Design, synthesis of new magenta dyestuffs based on thiazole azomethine disperse reactive dyes with antibacterial potential on both dyes and gamma-irradiated dyed fabric
Introduction
Traditionally, the textile fabric is used for the basic function of covering the human body. However, nowadays, there is an increasing demand for multi-functional fabrics with UV protection, anti-bacterial properties, good moisture management, flame retardant, and other comfort properties [1,2]. Consumers' demand for medical textiles and sportswear has created a large market for antibacterial and UV-protection textile products [3]. Heterocyclic azo dyes containing thiazole moiety are attractive to chemists due to their exceptional pharmacological and biological activities [[4], [5], [6], [7]], as well as their specific action against target diseases and their non-toxicity [8]. Due to the sulfur and/or nitrogen content in thiazole moiety, that are known for their excellent coloring properties, tinctorial strength, fastness, thermal stability and provide bright and strong shades ranging from red to green and blue thiazole derivatives have been widely used in the synthesis of all types of dyes, especially azo dyes [4,9]. Also, thiazoles azo dyes are of great importance because they have the advantage of bathochromic absorptions compared to the corresponding benzonide dyes and are environmentally friendly [[10], [11], [12]].
Azomethine pyrazolone dyes with magenta hues were first described by Seymour in 1934 and are commonly used in manufacture of commercial dyes such as photographic [[13], [14], [15], [16], [17], [18], [19], [20]]. Based on various literature surveys we found that a few number of researchers have attempted to apply azomethine dyes as disperse dyes for dyeing polyester fabrics [16,21]. Because of all the above, we synthesize in this research new classes of the disperse reactive azomethine dyes to investigate their efficiency upon polyester/cotton blend fabrics.
Using of blend fabrics has been developed due to the desirable economies and physical properties. In polyester–cotton blends, the fabrics provides crease recovery, dimensional stability, tensile strength, abrasion resistance and easy-care properties [[22], [23], [24], [25], [26]].
Ozone depletion has increased human exposure to ultraviolet (UV) radiation, leading to skin cancer and cataracts [27]. UV protective fabrics have received increasing attention because they provide simple and convenient protection against UV radiation [28]. In the last decade, awareness about apparel grade protective textiles, which can protect the human body from the harmful UV radiation effect of sunlight, has increased substantially [29]. In general, protection from UV radiation is obtained by applying sunscreen on the skin [30]. However, the weakest protection from UV rays is obtained next to leather garments, and their protective properties depend on the composition of the fabric, such as the type of fiber, the thickness of the fabric, GSM, textile structure, weave structure, applied dyes, and finishes [31].
Antimicrobial finishing of textiles is in excessive demand to control the growth of microorganisms. These microorganisms include bacteria, fungi, and mildew, and prevent fabric from deteriorating strength and quality, staining, odors, and health concerns caused by microorganisms [[32], [33], [34]]. Antibacterial fabrics are important in the medicinal field as well as in the different daily life aspects. It has been proven that the application of antimicrobial dyes to textiles can prevent bacterial growth [35]. It has been reported that the irradiation process can be used in different applications due to its several advantages, including energy-saving as a cold method, environmentally friendly, simple, and cost-effective. However, its application in the textile industry was limited, particularly as a disinfectant tool [36,37]. Because of these facts, and as a continuation of our research interest in designing and synthesizing new heterocyclic compounds with biological activity [[38], [39], [40], [41], [42], [43], [44], [45], [46]], Herein, we reported synthesis, characterization, dyeing properties and UPF blocking for a series of novel thiazole azomethine reactive disperse dyes containing a dichloro-s-triazinyl (DCT) reactive group with the hope that such dyes can be used in a commercial scale. Furthermore, the synthesized azomethine dyes ' antimicrobial activity against different clinical bacterial isolates was determined. A molecular docking study was carried out to determine the mechanism of action by which the tested azo compounds exerted their antimicrobial activity.
Section snippets
Materials and instrumentation
All reagents of analytical grade were purchased from Sigma- Aldrich and were used without further purification. Commercially available polyester/cotton blend fabric (70/30) were used for dyeing. All melting points were measured on a Gallenkamp melting point apparatus without corrections. The infrared spectra were recorded on a PerkinElmer FTIR 1430 spectrophotometer using the KBr disk technique. Ultraviolet–visible (UV–vis) absorption spectra were recorded on a SHIMADZU UV-3101PC
Chemistry
The synthetic strategies for synthesizing azomethine reactive disperse dyes 6a-d are shown in (Scheme 1, Scheme 2). Firstly, nitrosation of 2-amino-4-(pyridin-3yl) thiazole (1) using isoamyl nitrite giving an orange product, which upon recrystallization from methanol to give 2-amino-5-nitroso-thiazole 2 as orange crystals in a good yield (Scheme 1). This product is stable, and no significant change was observed in the sample. Further, condensation of 5-nitroso-4-(pyridin-3-yl)thiazol-2-amine (2
Conclusion
A series of some new azomethine dichloro-s-triazinyl reactive disperse dyes (6a–d) with antibacterial and UV protective properties contained a thiazole and pyrazolone moieties have been synthesized and characterized by various analytical techniques. The synthesized azomethine dyes showed brilliant color and brightness properties due to the existence of chromophores in their structures. Furthermore, their dyeing performance has been assessed in cotton/polyester fabrics. The dyed fabric showed
Author contribution statement
Seham A. Ibrahim: Synthesis and characterization of materials, Investigation, Fabrication and characterization of devices, Data curation, Formal analysis, Writing - original draft.
Hala F. Rizk: Supervision.
Dina S. Aboul-Magd: Preformed the biological part, Formal analysis, Data curation, Investigation, Writing - original draft.
Ahmed Ragab: Synthesis and characterization of materials, Investigation, Data curation, Formal analysis, Visualization, Docking study, Writing - original draft.
Declaration of competing interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
References (82)
Synthesis and dyeing performance of some novel thiazole azo disperse dyes
J Saudi Chem Soc
(2010)- et al.
Synthesis, characterization and pharmacological studies of copper complexes of flavone derivatives as potential anti-tuberculosis agents
J Photochem Photobiol B Biol
(2016) - et al.
Synthesis, spectral characterization and antimicrobial activity of some new azo dyes derived from 4, 6-dihydroxypyrimidine
J Mol Liq
(2012) - et al.
Synthesis, characterization and pharmacological evaluation of 2-aminothiazole incorporated azo dyes
J Mol Struct
(2020) - et al.
Optical characterization and all-optical switching of benzenesulfonamide azo dye
Optik
(2016) - et al.
α2-Adrenoceptors and 5-HT receptors mediate the antinociceptive effect of new pyrazolines, but not of dipyrone
Eur J Pharmacol
(2004) Historical review of the use of silver in the treatment of burns. I. Early uses
Burns
(2000)- et al.
Novel adamantane- pyrazole and hydrazone hybridized: design, synthesis, cytotoxic evaluation, SAR study and molecular docking simulation as carbonic anhydrase inhibitors
J Mol Struct
(2021) - et al.
In vitro cytotoxic activity of thiazole-indenoquinoxaline hybrids as apoptotic agents, design, synthesis, physicochemical and pharmacokinetic studies
Bioorg Chem
(2020) - et al.
An eco-friendly synthesis and biological screening of fused heterocyclic compounds containing a thiophene moiety via gewald reaction
J Heterocycl Chem 2
(2019)