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
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