Synthesis Novel Compounds Include Diazo and Tetramine Groups and Investigated Dyeing Properties on Polyester Fabrics

Year 2014, Volume: 42 Issue: 3, 373 - 382, 01.09.2014

Naki Çolak Serkan Yavuz Bekir Sıtkı Çevrimli

Abstract

In this study, we have synthesized eight novel compounds used as dyes for polyester fabrics. Benzene-1,4- diamine, 4- 4-aminophenoxy benzenamine, 4- 4-aminophenylthio benzenamine and 4- 4-aminophenylsul- fonyl benzenamine were diazotized and coupled with malononitrile to give phenylazo malononitriles 1a-d . Then, including tetraminopyrazoles compounds 2a-d were synthesized by heating phenylazo malononitriles and hydrazine monohydrate in ethanol. The compounds were characterized by FT-IR, NMR spectroscopic tech- niques 1H NMR, 13C NMR and elementel analyses. UV-visible absorption spectra of the compounds are discus- sed 2a-d . The synthesized 1a-d and 2a-d were applied on polyester fabrics to investigated dyeing properties.

Keywords

Diazo dyes, polyester fabrics, malononitrile, dyeing properties

Diazo ve Tetraamin Grubu İçeren Yeni Bileşiklerin Sentezi ve Boyama Özelliklerinin Poliester Kumaşlar Üzerinde İncelenmesi

Abstract

B u çalışmada, polyester yapılar için kullanılabilecek 8 yeni bileşik sentezlendi. Benzene-1,4-diamine, 4- 4-aminofenoksi benzamine, 4- 4-aminofenoltiyo benzamine ve 4- 4-aminofenilsülfonil benzamine malononitril ile kenetlenip fenilazomalononitriller elde edildi. Etil alkol içerisinde fenilazo malononitriller bileşikleri ile hidrazinmonohidrat etkileştirilmesi ile tetraamino pirazol içeren bileşikler sentezlendi. Bileşiklerin yapıları elemental analiz, FT-IR, NMR gibi spektroskopik teknikler kullanılarak karakterize edildi. Bileşiklerin UVvis. absorpsiyon spektrumları alındı ve sonuçlar tartışıldı. Sentezlenen bileşikler 1a-d ve 2a-d boyama özelliklerinin araştırılması için polyester kumaşa uygulandı

Keywords

Diazo boyaları, poliester yapılar, malononitril, boyama özellikleri

References

• S.C. Catino, R.E. Farris., Azo dyes. In: Grayson M, editor. Concise encyclopedia chemical technology. New York: John Wiley and Sons; 1985. 142.
• K. Tanaka, K. Matsuo, A. Nakanishi, M. Jo, H. Shiota, M. Yamaguchi, S. Yoshino, K. Kawaguchi, Syntheses and antimicrobial activities of five-membered heterocycles having a phenylazo substituent, Chem Pharm Bull., 32 (1984) 3291.
• A.A. Fadda, H.A. Etmen, F.A. Amer, M. Barghout, K.H.S. Mohammed, Azo disperse dyes for synthetic fibers I: 2-methyl- and 2-phenylquinazolone derivatives. J. Chem Tech. Biotechnol., 61 (1994) 343.
• F. Karcı, İ. Şener, H. Deligöz. Synthesis, Characterization and Investigation of The Absorption Spectra of Substituted Azocallix[4]arenes. Dyes Pigments., 59 (2003) 53.
• F. Karci, İ. Şener, H. Deligöz, Azocalixarenes. 2: Synthesis, Characterization and Investigation of The Absorption Spectra of Azocalix[6]arenes Containing Chromogenic Groups. Dyes and Pigments., 62 (2004) 131.
• A.Z. El-Sonbai, A.A.M. Belal, S.I. El-Wakeel, M.A. Hussien, Stereochemistry of new nitrogen containing heterocyclic compounds.; X. Supramolecular structures and stereochemical versatility of polymeric complexes. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy., 60 (2004) 965.
• F. Karcı, N. Ertan, Hetarylazo disperse dyes derived from 3-methyl-1-(3,5-dipiperidino-s-triazinyl)-5- pyrazolone as coupling component. Dyes Pigments., 55 (2002) 99.
• G.J. Hallas. J. Soc Dyers Color., 95 (1979) 285. And Giffiths G. Rev Prog Color. 11 (1981) 37. In this article Z. Seferoglu and N. Ertan. Russian in Zhurnal Organicheskoi Khimii., 43 (2007) 1041.
• İ. Sener, F. Karcı, E. Kılıc, H. Deligöz, Azocalixarenes. 3: synthesis and investigation of the absorption spectra of hetarylazodisperse dyes derived from calix[4] arene. Dyes Pigments., 62 (2004) 141.
• A.D. Towns, Developments in azo disperse dyes derived from heterocyclic diazo components. Dyes Pigments., 42 (1999) 3.
• S. Scheibye, A.A. El-Barbary, S.O. Laweson, H. Fritz, G. Rihs, Studies on organophosphorus compounds- XLI: Formation of 3-pyrazoline-5-thione disulfides from 3,5-pyrazolidinediones. C-alkylation of 3,5-pyrazolidinediones. Tetrahedron, 38 (1982) 3753.
• A. Weissberger, R.H. Wiley, P. Wiley. editors. The chemistry of heterocylic compounds: pyrazoinones, pyrazolidones and derivatives. New York John Wiley: 1964.
• S.P. Hiremith, K. Rudresh, A.R.I. Saundan, J. Indian Chem. Soc., 41 B (2002) 394.
• S. Joerg, G. Reinhold, S. Otto, S.H. Joachim, S. Robert, L. Klaus, Ger Offen 1988, DE3, 625, 686 (CIC07D 231/22). C.A. 1988, 108, 167465.
• P.N. Dhol, T.E. Achary, A. Nayak, J. Indian Chem Soc., 52 (1975) 1196.
• F.R. Souza, V.T. Souaza, V. Ratzlaff, L.P. Borges, M.R. Oliveira, H.G. Bonacorso, N. Zanatta, M.A.P. Martins, C.F. Mello, Hypothermic and antipyretic effects of 3-methyl- and 3-phenyl-5-hydroxy-5-trichloromethyl- 4,5-dihydro-1H-pyrazole-1-carboxyamides in mice. Eur J. Pharmacol., 451 (2002) 141.
• J. Singh, R. Tripathy, PCT Int Appl. 2001. 138.
• F. Freeman, Reactions of Malononitrile Derivatives. Synthesis. 12 (1981) 925.
• Y. Tominaga, Y. Honkawa, M. Hara, A. Hosomi, Synthesis of pyrazolo[3,4-d]-pyrimidine derivatives using ketene dithioacetals. J. Heterocyclic Chem., 27 (1990) 775.
• U. Henefeld, C.W. Rees, A.J.P. White, D.G. Williams, One-pot synthesis of tetrasubstituted pyrazoles—proof of regiochemistry. Journal of the Chemical Society of Perkin Transactions I., (1996) 1545.
• S.P. Sing, D. Kumar, Reinvestigation of the reported synthesis of naphtho[2ν,1ν-4,5]-thiazolo [2,3-c] [1,2,4] triazepines. Heterocycles, 31 (1990) 855.
• L.M. Sternbach, Progress in Research 22 (1978) 229.
• N. Jaiswal, R. Jaiswal, J. Barhwal, K. Kishor, Indian J. Chem., 20 B (1981) 252.
• S.G. Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A.C. Ekinci, A. Vidin, Synthesis, characterization and pharmacological properties of some 4-arylhydrazono- 2-pyrazoline-5-one derivatives obtained from heterocyclic amines. Eur. Journal of Medicinal Chemistry., 35 (2000) 761.
• J.W. Lyga, R.M. Patera, M.J. Plummer, B.P. Halling, D.A. Yuhas, Synthesis, mechanism of action, and QSAR of herbicidal 3-substituted-2-aryl-4,5,6,7- tetrahydroindazoles. Pesticide Science., 42 (1994) 29.
• N. Ertan, Synthesis of some hetarylazopyrazolone dyes and solvent effects on their absorption spectra. Dyes and Pigments., 44 (2000) 41.
• A.K. Khalil, M.A. Hassan, M.M. Muhamed, A.M. El-Sayed, Metal salt-catalyzed diazocoupling of 3-substituted- 1H-pyrazol-2-in-5-ones in aqueous medium. Dyes and Pigments., 66 (2005) 241.
• A. Emandi, I. Serban, T. Bandula, Synthesis of some new solvatochromic 1(4)-substituted Pyrazol-5-one Azo derivatives. Dyes and Pigments, 41 (1999) 63.
• P.C. Tsai, I.J. Wang, Synthesis and solvatochromic properties of some disazo dyes derived from pyrazolo[1,5-a]pyrimidine derivatives. Dyes and Pigments., 64 (2005) 259.
• Y.W. Ho, Synthesis of some new azo pyrazolo[1,5-a] pyrimidine-thieno[2,3-b]pyridine derivatives and their application as disperse dyes. Dyes and Pigments., 64 (2005) 223.
• P.T. Chen, I.J. Wang, Synthesis and solvatochromic properties of some disazo dyes derived from pyrazolo[1,5-a]pyrimidine derivatives. Dyes and Pigments., 64 (2005) 259.
• S.M. Burkinshaw, Chemical Principles of Synthetic Fibre Dyeing. Blackie Academic Professional, London. 1995. 61.
• R.M. Christie, Colour Chemistry, RSC publication, Cambridge., 2001. 129.