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

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

通讯作者: Zhi-Hua Cui,

基金项目:

Zhejiang Provincial Key Innovation Team (No. 2010R50038) (No. 2010R50038)

摘要: 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.

关键词:

English

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

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: 07 November 2014
Fund Project:

Abstract: 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.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

通讯作者: Zhi-Hua Cui,

English

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

Corresponding author: Zhi-Hua Cui,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

通讯作者: Zhi-Hua Cui,

English

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

Corresponding author: Zhi-Hua Cui,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

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