
4.5 染料水解動力學研究----------------------------------------------------------82
4.5.1第一部分: 10支紅色反應性染料水解常數研究---------------------------------82
4.5.2第二部分:藍色及橘色反應性染料水解常數研究--------------------------------82
4.6 冷軋堆(Cold pad‒batch)染色應用----------------------------------------------83
4.6.1染布色強度K/S值及L*a*b*值量測------------------------------------------83
4.6.2染深性(Build up)------------------------------------------------------83
4.6.3 30 g/L染色固著率(% Fixation)-----------------------------------------84
4.6.4染色強度與軋染時間依存性-----------------------------------------------85
4.6.5水洗色牢度------------------------------------------------------------85
4.6.6水牢度----------------------------------------------------------------85
五、結果和討論-----------------------------------------------------------------86
5.1 間-羧基吡啶(菸鹼酸四級胺鹽)三嗪反應性染料(m-carboxypyridium triazinyl reactive
dyes, NTR染料)反應機制----------------------------------------------------86
5.2 染料光學性質---------------------------------------------------------------91
5.3 染料有效純度與含量----------------------------------------------------------92
5.4 染料化學結構解析------------------------------------------------------------92
5.4.1 Red base紅色色母(Compound 3)結構(圖67)--------------------------------93
5.4.2 Red 1A染料結構解析----------------------------------------------------96
5.5 染料水解動力學研究--------------------------------------------------------- 100
5.5.1 原理及目的---------------------------------------------------------- 100
5.5.2 第一部份:紅色反應性染料水解動力學研究---------------------------------- 101
5.5.3 第二部分:藍色及橘色反應性染料水解動力學研究-----------------------------109
5.6 棉纖維冷軋堆染色應用實驗-----------------------------------------------------111
5.6.1 第一部份: 10支紅色反應性染料染色性--------------------------------------111
5.6.1.1 冷軋堆染色染深性(build-up)-------------------------------------------109
5.6.1.2冷軋捲堆染色固色率(% Fixation)----------------------------------------117
5.6.1.3染色最佳上色值與冷軋堆時間依存性---------------------------------------119
5.6.1.4 Red 1~4A & Red 1~5B同染色深度色域圖----------------------------------124
5.6.1.5染色織物水洗牢度及水牢度-----------------------------------------------124
5.6.1.6分子電子密度模擬及哈米特取代基常數meta -------------------------------127
5.6.2第二部分: 紅、藍、橘之NHCN/Nic反應基染料染深性----------------------------130
5.6.2.1 Red 1B 與Red 1C冷軋堆染深性比較---------------------------------------130
5.6.2.2 Blue 1B與Blue 1C冷軋堆染深性比較-------------------------------------131
5.6.2.3 Orange 1B與C. I. Reactive Orange 122冷軋堆染深性比較-----------------132
5.7 設計合適的NTR染料應用於冷軋捲堆染程--------------------------------------------133

六、結論與未來展望---------------------------------------------------------------135

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指導教授

吳春桂

審核日期

2021-7-9

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