New class of azo reactive disperse dyes based on quinazolinone moiety: synthesis, characterization, and dyeing performance on blend fabrics with ultraviolet protection

ABSTRACT


Introduction
When compared to azo dyes derived from simple aniline, dyes based on heterocyclic moiety were shown to have a higher degree of brightness and tinctorial strength (Yen et al., 2004;Manuela et al., 2005).These dyes are also employed to stain and paralyze microorganisms as

Materials and instrumentation
We purchased all analytical-grade reagents from Sigma-Aldrich.Commercial polyester materials were utilized for dyeing.On was stirred for up to 3 h while maintaining the pH at 6.9−7.0.The solid formed was filtered, washed with water and crystallized from ethanol to give compound 2.

General procedure for the synthesis of compounds 3a-d
To a cooled solution of aromatic amines (13.7 mmol) in concentrated HCl, a solution of sodium nitrite (0.9 g, 12.7 mmol) in water was added dropwise.The diazonium salt was added with constant stirring to a cooled solution of compound 2 (3.92 g, 8.5 mmol) in sodium hydroxide (15 ml (10%)).The mixture of the reaction was agitated for two hours at 0 °C, then the product was filtered, and crystallized from ethanol to obtain (3a-d). (

Electronic spectral studies
Electronic spectra of the rhodanine dyes

Colorimetric analysis
The color parameters of the dyed PET Where C1 and C2 are the concentrations of dye in the dyebath before and after dyeing, respectively.

Synthesis and characterization
The reaction of neutral solution of

Dyeing properties of the dyes on polyester fabrics Assessment of fastness properties
Blend fabrics were dyed using synthetic dyes at a concentration of 2% (owf).The resulting hues on the fabrics ranged from yellow to dark brown (Table 2).The fastness qualities of the dyes on mix were assessed, as indicated in Tables (3).All dyes revealed higher color yields due to their increased substantively to the fiber.
And a remarkable level of levelness upon washing suggested that these dyes had strong affinity and penetration into the fabric.The dyes' durability is demonstrated by their very good to excellent fastness to acid and alkaline sweat (3-4, 4-5).
Furthermore, the rubbing fastness (both wet and dry) is very good to excellent values (3-4, 4-5), as a result of the dyes' molecules diffusing into the materials sufficiently.
Every synthetic dye exhibits very good to excellent light fastness (5-6, 6).We deduced from the data that the dyes showed roughly comparable fastness property values for fabrics.The covalent binding connections between the dye and the fiber as well as the potent dye-dye interaction energy that can inhibit dye bleed could be the cause of the high ratings for fastness properties.All dyes revealed higher color yields due to their increased substantivity to the fiber.SC, staining on cotton; Alt, color change of dyed sample.

Color assessment
The synthetic dyes 3a-d were applied to blend fabrics, and the results showed that these dyes had visual shades ranging from yellow to dark brown.Furthermore, the presence of chromophores in their structures gave these dyes good depth and leveling qualities.The color coordinates show that the dyes have a good affinity for blend fabrics with a good degree of brightness, evenness, and depth of color.
On blend fabrics, the dye's lightness or chemotherapeutic and antibacterial agents (Algohary et al., 2021).Due to its ease of synthesis (Ming et al., 2023), wide range of pharmacological activity anticancer (Gatadi et al., 2020), anti-inflammatory (Abd El-Dayem et al., 2020), antimicrobial (Nasab et al., 2017), anti-ToCV activity (Yen et al., 2020), antiviral activity (Saul et al., 2020), and anti-influenza inhibition (Wang et al., 2020), and quinazolinone nucleus, which is present in several alkaloids, has drawn attention.Apart from its biological properties, the quinazolinone nucleus has been discovered to be an essential element in a wide variety of colored products (Acharyulu et al., 2008; Patel et al., 2010; Patel et al., 2002).The quinazolinone ring's weakly delocalized electron caused these dyes to show visual absorption maxima (λ max ) in the yellow to orange region.It has been shown that dyes with heterocyclic moiety, such as quinazoline, produce a broad spectrum of color shades on different fiber types with very good depth and levelness (Patel et al., 2010; Patel et al., 2011).These dyes also exhibit outstanding brightness and fastness features, such as low sublimation and high heat stability (Divyesh et al., 2010).Blend fabrics have become increasingly popular because of their advantageous economic and physical characteristics.Blends of polyester and cotton offer easy-care qualities, abrasion resistance, dimensional stability, tensile strength, and crease recovery (Jeyakodi et al., 2015; Chen et al., 2019; Guruprasad et al., 2015; Seham et al., 2021).Human exposure to ultraviolet (UV) radiation has increased due to ozone depletion, which has resulted in cataracts and skin cancer (Bernhard et al., 2020).It is crucial to shield the skin from UV radiation exposure that is too high.Because they offer easy and convenient protection against UV radiation, UV protective fabrics have drawn more attention (Vuthiganond et al., 2020).The last ten years have seen a significant development in knowledge regarding clothing-grade protective fabrics, which may shield the human body from the damaging effects of sunlight's UV rays (Youssef et al., 2014).The primary goal of the current effort was to create a number of novel reactive disperse dyes with quinazolinone moiety that included a reactive dichloro-s-triazinyl (DCT) group.This is an extension research program in our lab that is based on the synthesis of a new azo heterocyclic system.(Seham et al., 2021; Ahmed et al., 2023; El-Borai et al., 2013; Hala et al., 2017).To get a range of shades, different coupling components were selected.These reactive disperse dyes were tested for their dyeing performance on blend fibers as well as their fastness characteristics, exhaustion, and fixation studies.Additionally, the UV protection factor of the dyed fabrics was tested, and the results demonstrated that these dyes provided excellent UV protection.
Macbeth, CE 7000 A).The following CIELAB coordinates were measured: lightness (L*), chroma (C*), the degree of redness (+ve) and greenness (-ve) (a*), and the degree of yellowness (+ve) and blueness (-ve) (b*).The color strength (K/S) values were obtained according to the Kubelka-Munk equation (AATCC, 1991) (Metwally et al., The uptakes of the reactive disperse dyes by blend fabrics were measured by sampling the dye bath before and after dyeing.The rate of exhaustion of the dyestuffs on blend fabrics was measured at equilibrium at 100 °C.The exhaustion rate was assessed by taking samples from the dyebath at different times during the dyeing process.The optical density of the dye bath samples was then measured spectrophotometrically at (λ max ) of each dye using a calibration curve previously obtained using known dye concentrations in 50% aqueous DMF and the dye Exhaustion ratio was calculated using equation (1) (Cai et al., 2020): Fixation study Dye fixation (%F) (percentage of the exhausted dye that chemically bound on the fiber) was measured by refluxing the dyed samples in 50% aqueous DMF (liquor ratio 20:1) for 15 min to extract the unfixed dye (Ma et al., 2020).Repeat this procedure until the extract is clear.The concentration of the extract was then measured spectrophotometrically at ( λmax ) of each dye, and the dye fixation ratio was calculated using equation (2): %F= Equation 2 Where C3 is the concentration of extracted dye.From the dyebath.Ultraviolet protective factor (UPF), UV-A and UV-B transmission The UPF and ultraviolet radiation (UV-R) transmission through dyed sample is measured on a spectrophotometer (Labsphere UPF TesterV-2000F Fabric Analyzer).% transmission of UV-A, UV-B rays and UPF were measured as per AATCC 183-2010.Ultraviolet protective factor measures the effectiveness of textile fabrics in protecting the human skin from ultraviolet radiations.It is expressed as the ratio of the time required for the skin to show redness (erythema) with and without protection, under constant exposure to sunlight (Joseph et al., 2016).The UPF is calculated using the following equation (3) Louris et al., 2018; Mishra et al., is the minimal erythemal dose or quantity of radiant energy needed to produce the first detectable reddening of skin after 22 ± 2 hours of continuous exposure.
Scheme (1).Synthesis pathway of compound 2 The synthesized reactive azo dyes 3a-d is shown in Scheme (2).The diazonium salts of different aromatic amines coupled with compound 2 in basic medium to give the corresponding reactive azo compounds 3ad in a good yield.The structures of reactive dyes were confirmed by means of FT-IR, 1 H NMR, 13 C NMR and elemental analyses.The FT-IR spectra of reactive dyes 3a-d showed characteristic bands at 3403-3457 cm −1 and 1501-1596 cm −1 due to the NH stretching vibration and the azo group (N=N) bending vibration, respectively.additionally, a strong band at 1710-1711 cm −1 corresponding to the C=O group of the quinazolinone moiety and an absorption band at 1595-1664 cm −1 due to the C=N stretching vibration of the quinazolinone affinity of these dyes, and the presence of hydrophobic groups (C=O) in the chemical structures of the dyes clearly inhibits dye molecules from migrating back from the fiber to the washing solution bath, and a remarkable degree of levelness after washing indicated good penetration and affinity of these dyes to the fabric.Fastness to acid and alkaline perspiration could be very good to excellent (3-4, 4-5); these results indicate the stability of the dyes.Furthermore, due to adequate diffusion of dyes molecule into the fabrics, the rubbing fastness (wet and dry) is very good to excellent values (4-5).All the synthesized dyes show very good to excellent fastness to light (5-6, 6).From the results we concluded that the dyes revealed approximately similar results of fastness properties for fabrics.The high ratings of fastness properties could be referred to the covalent binding linkages between the dye and the fiber and strong dye-dye interaction energy that can prevent dye molecules from transferring to the fiber surface.

Fig. ( 2
Fig. (2): Absorption spectra of dyes 3a-d in DMF and Benzene (3×10 Fig.(3).All of the dyed fabrics' visual observations showed that the leveling qualities of each dye were excellent.Values of L* (positive denotes lightness, and negative denotes darkness).The color lightness value (L*) of dyes 3a-d varies

Fig. ( 3
Fig. (3): K/S values of dyed blend fabrics Exhaustion and fixation study Through pre-and post-dyeing dyebath sampling, the amount of dye absorbed by the fiber was determined.Equation (1) was utilized to calculate the absorbance of the diluted dye solution in ethanol-water (4:1, v/v) by measuring the dye's λ max .Comparative dyeing properties blend fabrics with recently developed dyes had somewhat higher primary fixation and exhaustion.Between 92% and 97% of the diffusion and excellent affinities between the dyes and the fabric.The degree of exhaustion and fixation value of a dye molecule are enhanced by the addition of a reactive group, like a triazine ring, which increases substantivity toward fibers (Faisal et al., 2020; Sakr et al., 2020) Table (4) and Fig.(4).

Table (
2) demonstrates that the dyes 3a-d were more sensitive to polar aprotic solvents than nonpolar solvents.All dyes displayed maximum sensitivity in DMF because of its polar and alkaline properties, which explain most solute-solvent interactions.