JOURNAL BROWSE
Search
Advanced SearchSearch Tips
Synthesis, Structure Investigation and Dyeing Assessment of Novel Bisazo Disperse Dyes Derived from 3-(2'-Hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
 Title & Authors
Synthesis, Structure Investigation and Dyeing Assessment of Novel Bisazo Disperse Dyes Derived from 3-(2'-Hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones
Metwally, M.A.; Bondock, S.; El-Desouky, S.I.; Abdou, M.M.;
  PDF(new window)
 Abstract
In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones . Compounds were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives . The latter products as well as spectral data indicated that compounds exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes and were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates (, , , , *) was assessed.
 Keywords
Bisazo pyrazolin-5-ones;Azo-hydrazone tautomerism;Fastness properties;CIELAB coordinates;
 Language
English
 Cited by
1.
Synthesis, Spectral Property and Dyeing Assessment of Azo Disperse Dyes Containing Carbonyl and Dicyanovinyl Groups,;;;;;;;

Bulletin of the Korean Chemical Society, 2013. vol.34. 3, pp.863-867 crossref(new window)
1.
Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions, Arabian Journal of Chemistry, 2015  crossref(new windwow)
2.
Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity, Arabian Journal of Chemistry, 2015  crossref(new windwow)
3.
Advancements in tetronic acid chemistry. Part 2: Use as a simple precursor to privileged heterocyclic motifs, Molecular Diversity, 2016, 20, 4, 989  crossref(new windwow)
4.
Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions, Arabian Journal of Chemistry, 2015  crossref(new windwow)
5.
Stability of Dye Dispersions in the Presence of Some Eco-Friendly Dispersing Agents, Journal of Surfactants and Detergents, 2013, 16, 6, 849  crossref(new windwow)
6.
Synthesis, Spectral Property and Dyeing Assessment of Azo Disperse Dyes Containing Carbonyl and Dicyanovinyl Groups, Bulletin of the Korean Chemical Society, 2013, 34, 3, 863  crossref(new windwow)
7.
A facile synthesis and tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes, Coloration Technology, 2013, 129, 6, 418  crossref(new windwow)
 References
1.
Annen, O.; Egli, R.; Hasler, R.; Henzi, B.; Jakob, H.; Matzinger, P. Rev. Prog. Coloration 1987, 17, 72.

2.
Metwally, M. A.; Bondock; S.; El-Desouky; S. I.; Abdou; M. M. Int. J. Modern Org. Chem. 2012, 1, 19.

3.
Karci, F.; Ertan, N. Dyes Pigm. 2002, 55, 99. crossref(new window)

4.
Ho, Y. W. Dyes Pigm. 2005, 64, 223. crossref(new window)

5.
Ozdemir, A.; Turan-Zitouni, G.; AslmKaplanclkll, Z.; Revial, G.; Demirci, F.; Iscan, G. J Enzyme Inhib. Med. Chem. 2010, 25, 565. crossref(new window)

6.
Kucukguzel, S. G.; Rollas, S. Farmaco 2002, 57, 583. crossref(new window)

7.
Kucukguzel, S. G.; Rollas, S.; Erdeniz, H.; Kiraz, M.; Cevdet Ekinci, A.; Vidin, A. Eur. J. Med. Chem. 2000, 35, 761. crossref(new window)

8.
Minkin, V. I.; Garnovskii, A. D.; Elguero, J.; Katritzky, A. R.; Denisko, O. V. Adv. Heterocycl. Chem. 2000, 76, 157. crossref(new window)

9.
Whitaker, A. Acta crystallogr. 1988, C44, 1767.

10.
Whitaker, A. Acta crystallogr. 1988, C44, 1587.

11.
Connor, J. A.; Kennedy, R. J.; Dawies, H. M.; Hursthouse, M. B.; Walker, N. P. C. J. Chem. Soc., Perkin Trans. 1990, 2, 203.

12.
Whitaker, A. J. Soc. Dyers Colour 1995, 11, 66.

13.
Emeleus, L. C.; Cupertino, D. C.; Harris, S. G.; Owens, S.; Parsons, S.; Swart, R. W.; Tasker, P. A.; White, D. J. J. Chem. Soc., Dalton Trans. 2001, 2, 1239.

14.
Sawicki, E. J. Org. Chem. 1957, 22, 915. crossref(new window)

15.
Sawicki, E. J. Org. Chem. 1957, 22, 1084. crossref(new window)

16.
Lycka, A.; Machacek, V. Dyes Pigm. 1986, 7, 171. crossref(new window)

17.
Ueno, K. J. Am. Chem. Soc. 1957, 79, 3205. crossref(new window)

18.
Burawoy, A.; Thompson, A. R. J. Chem. Soc. 1953, 1443. crossref(new window)

19.
Hadzi, D. J. Chem. Soc. 1956, 2143. crossref(new window)

20.
Ospenson, J. Acta Chem. Scand. 1951, 5, 491. crossref(new window)

21.
Metwally, M. A.; Bondock, S.; El-Desouky, S. I.; Abdou, M. M. J. Korean Chem. Soc. 2012, 56, 82. crossref(new window)

22.
Metwally, M. A.; Bondock, S.; El-Desouky, S. I.; Abdou, M. M. Dyes Pigm. 2012 (submitted).

23.
Perrin, D. D.; Armarego, W. L. F.; Parris, D. R. Purification of laboratory chemicals, 2nd ed.; Pergamon: New York, 1980.

24.
Shawali, A. S.; Harb, N. M. S.; Badahdah, K. O. J. Heterocycl. Chem. 1985, 22, 1397. crossref(new window)

25.
Anonymous. Standard methods for the determination of the color fastness of textiles and leather, 5th ed.; The Society of Dyers and Colorists: Bradford, England, 1990; p 619.

26.
Yasuda, H.; Nidokawa, H. J. Org. Chem. 1966, 31, 1722. crossref(new window)

27.
Jones, R.; Ryan, A. J.; Sternhell, S.; Wright, S. E. Tetrahedron 1963, 19, 1497. crossref(new window)

28.
Geissman, T. A.; Armen, A. J. Am. Chem. Soc. 1955, 77, 1623. crossref(new window)

29.
Russell, P. E. J. Am. Chem. Soc. 1953, 75, 5315. crossref(new window)

30.
Randall, H. M.; Fuson, N.; Fowler, R. G.; Dangl, J. R. Infrared determination of organic compounds; D. Van Nostrand, Co., Inc.: New York, 1949; p 222.

31.
Gagnon, P. E.; Boivin, J. L.; MacDonald, B. R.; Yaffe, L. Can. J. Chem. 1954, 32, 823. crossref(new window)

32.
Colthup, N. B. J. Opt. Soc. Am. A. 1950, 40, 397. crossref(new window)

33.
Bellamy, L. J. Adv. Infrared group frequencies; Methuen: London, 1968; p 52.

34.
Yasuda, H. Bull. Chem. Soc. Jap. 1967, 40, 1239. crossref(new window)

35.
Oakes, J.; Gratton, P. J. Chem. Soc., Perkin Trans. 1998, 2, 1857.

36.
Brode, W.; Herdle, L. J. Org. Chem. 1941, 6, 713. crossref(new window)

37.
Lestina, G. J.; Regan, T. H. J. Org. Chem. 1969, 34, 1685. crossref(new window)

38.
Yoder, C. H.; Barth, R. C.; Richter, W. M.; Snavely, F. A. J. Org. Chem. 1972, 37, 4121. crossref(new window)

39.
Snavely, F. A.; Yoder, C. H. J. Org. Chem. 1968, 33, 513. crossref(new window)

40.
Chakravorty, A.; Ktlia, K. C. J. Org. Chem. 1970, 35, 2231. crossref(new window)

41.
Bellamy, L. J. The infrared spectra of complex molecules; Chapman and Hall: London, 1975; p 303.

42.
SDL. Atlas Ltd. P.O. Box 162, Crown Royal, Shawcross St., Stockport SK1 3JW.

43.
Gordon, P. F.; Gregory, P. Organic Chemistry in Color; Springer-Verlag: Berlin, 1983; p 289.