The evaluation of printability and non-enzymatic NADH reduction of 4′-chlorophenylazo-2-naphthol for use as a printing pigment
Tóm tắt
The printability of 4′-chlorophenylazo-2-naphthol (CPAN) was evaluated on gloss-coated paper. The preliminary results indicated that the proposed pigment could be used in offset and oil-based ink production. The pigment and its potential reduction product, 4-chloroaniline, were then separated by a reverse phase high-pressure liquid chromatography system. The pigment was incubated with NADH at 37°C for half an hour at different pH values to investigate its possible reduction into the corresponding primary amines (ie 4-chloroaniline and 2-amino-1-naphthol). However, no reduction was observed. This finding indicates a desirable evidence for the pigment in terms of its stability against NADH (nicotinamide adenine dinucleotide), a known biochemical reducing agent in living organisms when the potential toxicity from aromatic primary amines is considered.
Tài liệu tham khảo
Maynard Jr C W, ‘Dye application, manufacture of dye intermediates and dyes’,Riegel’s Handbook of Industrial Chemistry, (ed) J A Kent, 809–61, Van Nostrand Reinhold, New York, 1983, ISBN0442201648
Clayton M, ‘Raw materials’,The Printing Ink Manual, (4th edition), (eds) R H Leach, C Armstrong, J F Brown, M J Mackenzie, L Randall and H G Smith, Chapter 4, 109–281, VNR International, Berkshire, England, 1988, ISBN 0-7476-0000-7
NPIRI Raw Materials Data Handbook. Volume 4: Pigments, 3–19, National Printing Ink Research Institute, 1983
Nam S and V Renganathan, ‘Nonenzymatic reduction of azo dyes by NADH’,Chemosphere,40, 351–7, 2000
Levine W G, ‘Metabolism of azo dyes: Implication for tetoxication and activation,Drug Metabolism Reviews,23, 253–309, 1991
Chung K T, ‘The significance of azoreduction in the mutagenesis and carcinogenesis of azo dyes’,Mutation Research,114, 269–81, 1983
Moller P and H Wallin, ‘Genotoxic hazards of azo pigments and other colourants related to 1-phenylazo-2-hydroxynaphthalene’,Mutation Research,462, 10–30, 2000
Tsuda S, N Matsusaka, H Madarame, S Ueno, N Susa, K Ishida, N Kawamura, K Sekihashi and Y F Sasaki, ‘The comet assay in eight mouse organs: Results with 24 azo compounds’,Mutation Research,465, 11–26, 2000
Sztandera L, A Garg, S Hayik, K L Bhat and C W Bock, ‘Mutagenicity of aminoazo dyes and their reductive-cleavage metabolites: A QSAR/QPAR investigation’,Dyes and Pigments,59, 117–33, 2003
Furniss B S, A J Hannaford, P W G Smith and A R Tatchell,Vogel’s Textbook of Practical Organic Chemistry, (5th edition), 948–50, Longman Scientific & Technical and John Wiley & Sons Inc, New York, 1989, ISBN 0-582-46236-3
Koch L, R F Milligan and S Zuckerman, ‘Identification of some important unsulfonated azo-2-naphthol dyes’,Ind Eng Chem Anal Ed,16, 755–6, 1944
Shan A, D Harbin and C W Jameson, ‘Analyses of two azo dyes by high-performance liquid chromatography’,J Chromatogr Sci,26, 439–42, 1988
Chen M, D Moir, F M Benoit and C Kubwabo, ‘Purification and identification of several sulphonated azo dyes using reversed phase high performance liquid chromatography’,Journal of Chromatography,825, 37–44, 1998
Zlotnick J A and F P Smith, ‘Chromatographic and electrophoretic approaches is in ink analysis’,Journal of Chromatography,733, 265–72, 1999
Perez-Urquiza M, M D Pratt and J L Beltran, ‘Determination of sulphonated dyes in water by ion-interaction high-performance liquid chromatography’,Journal of Chromatography A,871, 227–34, 2000
Seclaman E, A Sallo, F Elenes, C Craamareanu, C Wikete, S Timofei and Z Simon, ‘Hydrophobicity, protolytic equilibrium and chromatographic behaviour of some monoazoic dyes’,Dyes and Pigments,55, 69–77, 2002
Rehorek A, K Urbig, R Meurer, C Schafer, A Plum and G Braun, ‘Monitoring of azo dye degradation processes in a bioreactor by on-line high performance liquid chromatography’,Journal of Chromatography A,949, 263–8, 2002
Baiocchi C, M C Brussino, E Pramauro, A B Prevot, L Palmisano and G Marci, ‘Characterization of methyl orange and its photocatalytic degradation products by HPLC/UV-VIS diode array and atmospheric pressure ionization quadrupole ion trap mass spectrometry’,International Journal of Mass Spectrometry,214, 247–56, 2002
Pielesz A, I Baranowska, A Rybak and A Wlochowicz, ‘Detection and determination of aromatic amines as products of reductive splitting from selected azo dyes’,Ecotoxicology and Environmental Safety,53, 42–7 2002