Synthesis of Metal Complexes of Some Formazans Obtaining From Cinnamaldehyde and Investigation of Their Dyeing Properties Using Different Methods

Year 2018, Issue: 14, 315 - 322, 31.12.2018

Nursabah Sarıkavaklı , Fatma Erol

https://doi.org/10.31590/ejosat.442722

Abstract

In this study, two formazans were synthesized by coupling cinnamaldehyde phenyl hydrazone which was obtained by activation of cinnamaldehyde with phenylhydrazone, with diazonium salts of anthranilic acid and sulfonilic acid. The complexes of Co⁺², Ni⁺², Cu²⁺ salts of these formazans were also synthesized. These compounds were characterized by elemental analysis, infrared (IR), ultraviolet–visible (UV–vis),¹H nuclear magnetic resonance (¹H-NMR) and  ¹³C-NMR spectra datas. Investigation of availability of these compounds as dyes were carried out for this purpose. In the present experimental approach, we applied two methods; The first one was direct dyeing with these complexes, and the other one was complex formation on the fibres. Finally, an investigation was carried out  for the fastness values (test) and it was found higher values, which was quite better and different from the other workers / researcher working in the same field.

Keywords

Formazans, Metal complexes, Dyeing, Fastness properties, Polyamide fibres

Synthesis of Metal Complexes of Some Formazans Obtaining From Cinnamaldehyde and Investigation of Their Dyeing Properties Using Different Methods

Abstract

In this study,
two formazans were synthesized by coupling cinnamaldehyde phenyl hydrazone
which was obtained by activation of cinnamaldehyde with phenylhydrazone, with
diazonium salts of anthranilic acid and sulfonilic acid. The complexes of Co⁺²,
Ni⁺², Cu²⁺ salts of these formazans were also
synthesized. These compounds were characterized by elemental analysis, infrared
(IR), ultraviolet–visible (UV–vis),¹H nuclear magnetic resonance (¹H-NMR) and  ¹³C-NMR spectra datas. Investigation of availability of
these compounds as dyes were
carried out for this purpose. In the present experimental approach, we
applied two methods; The first one was direct dyeing with these complexes, and
the other one was complex formation on the fibres. Finally, an
investigation was carried out  for the fastness
values (test) and it was found higher values, which was quite better and
different from the other workers / researcher working in the same field.

Keywords

Formazans, Metal complexes, Dyeing, Fastness properties

References

• Lewis, J.W., Sandorfy,C. 1983. Infrared-absorptıon and resonance raman-scatterıng of photochromıc trıphenylformazans. Canadıan Journal of Chemıstry-Revue Canadıenne de Chımıe 61(5), 809-816.
• Katritzky, A.R. Belyakov, S.A. Cheng, D. Durst, H.D. 1995. Syntheses of formazans under phase-transfer condıtıons. Synthesıs-Stuttgart 5,577-581.
• Tezcan, H. Ozkan, N. 2003. Substituent effects on the spectral properties of some 3-substituted formazans. Dyes and Pıgments 56(2), 159-166.
• Tezcan, H. Şenöz, H. Tokay, N. 2012. Spectraland electrochemical behavior of 1-[(NO2, COOH)-substituted phenyl]-3,5-diphenylformazans. Monatsh Chem. 143, 579–588.
• Sherif, O.E. Issa, Y.M. Hassouna, M.E.M. 1993. Structural studies on 3-acetyl-1,5-diaryl and 3-cyano-1,5-diaryl formazan chelates with cerium(III), thorium(IV) and uranium(VI). Monatshefte für Chemie/Chemical Monthly. 124(6-7), 627–635.
• Brown, D.A. Bögge, H, Lipunova, G.N 1998. Iron and manganese complexes of benzothiazolylformazans. Inorg Chim Acta. 280, 30–38.
• Kawamura, Y. Yamauchi, J. Ohya-Nishiguchi H. 1993. Spectroscopıc and structural characterızatıon of formazanyl copper-complexes. Bulletın of the Chemıcal Socıety of Japan. 66(12), 3593-3599.
• Tezcan, H. Uzluk, E. 2008. The synthesis and spectroscopic characterization of Ni(II) complexes of 1-substituted phenyl-3,5-diphenylformazans. Dyes and Pigments. 77, 626-634.
• Szymczyk, M. Czajkowski, W. Stolarski, R. (1999). Iron complexed dyes based on 1,5-diaryl-3-cyanoformazanes. Dyes and Pigments, 42(3), 227–235.
• Czajkowski, W. Stolarski, R. Szymczyk, M. 2000. Studies on isomerism of 1:2 iron complexed dye based on 1-(5'-nitro-2'-hydroxyphenyl)-3-cyano-5-(4''-sulphonamidophenyl)formazan. Dyes and Pigments. 47(1-2), 143-149.
• Gök, Y. Tüfekci, M. Özcan, E. 1993. Synthesıs of novel homo and heterobımetallıc complexes of ferrocenyl formazans. Synthesıs and Reactıvıty ın Inorganıc and Metal-Organıc Chemıstry, 23(5),861-873.
• Uchiumi, A. Takatsu, A. Tanaka, H. 1991. Metal Complex Formatıon of Some Anthryl Formazans. Anal Sci, 7, 459–462.
• Szymczyk, M. El-Shafei, A. Freeman, H. S. 2007. Design, synthesis, and characterization of new iron-complexed azo dyes. Dyes and Pigments.72(1), 8-15.
• Lipunova, G. N. Petrova, I. G. Lipunov, I. N. 1997. Synthesis and complex-forming properties of polymeric formazans. Vysokomolekulyarnye Soedineniya, Seriya A i Seriya B. 39(9), 1523-1526.
• Sokolowska, G.J. Freeman, H.S. Reife, A. 1996. Synthetic dyes based on environmental considerations. Part 2:Iron complexed formazan dyes. Dyes and Pıgments. 30(1), 1-20.
• Sekar, N. 2001. Environmental friendly dyes-iron complexed formazan dye. Colourage, 48(9), 49-52.
• Schwaiger, G. Springer, H. Russ, W. 1988. Copper complex-formazan compounds, their preparation, and their use as dyes. Ger. Offen. 3705789 A1 19880901, 23.
• Tzikas, A. Klier, H. (2002). Reactive formazan complex green dyes, their production and their use. U.S, 6353094 B1 20020305, 25.
• Brinkmann, C. (1990) Fiber-reactive metal- complex formazan dye. Eur. Pat. Appl., 402318 A2 19901212, 23.
• Knudsen, H.H. Wenzel, H. 1996 Environmentally friendly method in reactive dyeing of cotton. Water Scıence and Technology. 33(6), 17-27.
• Oritani, T. Fukuhara, N. Okajima, T. 2004. Electrochemical and spectroscopic studies on electron-transfer reaction between novel water-soluble tetrazolium salts and a superoxide ion. Inorganıca Chımıca Acta. 357(2), 436-442.
• Ishıyama, M. Shıga, M. Sasamoto, K. 1993. A new sulfonated tetrazolıum salt that produces a hıghly water-soluble formazan dye. Chemıcal & Pharmaceutıcal Bulletın. 41(6),1118-1122.
• Weast, R.C. 1978. Handbook of Chemistry and Physics, USA, 59.334049
• Petrovanu, M. Borcea, A. 1958. Copper Complexes with some formazans, derived from the 0-, m-, p-aminobenzoic acids. Analele Stiint. Univ. Al.G.Cuza. 4(1),157-68.
• Badawy, S.S. Issa, Y.M. Abdel-Fattah, H.M. 1989. Thermogravimetric Studies on Lanthanide Complexes of New Derivatives of 1,5-Diaryl-3-Acetyl Formazan. Transition Met. Chem, 14, 401–406.
• Schiman, F. 1970. Nuclear magnetic resonance of complex molecules. Braunschweig. 1, 41-70.
• Tezcan, H. Uzluk, E. Aksu, M.L. 2008. Synthesis, spectroscopic and electrochemical studies on bis-[1,3-substituted (Cl, Br) phenyl-5-phenyl formazanato]nickel(II) complexes. Spectrochimica Acta Part A, 70, 973–982.
• Umemoto, K. 1989. Electrochemıcal studıes of the reductıon-mechanısm of tetrazolıum salts and formazans. Bull. Chem. Soc. Jpn., 62, 3783–3789.