Journal of Textile Research ›› 2019, Vol. 40 ›› Issue (11): 100-105.doi: 10.13475/j.fzxb.20181104407

• Dyeing and Finishing & Chemicals • Previous Articles     Next Articles

Diazotization-coupling dyeing and process control of silk fabrics by primary aryl amine dyes

JIANG Hua1,2(), ZHANG Zhiheng1, CAI Jinfang1, CHEN Weiguo1,2, CUI Zhihua1,2, SUN Yanfeng3   

  1. 1. Engineering Research Center for Eco-Dyeing and Finishing of Textiles, Ministry of Education, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, China
    2. Key Laboratory of Advanced Textile Materials and Manufacturing Technology, Ministry of Education, Hangzhou, Zhejiang 310018, China
    3. Zhejiang Jihua Group Co., Ltd., Hangzhou, Zhejiang 311227, China
  • Received:2018-11-16 Revised:2019-04-03 Online:2019-11-15 Published:2019-11-26

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Abstract:

In order to improve the fastness property of dyed silk fabrics, primary aryl amine dyes were selected for dyeing silk fabrics by a diazotization-coupling dyeing process. The dyeing conditions, such as dyeing temperature, pH value and concentration of sodium sulfate were optimized and the mechanism of color change before and after dyeing was discussed. The application scope of dyes was explored. The results showed that the K/S values of dyed fabrics are greatly increased when primary aryl amine dyes and silk fabrics are heated in one bath followed by diazotization of dyes and coupling with silk at low temperature. The reason for color change of dyed silk fabrics originates from the change of dye molecular conjugation leading to the variation of chromophore's band gap. Aniline, naphthylamine and 1-aminoanthraquinone dyes can be applied in this reactive dyeing method. The washing fastness and rubbing fastness of dyed silk fabrics could reach above grade 4.

Key words: silk fabric, primary aryl amine dye, diazotization-coupling reaction, dyeing property, color fastness

CLC Number: 

  • TS193.5

Fig.1

Chemical structures of primary aryl amine dyes. (a) C.I. Acid Brown 4; (b) D1; (c) C.I. Blue 40; (d) C.I. Acid Green 20"

Fig.2

K/S value curves of dyed silk fabrics by diazotization-coupling coloration"

Fig.3

Effect of dyeing temperature on K/S value of dyed silk fabrics"

Fig.4

Effect of pH value of dye bath on K/S value of dyed silk fabrics"

Fig.5

Effect of mass concentration of sodium sulfate on K/S value of dyed silk fabrics"

Fig.6

K/S value curves of dyed silk fabrics by C.I. Acid Brown 4 and that of after extraction treatment"

Fig.7

Energy level calculation of C.I. Acid Brown 4 and its related simulacrum of dyeing product"

Fig.8

K/S value curves of dyed silk fabrics by diazotization-coupling coloration and under conventional acid condition. (a) D1; (b) C.I. Acid Blue 40; (c) C.I. Acid Green 20"

Tab.1

Diazotization-coupling dyeing properties of silk fabrics dyed by primary aryl amine dyes"

染料 上染率/% 固色率/% K/S值 L* a* b*
C.I.酸性棕4 85 82 15.77 25.38 22.75 -0.07
染料D1 90 97 19.30 21.90 19.20 5.74
C.I.酸性蓝40 84 29 3.68 42.13 6.74 20.36
C.I.酸性绿20 81 93 18.96 24.42 -8.38 -6.53

Tab.2

Color fastnesses of silk fabrics dyed by diazotization-coupling coloration method 级"

染料 耐皂洗色牢度 耐摩擦色牢度
变色 沾色 干 湿
丝 棉
C.I.酸性棕4 4~5 4~5 4~5 5 4~5
染料D1 4~5 4 4~5 5 4~5
C.I.酸性蓝40 5 4~5 4~5 4~5 4
C.I.酸性绿20 4~5 4~5 5 5 4~5
[1] 张红燕, 吴彬, 蔡宇, 等. 酸性染料固色剂TF-506S的合成及性能研究[J]. 印染助剂, 2010,27(9):36-38.
ZHANG Hongyan, WU Bin, CAI Yu, et al. Study on the synjournal and the properties of acid dyes fixing agent TF-506S[J]. Textile Auxiliaries, 2010,27(9):36-38.
[2] CUI J, ZHANG S F. Synjournal and application of a novel, triphendioxazine-based, phosphorus-containing acid dye for wool[J]. Coloration Technology, 2018,134(5):381-389.
[3] 章杰. 现代活性染料技术进展[J]. 上海化工, 2000,24:21-26.
ZHANG Jie. Technical progress in modern reactive dyestuffs[J]. Shanghai Chemical Industry, 2000,24:21-26.
[4] 郭文登, 莫杨, 黄益, 等. 真丝绸数码印花活性染料墨水性能测试与评估[J]. 丝绸, 2018,55(9):1-6.
GUO Wendeng, MO Yang, HUANG Yi, et al. Performance testing and evaluation of reactive dye inks for silk digital printing[J]. Journal of Silk, 2018,55(9):1-6.
[5] 卢声, 林杰, 程德红, 等. 活性染料水解对棉织物染色性能的影响[J]. 纺织学报, 2014,35(9):95-99.
LU Sheng, LIN Jie, CHENG Dehong, et al. Influence of hydrolysis of reactive dye on dyeing property of cotton fabrics[J]. Journal of Textile Research, 2014,35(9):95-99.
[6] MURPHY A R, JOHN P S, KAPLAN D L. Modification of silk fibroin using diazonium coupling chemistry and the effects on hMSC proliferation and differentiation[J]. Biomaterials, 2008,29(19):2829-2838.
doi: 10.1016/j.biomaterials.2008.03.039 pmid: 18417206
[7] JOSHI N S, WHITAKER L R, FRANCIS M B. A three-component mannich-type reaction for selective tyrosine bioconjugation[J]. Journal of The American Chemical Society, 2004,126(49):15942-15943.
pmid: 15584710
[8] CSEREP G B, HERNER A, WOLFBEIS O S, et al. Tyrosine specific sequential labeling of proteins[J]. Bioorganic & Medicinal Chemistry Letters, 2013,23(21):5776-5778.
doi: 10.1016/j.bmcl.2013.09.002 pmid: 24075730
[9] JAKUBOWSKI N, MESSERSCHMIDT J, ANORBE M G, et al. Labelling of proteins by use of iodination and detection by ICP-MS[J]. Journal of Analytical Atomic Spectrometry, 2008,23(11):1487-1496.
doi: 10.1039/b718074h
[10] CHEN W, WANG Z, CUI Z, et al. Study on coloration of silk based on coupling reaction with a diazonium compound[J]. Fibers and Polymers, 2014,15(5):966-970.
doi: 10.1007/s12221-014-0966-5
[11] XU D, LI Z, PENG Y X, et al. Post-modification of 2-formylthiophene based heterocyclic azo dyes[J]. Dyes and Pigments, 2016,133:143-152.
[12] BHATE P M, DEVI R V, DUGANE R, et al. A novel reactive dye system based on diazonium salts[J]. Dyes and Pigments, 2017,145:208-215.
[13] 杨海伟, 王宗乾, 徐晶晶, 等. 蚕丝丝素酪氨酸残基的偶合修饰与工艺调控[J]. 纺织学报, 2018,39(9):102-108.
YANG Haiwei, WANG Zongqian, XU Jingjing, et al. Coupling modification and process regulation of tyrosine residues on silk fibroin[J]. Journal of Textile Research, 2018,39(9):102-108.
[14] 孙剑飞, 江华, 崔志华, 等. 双亚芴基醌式噻吩型酸性染料对羊毛织物和桑蚕丝织物的染色性能对比研究[J]. 毛纺科技, 2018,46(5):31-36.
SUN Jianfei, JIANG Hua, CUI Zhihua, et al. Comparative study on dyeing property of difluorenylidene quinoidal thiophene type acid dye on wool and silk fabrics[J]. Wool Textile Journal, 2018,46(5):31-36.
[15] 杨志斌, 万红. H-酸重氮盐自偶联反应及其分析应用研究[J]. 分析化学, 1992,20(7):816-818.
YANG Zhibin, WAN Hong. Reaction and application of nitrite with H-acid[J]. Chinese Journal of Analytical Chemistry, 1992,20(7):816-818.
[16] 胡倩, 蔡金芳, 江华, 等. 芳伯胺染料对棉织物反应性染色工艺及机理[J]. 浙江理工大学学报, 2018,39(5):533-538.
HU Qian, CAI Jinfang, JIANG Hua, et al. Reactive dyeing process and mechanism of primary arylamine dyes to cotton fabrics[J]. Journal of Zhejiang Sci-Tech University, 2018,39(5):533-538.
[17] 苏秋宁, 唐辉, 刘志达. 重氮化反应及其应用[J]. 精细化工中间体, 2012,42(3):13-16.
SU Qiuning, TANG Hui, LIU Zhida. The synjournal and application of diazonium[J]. Fine Chemical Intermediates, 2012,42(3):13-16.
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