苯并[a]吩恶嗪基功能染料制备及其在改性涤纶织物上的应用  

Preparation of benzo[a]phenoxazine based functional dyes and their application on modified polyester fabrics

作　　者：韩画宇 杨文龙 王甫 胡柳 胡毅[1] HAN Huayu;YANG Wenlong;WANG Fu;HU Liu;HU Yi(College of Textile Science and Engineering,Zhejiang Sci-Tech University,Hangzhou,Zhejiang 310018,China;Zhejiang Shengfa Textile Printing and Dyeing Co.,Ltd.,Huzhou,Zhejiang 313100,China;College of Chemistry and Chemical Engineering,Donghua University,Shanghai 201620,China)

机构地区：[1]浙江理工大学纺织科学与工程学院,浙江杭州310018 [2]浙江盛发纺织印染有限公司,浙江湖州313100 [3]东华大学化学与化工学院,上海201620

出　　处：《纺织学报》2024年第10期128-136,共9页Journal of Textile Research

基　　金：国家自然科学基金项目(22208310);中国博士后科学基金第74批面上资助项目(2023M743129)。

摘　　要：为通过简单的方法赋予阳离子可染改性涤纶织物功能性,合成了新型光功能性苯并[a]吩恶嗪基阳离子染料,将其应用于阳离子可染改性涤纶织物的染色,使染色织物兼具功能性。首先合成了5-二乙氨基-2-亚硝基苯酚盐酸盐中间体,进一步与盐酸萘乙二胺或N-丙基-1-萘胺经亲核取代反应,制备了5-乙二氨基-9-(二乙氨基)苯并[a]吩恶嗪氯化铵(N1)和5-丙氨基-9-(二乙氨基)苯并[a]吩恶嗪氯化铵(N2)2种染料。选取5-氨基-9-(二乙氨基)苯并[a]吩恶嗪硫酸铵(硫酸耐尔蓝,N3)作对比,探究3种染料的光物理化学性质及其对阳离子可染改性涤纶织物的染色性能,研究染色织物的荧光和光动力性能。结果表明:分子末端为丙氨基的染料N2对织物的上染率极高(99.65%),染色织物具有较好的匀染性,呈现强红色荧光,且各项色牢度均达到4~5级;3种染料染色织物均具有光驱动活性氧产生能力。Objective Functionally modified polyester textiles with high added value have significant development value in the fields of both domestic and industrial textiles.Cationic dyeable modified polyester fabrics are often endowed with enhanced functionality by coating and cross-linking with polymers.However,these modifications can compromise their breathability and adversely affect their apparent color and luster.This study aims to synthesize a novel photo-functional benzo[a]phenoxazine cationic dye,aim to achieve an integrated construction of both color and functionality on cationic dyeable modified polyester fabrics via a streamlined dyeing process.Method Two dyes,5-ethylenediamino-9-(diethylamino)benzo[a]phenoxazine ammonium chloride(N1)and 5-propylamino-9-(diethylamino)benzo[a]phenoxazine ammonium chloride(N2),were synthesized via nucleophilic substitution reactions.The structural characterizations of these dyes were accomplished using proton nuclear magnetic resonance(1H NMR)spectroscopy and Fourier transform infrared(FT-IR)spectroscopy.Additionally,5-amino-9-(diethylamino)benzo[a]phenoxazine ammonium sulfate(Nile Blue sulfate,N3)was selected as the comparative dye.The photophysical and chemical properties of these dyes,along with their dyeing performance on cationic dyeable modified polyester fabrics,were investigated using a color matching instrument,UV-visible spectrophotometer,and fluorescence spectrophotometer.The fluorescence emission and photodynamic properties of the dyed fabrics were also examined.Results This study was focused on two photo-functional benzo[a]phenoxazine cationic dyes for dyeing cationic dyeable modified polyester fabrics.1H NMR and FT-IR confirmed the successful synthesis of 5-ethylenediamino-9-(diethylamino)benzo[a]phenoxazine ammonium chloride(N1)and 5-propylamino-9-(diethylamino)benzo[a]phenoxazine ammonium chloride(N2).The maximum absorption wavelengths(λmax)of the three dyes in water were 648 nm,639 nm,and 635 nm,respectively,presenting a blue color.In DMF,bothλmax and the maximu

关 键 词：染色 苯并[a]吩恶嗪 功能染料 阳离子可染改性涤纶 荧光 光动力 

分 类 号：TQ614.2[化学工程—精细化工] TS193.1[轻工技术与工程—纺织化学与染整工程]