Sains Malaysiana 40(7)(2011): 765–770

 

Synthesis and Characterization of a New Heterocyclic Azo Pigment

(Sintesis dan Pencirian Pigmen Azo Heterosiklik Baru)

 

M. Asniza, A.M. Issam* & H.P.S. Abdul Khalil

School of Industrial Technology, Universiti Sains Malaysia, 11800 Penang, Malaysia

 

Diserahkan: 23 Oktober 2009 / Diterima: 28 September 2010

 

 

ABSTRACT

 

A new heterocyclic coupling agent has been produced from the reaction of maleic anhydride and p-aminophenol, namely N-(4-hydroxylpheneyl)maleimide. The coupling agent underwent azo coupling reaction with aromatic amine, which is p-aminophenol to produce a new heterocyclic azo pigment. The pigment was then subjected to solubility, hiding power and light fastness test. Fourier Transform Infrared Spectroscopy (FTIR), Ultraviolet/Visible (UV/Vis) Spectroscopy, and Nuclear Magnetic Resonance Spectroscopy (1H-NMR, 13C-NMR) were used to obtain the characteristics and structural features of the pigment.

 

Keywords: Aromatic amine; heterocyclic azo pigment; N-(4-hydroxylpheneyl)maleimide

 

 

ABSTRAK

 

Satu agen gandingan heterosiklik baru iaitu, N-(4-hydroxylpheneyl)maleimide telah dihasilkan melalui tindak balas antara malik anhidrida dan p-aminofenol. Agen gandingan tersebut kemudian melalui tindak balas gandingan azo dengan amina aromatik, iaitu p-aminofenol untuk menghasilkan pigmen azo heterosiklik baru. Ujian keterlarutan, keupayaan menutupi warna substrak dan ujian tahan luntur cahaya dilakukan terhadap pigmen. Spektroskopi Inframerah (FTIR), Spektroskopi Ultraungu/Nampak (UV/Vis), dan Spektroskopi Resonans Magnetik Nuklear (1H-NMR, 13C-NMR) digunakan untuk mengenalpasti struktur dan ciri-ciri pigmen.

 

Kata kunci: Amina aromatik; N-(4-hydroxylpheneyl)maleimide; pigmen azo heterosiklik

 

 

RUJUKAN

 

Abrahart, E.N. 1968. Dyes and Their Intermediate. London: Pregamon Press.

Bindu, R.L., Reghunadhan Nair, C.P. & Ninan, K.N. 2000. Phenolic Resins Bearings Maleimide Groups: Synthesis and Characterization. Journal of Applied Polymer Chemistry 38: 641-652.

Catino, S.C. & Farris, R.E. 1985. In M. Grayson (ed.) Azo Dyes: Concise Encyclopaedia of Chemical Technology. New York: John Wiley and Sons.

Christie, R.M. 2001. Color Chemistry. United Kingdom: Royal Society of Chemistry.

Fadda, A.A., Etman, H.A., Amer, F.A., Barghout, M. & Mohammed K.S. 1994. Azo Disperse Dyes for Synthetic Fibers. 1: 2-Methyl-and 2-phenylquinazolone Derivatives. Journal of Chemical Technology and Biotechnology 61: 343-349.

Hartman, H., M. Schulze, M. & Guenther, R. 1991. Nucleophilic Substitution in Arylazo Phenols - A Simple Route for Preparing Chlorosubstituted Azobenzenes. Dyes and Pigments 15: 255-262.

Kocaokutgen, H. & Gumrukcuoglu, I.E. 1995. Synthesis and Spectral Characterization of Some Novel Azo Dyes Containing Tert-butyl Groups. Turkish Journal of Chemistry 19: 219-223.

Law, K.Y., Tarnawskyj, I.W. & Lubberts, P.T. 1994. Azo Pigments and Their Intermediate: A Spectroscopic Assessment of Metal/Azo Complexes as Negative Charge Control Agents in Color Toners. Journal of Imaging Science and Technology 38: 81-85.

Lee, J.J., Lee, W.J. & Kim, J.P. 2003. Dispersant-Free Dyeing of Polyester with Temporarily Solubilized Azo Disperse Dyes from Indole Derivatives. Fibers and Polymers 4: 66-70.

Manuela, M.R.M., Ferreira, A.M.F.P., Pereira, M.M.F., Belsley, M. & Moura, J.C.V.P. 2009. The Synthesis and Characterization of Heterocyclic Azo Dyes Derived from 5-N,N-dialkylamino-2,2’-bithiophene Couplers. Dyes and pigments 83: 59-65.

Patai, S. 1978. (Part 2) The Chemistry of Diazonium and Diazo Group. Chichester: John Wiley & Sons.

Patton, T.C. 1979. (2nd ed.) Paint Flow and Pigment Dispersion; A Rheological Approach to Coating and Ink Technology. United States of America: John Wiley & Sons, Inc.

Peters, A.T. & Chisowa, E. 1993. Colour-Constitution Relationships in 2-acylamino-4-N,N-diethylaminoazobenzene Disperse Dyes. Dyes and Pigments 22: 223-238.

Rao, C.N.R. 1967. (2nd ed.) Ultra-Violet and Visible Spectroscopy: Chemical Applications. Butterworths, London.

Schwander, H.R. 1982. Heterocyclic Azo Coupling Components. Dyes and Pigments 3: 133-160.

Tanaka, K., Matsuo, K., Nakanishi, A., Jo, M., Shiota, H., Yamaguchi, M., Yoshino, S. & Kawaguchi, K. 1984. Synthesis and Antimicrobial Activities of Five-Membered Heterocycles Having a Phenylazo Substituent. Chemical and Pharmaceutical Bulletin 32: 3291-3298.

Trivedi, B.C. & Culbertson, B.M. 1982. Maleic Anhydride. New York and London: Plenum Press.

Venkataraman, K. 1970. The Chemistry of Synthetic Dyes, Vol. 3. New York: Academic Press.

Willy, H., Klaus, H., Wilker, G., Obleier, H. & Winter, R. 2004. (3rd ed.) Industrial Organic Pigment, Production, Properties Application. Weinheim: Wiley-VCH.

Yang, Y., Min, Z. & Yi, L. 2007. A Novel Addition Curable Novolac Bearing Phthalonitrile Groups: Synthesis, Characterization and Thermal Properties. Polymer Bulletin 59: 185-194.

 

*Pengarang untuk surat-menyurat; email: issam@usm.my

 

 

 

 

sebelumnya