Citation: Xiao-Jun Zhao, Zhi-Hua Cui, Ren-Liang Wang, Xin Li, Su-Ju Fan, Wei-Guo Chen. Synthesis of an electron-rich aniline-containing dye and its dyeing behaviors on silk through a three-component Mannich-type reaction[J]. Chinese Chemical Letters, ;2015, 26(2): 259-262. doi: 10.1016/j.cclet.2014.11.002 shu

Synthesis of an electron-rich aniline-containing dye and its dyeing behaviors on silk through a three-component Mannich-type reaction

Xiao-Jun Zhao ^a ,
Zhi-Hua Cui ^a,b,, ,
Ren-Liang Wang ^c ,
Xin Li ^a ,
Su-Ju Fan ^a ,
Wei-Guo Chen ^a,b

1.
a Engineering Research Center for Eco-Dyeing & Finishing of Textiles, Ministry of Education of China, Hangzhou 310018, China;
2.
b Key Laboratory of Advanced Textile Materials and Manufacturing Technology, Ministry of Education of China, Hangzhou 310018, China;
c Zhejiang Longsheng Group Co.
c Zhejiang Longsheng Group Co., Ltd., Shangyu 312368, China

Corresponding author: Zhi-Hua Cui,
Received Date: 21 July 2014
Available Online: 21 October 2014
Fund Project: Zhejiang Provincial Top Key Academic Discipline of Chemical Engineering and Technology, and "521" Talent Project of Zhejiang Sci-Tech University. (No. 2010R50038)

Under the guidance of the finding that the tyrosine residues in proteins could undergo three-component Mannich-type reactions with formaldehyde and electron-rich aniline-containing compounds, which forms covalent bonding connections between the protein of interest and the aniline with high levels of selectivity under relatively mild conditions, an orange aromatic primary amine-containing acid dye AMODB was designed and readily synthesized. The molecular structure was characterized by FTIR, 1H NMR, mass spectrometry and elemental analysis. The synthesized dye and a similar control dye (C.I. Acid Yellow 11) without primary amine groups were applied to dye silk fabric by three dyeing processes: Mannich-type dyeing (with and without the addition of formaldehyde) and acidic dyeing. Their washing and rubbing fastness properties with different dyeing methods were examined and compared. It was found that the dyed silk fabric with AMODB by the Mannich-type dyeing showed higher color depth, better anti-stripping ability to DMF and better washing fastness than those of the dyed silk fabric with C.I. Acid Yellow 11 by acidic dyeing due to the covalent bond formation between the dye chromophore of AMODB and silk fiber. In addition, mild Mannich dyeing conditions suitable for silk (AMODB at 3% owf, 75:1 liquor-to-goods ratio, dyebath pH 5.5, 30 8C, 10 h) were provided.
- Aromatic primary amine,
- Wet fastness,
- Mannich reaction,
- Acid dye,
- Silk
1. [1]
  [1] C. Solazzo, J.M. Dyer, S. Deb-Choudhury, Proteomic profiling of the photo-oxidation of silk fibroin: implications for historic tin-weighted silk, Photochem. Photobiol. 88 (2012) 1217-1226.
2. [2]
  [2] J. Shao, J. Liu, J. Zheng, C.M. Carr, X-ray photoelectron spectroscopic study of silk fibroin surface, Polym. Int. 51 (2002) 1479-1483.
3. [3]
  [3] Z. Cai, Fiber Chemistry and Physics, China Textile & Apparel Press, Beijing, 2004.
4. [4]
  [4] G. Mitra, S.K. Bhattacharya, P.K. Mazumdar, A review on chemical processing of silk, Colourage 56 (2009) 48-50, 52.
5. [5]
  [5] S. Shakra, S. Shakra, E.E. Allam, H.F. Mansour, Dyeing natural silk fabrics-part I: direct dyes, Am. Dyest. Rep. 88 (1999) 29-32.
6. [6]
  [6] J. He, Dye Chemistry, China Textile & Apparel Press, Beijing, 2009.
7. [7]
  [7] M. Inoue, F. Okada, A. Sakurai, M. Sakakibara, A new development of dyestuffs degradation system using ultrasound, Ultrason. Sonochem. 13 (2006) 313-320.
8. [8]
  [8] S.K. Kansal, M. Singh, D. Sud, Studies on photodegradation of two commercial dyes in aqueous phase using different photocatalysts, J. Hazard. Mater. 141 (2007) 581-590.
9. [9]
  [9] S. Vanhulle, E. Enand, M. Trovaslet, Overlap of laccases/cellobiose dehydrogenase activities during the decolourization of anthraquinonic dyes with close chemical structures by Pycnoporus strains, Enzym. Microb. Technol. 40 (2007) 1723-1731.
10. [10]
  [10] J.H. Zheng, J.Z. Shao, J.Q. Liu, Study on the distribution of tyrosine in silk fibroin, J. Text. Res. 22 (2001) 7-9.
11. [11]
  [11] H.M. Zhou, H.R. Wang, Chemical Modification of Protein, Qinghua University, Beijing, 1998.
12. [12]
  [12] W. Chen, Z. Wang, Z. Cui, et al., Study on coloration of silk based on coupling reaction with a diazonium compound, Fibers Polym. 15 (2014) 966-970.
13. [13]
  [13] J. Gavrilyuk, H. Ban, M. Nagano, W. Hakamata, C.F. Barbas, Formylbenzene diazonium hexafluorophosphate reagent for tyrosine-selective modification of proteins and the introduction of a bioorthogonal aldehyde, Bioconj. Chem. 23 (2012) 2321-2328.
14. [14]
  [14] J.M. Hooker, E.W. Kovacs, M.B. Francis, Interior surface modification of bacteriophage MS2, J. Am. Chem. Soc. 126 (2004) 3718-3719.
15. [15]
  [15] T.L. Schlick, Z. Ding, E.W. Kovacs, M.B. Francis, Dual-surface modification of the tobacco mosaic virus, J. Am. Chem. Soc. 127 (2005) 3718-3723.
16. [16]
  [16] N.S. Joshi, L.R. Whitaker, M.B. Francis, A three-component Mannich-type reaction for selective tyrosine bioconjugation, J. Am. Chem. Soc. 126 (2004) 15942-15943.
17. [17]
  [17] D.W. Romanini, M.B. Francis, Attachment of peptide building blocks to proteins through tyrosine bioconjugation, Bioconj. Chem. 19 (2008) 153-157.
18. [18]
  [18] J.M. McFarland, N.S. Joshi, M.B. Francis, Characterization of a three-component coupling reaction on proteins by isotopic labeling and nuclear magnetic resonance spectroscopy, J. Am. Chem. Soc. 130 (2008) 7639-7644.
19. [19]
  [19] J. Yang, Analysis and Anatomy of Dyes, Chemical Industry Press, Beijing, 1989.
20. [20]
  [20] K. Hunger, Industrial Dyes: Chemistry, Properties, Applications, Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim, 2003.
1. [1]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
2. [2]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
3. [3]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
4. [4]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
5. [5]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
6. [6]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
7. [7]
  Nana Yang , Rui Yuan , Xinyue Fu , Xiao Tian , Jin Yu , Shengzhou Ma , Liuqing Wen , Jiabin Zhang . Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy. Chinese Chemical Letters, 2025, 36(8): 110757-. doi: 10.1016/j.cclet.2024.110757
8. [8]
  Meihui Cai , Yi Huang , Xingxing Ma , Qiuling Song . Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction. University Chemistry, 2025, 40(11): 184-190. doi: 10.12461/PKU.DXHX202412054
9. [9]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
10. [10]
  Xiaojuan Lv , Yuting Dong , Hongliang Huang , Dariusz W. Szczepanik , Naoki Aratani , Takahisa Ikeue , Feng Chen , Tao Zhang , Fengxian Qiu , Toshiharu Teranishi , Songlin Xue . Local aromatic ring cleaves the global aromatic ring in hexaphyrin(2.1.2.1.2.1). Chinese Chemical Letters, 2025, 36(7): 110435-. doi: 10.1016/j.cclet.2024.110435
11. [11]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
12. [12]
  Wenhao Wang , Guangpu Zhang , Qiufeng Wang , Fancang Meng , Hongbin Jia , Wei Jiang , Qingmin Ji . Hybrid nanoarchitectonics of TiO₂/aramid nanofiber membranes with softness and durability for photocatalytic dye degradation. Chinese Chemical Letters, 2024, 35(7): 109193-. doi: 10.1016/j.cclet.2023.109193
13. [13]
  Xiao-Fang Lv , Xiao-Yun Ran , Yu Zhao , Rui-Rui Zhang , Li-Na Zhang , Jing Shi , Ji-Xuan Xu , Qing-Quan Kong , Xiao-Qi Yu , Kun Li . Combing NIR-Ⅱ molecular dye with magnetic nanoparticles for enhanced photothermal theranostics with a 95.6% photothermal conversion efficiency. Chinese Chemical Letters, 2025, 36(4): 110027-. doi: 10.1016/j.cclet.2024.110027
14. [14]
  Qian ZHANG , Yuxuan ZHANG , Yongguang YANG , Ruijie BAI , Yuandong LI , Ling LI . FeMoS₄/carbon fiber cloth composites: Preparation and application in dye-sensitized solar cells. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1916-1926. doi: 10.11862/CJIC.20240442
15. [15]
  Yan-Ling Li , Yue Xu , Chen-Hong Wang , Rui Wang , Shuang-Quan Zang . Dye-stabilized atomically precise copper clusters for enhanced photocatalytic hydrogen evolution. Chinese Chemical Letters, 2025, 36(10): 111256-. doi: 10.1016/j.cclet.2025.111256
16. [16]
  Qingxuan Kong , Changwei Jiang , Bin Lyu , Zhaoting Li , Ning Jiao , Song Song . Denitrative iodination of nitroarenes with hydroiodic acid. Chinese Chemical Letters, 2025, 36(10): 111444-. doi: 10.1016/j.cclet.2025.111444
17. [17]
  Jian Yang , Guang Yang , Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267
18. [18]
  Xiao Yang , Wenjing Liu , Jiarui Kong , Xiangcheng Shan , Qiupei Lei , Zhipeng Yin , Runzeng Liu , Min Zhang , Qingzhe Zhang , Yongguang Yin , Chuanyong Jing , Yong Cai . Synthesis of amine-functionalized polystyrene resin-based globular adsorbents for efficient and selective removal of As and Sb species. Chinese Chemical Letters, 2025, 36(11): 110856-. doi: 10.1016/j.cclet.2025.110856
19. [19]
  Zi-Yi Yu , Gen-Feng Li , Zhe-Kun Xu , Lipeng Long , Yan Qin , Zi-Yi Du , Zhong-Xia Wang . Enantiomeric organic amine-borane adduct crystals with room-temperature multi-channel switches. Chinese Journal of Structural Chemistry, 2025, 44(11): 100715-100715. doi: 10.1016/j.cjsc.2025.100715
20. [20]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1120)
HTML views(13)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142