Advanced SearchSearch Tips
Synthesis and Properties of New Phthaloperinone Dyes containing Anthraquinone Moiety
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
  • Journal title : Textile Coloration and Finishing
  • Volume 28, Issue 2,  2016, pp.57-62
  • Publisher : The Korean Society of Dyers and Finishers
  • DOI : 10.5764/TCF.2016.28.2.57
 Title & Authors
Synthesis and Properties of New Phthaloperinone Dyes containing Anthraquinone Moiety
Jun, Kun; Gwon, Seon Yeong; Kim, Yu Jin; Kim, Sung Hoon;
  PDF(new window)
We have synthesized five novel phthaloperinone dyes via a condensation reaction to be applied as yellow colorants for liquid crystal display(LCD) color filters. The reaction between 1,8-naphthalic anhydride(1a), 4-chloro-1,8-naphthalic anhydride(1b), 4-bromo-1,8-naphthalic anhydride(1c), 3-nitro-1,8-naphthalic anhydride(1d), 4-nitro-1,8-naphthalic anhydride(1e) and 1,2-diaminoanthraquinone(2) proceeded readily giving a product in 72-88% yields. The synthesized dyes were characterized by UV-Vis, mass spectrometry and elemental analysis. The spectral properties and thermal stability of the dyes were examined. The dyes absorb at around 400-450nm. All five dyes showed satisfactory thermal stability: the dyes retain 99-100% of its original weight at , 98-100% at , 92-98% at , and 84-92% at . We have quantitatively evaluated the reaction mechanism and reactivity of dye molecules by means of Pariser-Parr-Pople Molecular Orbital Method(PPP-MO).
phthaloperinone;dyes;1,8-naphthalic anhydride;1,2-diaminoanthraquinone;TGA analysis;LCD color filter;Pariser-Parr-Pople Molecular Orbital Method(PPP-MO);
 Cited by
W. Herbst and K. Hunger, "Industrial Organic Pigment", Wiley-VCH, German, 2004.

A. Bistrzycki and J. Risi, Uber die Einwirkung verschiedener Diamine auf Naphtalsaure-anhydride, Helv. Chim. Acta, 8, 810(1925). crossref(new window)

E. Merian, Process for the Dyeing of Polyester Fibers, US Patent 2955902(1960).

D. Buffalo, Phthaloperinone Compounds, US Patent 3299065(1963).

S. Mitsutoshi, Photosensitive Member containing Phthaloperinone or Naphthalimede, US Patent 4988592(1991).

S. Ernest, Disperse Dyes of the Phthaloperinone Series, US Patent 3342818(1967).

P.Buecheler, Phthaloperinone Dyes and the Use Thereof for More Dyeing Plastics, US Patent 4417012A(1983).

W. D. Graham and H. H. Thomson, New Colouring Matters, US Patent 2889327A(1959).

R.W. Sabnis,Color Filter Technology for Liquid Crystal Display, Display, 20, 119(1999). crossref(new window)

K. Tsudaya, Color Filters for LCDs, Display,14,115(1993). crossref(new window)

P. Yeh and C. Gu, "Optics of Liquid Crystal Displays", John Wiley and Son, NY, 1999.

K.Jun, S. Y. Gwon, and S. H. Kim, Synthesis and Properties of New Phthaloperinone Dyes, Textile Coloration and Finishing, 27, 275(2015). crossref(new window)

B. Delley, An All-electron Numerical Method for Solving the Local Density Functional for Polyatomic Polecules, J. Chem. Phys., 92(1), 508(1990). crossref(new window)

B. Delley, From Moleculesto Solids with the $DMol_{3}$ Approach, J. Chem. Phys., 113(18), 7756(2000). crossref(new window)

A. D. Boese and N. C. Handy, A New Parametrization of Exchange-Correlation Generalized Gradient ApproximationFunctionals, J. Chem. Phys., 114(13), 5497(2001). crossref(new window)

K. Jun, S. Y. Gwon, and S. H. Kim, Relationship between the Molecular Structure and the Absorption Band Shape of Organic Dye, Textile Coloration and Finishing, 27, 270(2015). crossref(new window)