Elsevier

Dyes and Pigments

Volume 193, September 2021, 109504
Dyes and Pigments

Design, synthesis of new magenta dyestuffs based on thiazole azomethine disperse reactive dyes with antibacterial potential on both dyes and gamma-irradiated dyed fabric

https://doi.org/10.1016/j.dyepig.2021.109504Get rights and content

Highlights

  • Synthesis of some new thiazole azomethine disperse reactive dyes and applied to dyeing polyester/cotton blend fabrics.

  • The fastness properties, colorimetric analysis, exhaustion, fixation study and UV protection fiber were measured.

  • The new dyes have shades ranging from purple to dark purple colors with good depth, brightness, and leveling properties.

  • The synthesized dyes displayed good antibacterial activity against multidrug resistance bacteria using IZs, MIC, and MBC.

  • The molecular docking study showed good binding as a preferred mode between the dyes and DNA gyrase's active site (2XCT).

Abstract

A series of new magenta azomethine reactive disperse dyes were synthesized and applied into polyester/cotton blend fabrics. Various spectroscopic and analytical techniques characterized all the synthesized dyes. The obtained data and theoretical values of all the synthesized molecules were in good agreement with the proposed molecular structure. These dyes have proven their efficiency in dyeing blend fabrics, as they give satisfactory results in fastness properties, colorimetric data and exhaustion, fixation study. Moreover, the dyed fabrics were tested for ultraviolet protection factor and offered high ultraviolet protection. The advantage of synthesizing these dyes is quite facile, and scale-up is feasible, preferring industrial dyeing applications. The designed thiazole azomethine dyes exhibited broad-spectrum antibacterial agents against MDR Gram-positive and Gram-negative bacterial isolates, which will facilitate their rational usage in multiple therapeutic applications. Our findings also demonstrate the possibility of using gamma radiation for sterilization of dyed fabrics and the ability of radiation to intensify their antibacterial activities, thereby inhibiting any bacterial growth on the surface of textiles. The molecular docking study showed good binding as a preferred mode between the dyes and DNA gyrase's active site (2XCT).

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.

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