Synthesis,spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers  

作　　者：Zhi Hua Cui Xi Dong Wang Jiang Chao Guo Wei Guo Chen 

机构地区：[1]Key Laboratory of Advanced Textile Materials and Manufacturing Technology,Ministry of Education of China,Zhejiang Sci-Tech University,ChinaHangzhou 310018 [2]Engineering Research Center for Eco-Dyeing&Finishing of Textiles,Ministry of Education,Zhejiang Sci-Tech University,ChinaHangzhou 310018

出　　处：《Chinese Chemical Letters》2012年第9期1019-1022,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 Natural Science Foundation of China(Nos.Y4090227 and Y5080021);Zhejiang Provincial Key Innovation Team(No.2010R50038)

摘　　要：Two novel N-heterocycle-containing benzotriazole compounds, 5-（5-chloro-2-benzotriazolyl）-6-hydroxy-l,4-dimethyl-3-car- bonitrile-2-pyddone （2） and 4-（5-chloro-2-benzotdazolyl）-5-methyl-2-phenyl-3-pyrazolone （4）, were synthesized from reactant 4- chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by Fr-IR, 1H NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion.Two novel N-heterocycle-containing benzotriazole compounds, 5-（5-chloro-2-benzotriazolyl）-6-hydroxy-l,4-dimethyl-3-car- bonitrile-2-pyddone （2） and 4-（5-chloro-2-benzotdazolyl）-5-methyl-2-phenyl-3-pyrazolone （4）, were synthesized from reactant 4- chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by Fr-IR, 1H NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion.

关 键 词：BENZOTRIAZOLE UV absorber PYRAZOLONE PYRIDONE Anti-UV protection 

分 类 号：TQ314.257[化学工程—高聚物工业] O626.26[理学—有机化学]