The Role of Aromatic Schiff Bases in the Dyes Techniques

Karema Masoude Abuamer, Abdussalam Ali Maihub, Marei Miloud El-Ajaily, Abdunnaser Mohamed Etorki, Mortaja Mohamed Abou-Krisha, Majda Albashir Almagani

Chemistry Department, Faculty of Science, Benghazi University, Benghazi, Libya.
Chemistry Department, Faculty of Science, South Valley University, Gena, Egypt.
Chemistry Department, Faculty of Science, Tripoli University, Tripoli, Libya.

DOI: 10.4236/ijoc.2014.41002                

Abstract

Anil compounds are Schiff bases derived from aniline moiety containing phenyl or substituted phenyl group, which sometimes called Azo dyes. These Schiff bases can be directly prepared from aromatic amine with aromatic carbonyl groups, which are stable and can be manipulated under different and suitable conditions. The phenomena of coordination of Schiff bases with metal ions give the Schiff bases the good advantages to be introduced in the dyes synthesis. The classification of dyes is based on the chemical structure or on the basis of the chromophoric system. The metal complex dyes are combinations of dyestuff and metal ions, in which the coordination complex can be applied or used to be improvement factors in dye techniques. The investigation and the characterization of the resulted dyes were performed by using different physical techniques. The produced dyes were applied to different fibres, such as sheep wool and goat hair with two Schiff bases synthesised from salicylaldehyde either with 2-aminophenol or 2-aminobenzyl alcohol. Also the investigation includes the effect of mordant type on the dyeing process.

Keywords

Dyes; 2-Aminophenol; 2-Aminobenzyl Alcohol; Salicylaldehyde; Schiff Bases; Complexation

1. Introduction

1.1. Background of the Schiff Bases chemistry

In spite of the fact that salicylaldehyde and substituted benzaldehyde compounds can react with substituted phenol, such as 2-aminophenol or 2-aminobenzyl alcohol to form Schiff base which can be introduced to the transition metal ions as coordination chemistry application. The formation of azomethine group and a large number of Schiff bases and their complexes, which have received considerable attention, and became an important subject in the areas of coordination chemistry, biology and pharmaceutical science, were synthesized and investigated. Most of substituted benzene and aromatic moiety were investigated to be antibacterial and anticancer agents. [1] -[3] .

Numerous Schiff bases and complexes have been synthesized and studied for the interesting and important properties, such as biological activity, catalytic activity in hydrogenation of olefins, transfer of an amino group, photochromic properties and complexation ability towards some toxic metals. Most chemists and scientific researchers and authors have studied most of the applications in a matter of biological properties of the Schiff base and their metal complexes to guarantee the best to use. For example, the Cu(II) complexes with two Schiff bases derived from 4-aminoantipyrine and salicylaldehyde or 2-thiophencarboxaldehyde as well as 5-methyl-2-thiophencarboxaldehyde, were found to be active against the strains of Staphylococcus aureus and Escherichia coli. The Schiff base, obtained from 2-thiophenecarboxaldehyde and 2-aminobenzoic acid and its metal complexes, shows antibacterial activity. N-Salicylideneanthranilic acid possesses antiulcer activity and the complexation with copper shows an increase in such activity [4] -[10] .

Many transition metal complexes from this kind of Schiff bases have been synthesized, such as, Aluminum (III), Iron(III), Cobalt(II), Nickel(II) and Copper(II) complexes etc. These metal ions and others have been used as mordent in dyeing techniques. The principle of complexation and mordent has the same idea in coordination applications. The reaction of salicylaldehyde with anthranilic acid or o-aminophenol has been synthesized and investigated to justify the sites of coordination. This manor shows the engagement of the hydroxyl, amino and azomethine groups in the reaction [11] , [12] .

The aim of our present study is to synthesize and to introduce the Schiff base which engaged in the complexation to see the usefulness in dyeing techniques, in which the phenolic and benzylic hydroxyl groups involve these reactions. Metal complexes with a newly prepared Schiff base derived from salicylaldehyde (or salicylaldehyde derivatives) and 2-aminophenol or 2-aminobenzyl alcohol are the subjects of the comparison. The chemical structures of the Schiff bases were proposed in Figure 1. Different physiochemical techniques were used for the identification and study of the properties of such compounds. The most important factors account for being the planar chemical conformation which justifies the color and hard/soft properties of the sites of the reaction of Schiff bases [13] , [14] .

Despite their overall structural similarity, the type of the engagement of the hydroxyl groups and the metal ions in bonding facilitate the action that is required for the purpose of staining or dyeing. The directionality in the coordination justifies the sites, the parts and the groups that can be worked in bonding. The best sites of coordination in this manor are the hydroxyl groups rather than the azomethine group, as long as these groups in appropriate positions. The difference in the location and properties of the hydroxyl groups might give this Schiff bases advantages to be remarkable good agents for the assigned purposes. As the difference of hydroxyl groups work in certain fields, such as biological activities, they work in other fields. The analytical methods of characterization such as CHN percentage compositions of the Schiff bases and complexes were determined by using microchemical analytical methods on Perkin Elmer-240C (USA) elemental analyzer. Infrared spectra of this ligand was carried out by using KBr in the range (4000 - 400 cm⁻¹) on Perkin Elmer Infrared model-337 [15] , [16] .

1.2. Background of the Synthetic Dyes

The first recorded synthetic dye was picric acid, which was produced in the 1770’s from the interaction of in-

Figure 1. Chemical structures of the Schiff bases.

Conflicts of Interest

The authors declare no conflicts of interest.

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