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

作　　者：Xiao-Jun Zhao Zhi-Hua Cui Ren-Liang Wang Xin Li Su-Ju Fan Wei-Guo Chen 

机构地区：[1]Engineering Research Center for Eco-Dyeing & Finishing of Textiles,Ministry of Education of China [2]Key Laboratory of Advanced Textile Materials and Manufacturing Technology,Ministry of Education of China [3]Zhejiang Longsheng Group Co.,Ltd.

出　　处：《Chinese Chemical Letters》2015年第2期259-262,共4页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.21106135 and 51173168);Zhejiang Provincial Key Innovation Team(No.2010R50038);Zhejiang Provincial Top Key Academic Discipline of Chemical Engineering and Technology;"521" Talent Project of Zhejiang Sci-Tech University

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℃,10 h） were provided.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℃,10 h） were provided.

关 键 词：Aromatic primary amine Wet fastness Mannich reaction Acid dye Silk 

分 类 号：TQ610[化学工程—精细化工]