Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis, Spectral Property and Dyeing Assessment of Azo Disperse Dyes Containing Carbonyl and Dicyanovinyl Groups

  • Choi, Yun Seok (Department of Biological Chemistry, University of Science and Technology) ;
  • Lee, Kun Su (Central Research Institute, KISCO's Research Institute, Kyung-In Synthetic Corporation) ;
  • Kim, Hye Jin (Central Research Institute, KISCO's Research Institute, Kyung-In Synthetic Corporation) ;
  • Choi, Jong Yun (Central Research Institute, KISCO's Research Institute, Kyung-In Synthetic Corporation) ;
  • Kang, Soon Bang (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Lee, Eui Jae (Central Research Institute, KISCO's Research Institute, Kyung-In Synthetic Corporation) ;
  • Keum, Gyochang (Department of Biological Chemistry, University of Science and Technology)
  • Received : 2012.11.19
  • Accepted : 2012.12.19
  • Published : 2013.03.20
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Abstract

A series of azo disperse dyes having dicyanovinyl groups was synthesized by the Knoevenagel condensation with malononitrile from carbonyl substituted phenylazo disperse dyes which were prepared by conventional diazo coupling reaction of aniline derivatives as diazo components. A variety of coupling components such as anilines, an indole and a pyridone were used. The azo disperse dyes were evaluated for their spectral properties and dyeing assessment on the polyester fabrics. The azo disperse dyes containing dicyanovinyl groups showed bathochromic shifts and darker colors due to increased electron withdrawing strength in their azo components and extended conjugation by dicyanovinyl groups than their parent carbonyl substituted azo dyes. The dyes containing 2-acetylamino-5-methoxy substituent in the coupling component exhibited higher wavelength of maximum absorbance (${\lambda}_{max}$) and significant negative solvatochromism than those of other dyes due to intramolecular hydrogen bonding.

Keywords

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