Evaluation of Dyeing Efficiency of Synthesized Benzimidazole- Derived AZO Dyes on Nylon 6, 6 Fabrics

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ISSA, A. GIWA, U. S. AMEURU This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-8181111/v1 This work is licensed under a CC BY 4.0 License Status: Under Review Version 1 posted 14 You are reading this latest preprint version Abstract This study delves into the application of synthesized benzimidazole-derived azo dyes to nylon 6, 6 fabrics and evaluation of their dyeing efficiency. As earlier reported in first series of this research, ten novel azo acid dyes were synthesized from benzimidazole derivatives using H-acid, Gamma acid, J-acid and Tobias acid as the coupling components and both the synthesized intermediates and the dyes were characterised and their properties and structures confirmed using UV-Visible, FT-IR and 1 H NMR spectroscopic techniques. The dyeing efficiency of the dyes was investigated on nylon 6, 6 fabrics, and the fastness to perspiration, light and washing were assessed. They showed very good percentage exhaustion (64 ‒ 89) % on nylon 6, 6 with bright and dark intense hues of red, blue and purple. The synthesized azo acid dyes showed very good to excellent (4 ‒ 5) fastness to perspiration, fair to very good fastness to light (3 ‒ 6) and also fair to very good fastness to washing (2 ‒ 4). azo dye dyeing fastness fabric Introduction Before the mid-nineteenth century, all dyes were obtained from plant, animal or mineral sources and were applied using mordants, which facilitate the substantivity (Waring and Hallas, 1990 : Christie, 2015 ). Synthetic dyes came to light around 1771 as a result of limitations of natural dyes such as poor fastness properties, time-consuming and labour-intensive extractions that were not suitable for commercial production, high cost of transportation of the dye from one region to another which in turn results in high cost of the dyes and difficulty in production (Waring and Hallas, 1990 ; Chatwal, 2009 ). Azo dyes constitute the largest of the most important chemical class of commercial organic colourants. In fact, one million tons per year of these dyes are produced in the world (Christie, 2015 ; Ghasemi et al., 2017 ). Also, a substantial number of acid dyes, basic dyes, reactive dyes, direct dyes, mordant dyes, disperse and ingrain dyes are azo dyes, owing to the presence of the azo chromophoric group (–N = N–) in their molecules. Aliphatic polyamides, generally known as nylons (most commonly nylon 6 and nylon 6, 6), were the first truly synthetic fibres introduced to the market primarily as replacements for silk filaments around 1940s. They can be dyed with acid dyes due to the presence of primary amino end-groups that confer substantivity for these dyes. The affinity of acid dyes for nylon is dependent on the electrostatic attraction between the negatively charged sulphonate groups in the dye and the amine end-groups on the nylon fibre, which have become positively charged through dyeing under moderately acidic conditions (Mclntyre, 2005). There is a relationship between the chemical structure of dyes and their fastness properties. Colour fastness of a material is a measure of the resistance of this material to various agencies and conditions; both dye and fibre possess required reactive groups to develop dye–fibre attachment during dyeing through chemical bonding (Broadbent, 2001 ; Chakraborty, 2010 ). Method Materials, Equipment and Procedures Materials : Ethyl acetoacetate (% purity: 98.0), o-phenylenediamine (% purity: 98.0), acetophenone (% purity: 98.0), ethyl cyanoacetate (% purity: 98.0), malononitrile (% purity: 98.0), sodium chloride (% purity: 99.0), sodium acetate (% purity: 98.0 ‒102), concentrated HCl (% purity: 98.0), ammonium acetate (% purity: 99.0), dimethyl formamide (% purity: 98.0), formic acid (% purity: 98.0), gamma acid (% purity: 98.0), caustic soda (% purity: 99.0), Tobias acid (% purity: 98.0), sodium nitrite (% purity: 99.0), ethanol (% purity: 95.0), sodium nitrite, H-acid (% purity: 98.0), and J-acid (% purity: 98.0), were all purchased from Echas Scientific Nigeria. LTD.; Haddis International; Cardinal Scientific supplies, and Royal surgical LTD, Kaduna State. Nylon 6, 6 fabric (100%) was purchased from Sabon-Gari market Zaria and was properly characterised. Equipment Gallenkamp Melting Point Apparatus (CO10127), FT-IR Spectrometer (Agilent Technologies Carry 630), Proton Nuclear Magnetic Resonance Spectrometer (Varian 400), Ultraviolet-Visible Spectrometer (Jenway 6405) and Microscal Light Fastness Tester (225). Procedures : 1. Synthesis, Purification and Characterisation of Intermediates Three intermediates − 2-[2-(1H-Benzimidazol-2-yl)-1-methyl-ethylidene]-malononitrile, 4-(1H-Benzimidazol-2-yl)-2-cyano-3-methyl-but-2-enoic acid ethyl ester and 3-(1H-Benzimidazol-2-yl)-4-phenyl-pent-3-en-2-one were synthesized from 1-(1H-benzimidazol-2-yl)-propan-2-one, purified and characterised as reported by Issa et al. (2025). 2. Synthesis, Purification and Characterisation of Intermediates Ten dyes – 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i and 1j respectively were synthesized from the three synthesized intermediates above and were purified and characterised as reported by Issa et al . (2025). 3. Dyeing Dye solutions (2% and 3%) were prepared using a fabric to liquor ratio of 1:50. For each dye, the dye was dissolved in distilled water (5 ml) with constant stirring; the pH was adjusted to 5 using glacial acetic acid (1 ml). The dye solution (50 ml) was transferred into a beaker and placed on the mantle and the temperature was allowed to rise to 60 o C after which, the semi-dried nylon fabric was immersed in the beaker while the temperature was allowed to rise to about 100 o C. This was constantly monitored using a thermometer. The dyeing was carried out for one hour. The same procedure was repeated for the other nine (9) dyes. The dyed fabrics were then removed, thoroughly washed with water and dried at room temperature. 4. Fastness Properties Determination Fastness to light The colour fastness to light was determined using microscal light fastness tester. A sample of each dyed fabric (4 x 3cm) was attached to the specimen holder of a microscal light fastness tester and the holder set in the tester. The samples were exposed to light (mercury lamp type MB/U, 400 W) for 48 h. The samples were then assessed on ‘IWS’ viewing cabinet and compared with the Blue wool light fastness reference standards, which consists of eight blue wool of different colour strength (AATCC, 2022). Fastness to washing The colour fastness to washing was determined using ISO wash fastness test number 3. Each dyed fabric (10 cm x 4 cm) was sandwiched between two adjacent fabrics and stitched. The sample and the adjacent fabrics were washed together in 100 ml beaker containing soap solution (15 cm 3 ) and sodium carbonate (10 cm 3 ) at 60 o C for 30 min, using liquor ratio of 50:1. The changes in colour of the dyed specimens were assessed after drying using the grey scale (AATCC, 2022). Fastness to perspiration Fastnesses to perspiration in acidic and alkaline solutions were determined as follows (AATCC, 2022): Fastness to perspiration in acidic solution: Each dyed sample measuring (4 × 4) cm was sandwiched between two pieces of un-dyed bleached cotton fabric measuring (4 × 4) cm. Each of the samples was thoroughly wetted in acidic solution, consisting of NaCl (5 g/l), disodium hydrogen orthophosphate dehydrate (Na 2 HPO 4 , 2.5g/l) and histidine monohydrochloride monohydrate (C 6 H 9 O 2 N 3 HCl.H 2 O, 0.5g/l) and brought to pH 5.5, with the addition of ethanoic (acetic) acid (0.1N) in a liquor ratio of 20:1 at room temperature for 30 min. After this, each of the samples was placed between two glass plates measuring about (7.5 × 6.5) cm under a load of about 4.5kg. The apparatus containing the treated fabrics was then placed in a perspirometer at (37 ± 2) °C for 4 h. The samples were finally removed from the perspirometer, dried at room temperature and changes in colour were assessed using the grey scale. Fastness to perspiration in alkaline solution: Each dyed sample measuring (4 × 4) cm was sandwiched between two pieces of un-dyed bleached cotton fabric measuring (4 × 4) cm. Each of the samples was thoroughly wetted in an alkaline solution containing NaCl (5 g/l), disodium hydrogen orthophosphate dehydrate (Na 2 HPO 4 , 2.5 g/l), histidine monohydrochloride monohydrate (C 6 H 9 O 2 N 3 HCl.H 2 O, 0.5 g/l) and the pH brought to pH 8 with the addition of sodium hydroxide (NaOH, 0.1N) in a liquor ratio of 20:1 at room temperature for 30 min. After this, each of the samples was placed between two glass plates measuring about (7.5 × 6.5) cm under a load of about 4.5kg. The apparatus containing the treated fabrics was then placed in a perspirometer at (37 ± 2) °C for 4 h. The samples were finally removed from the perspirometer, dried at room temperature and changes in colour were assessed using the grey scale. Results and Discussion Table 1 Colour Fastness Properties of the Synthesized Azo Acid Dyes on Nylon 6, 6 fabrics Dye Shade (%) Dye No. Fastness Wash Perspiration Light Change in colour Degree of staining Acid Alkaline 3 1a 3 4 5 4 1 3 1b 2 3 5 5 5 3 1c 2 3 4 4 3 3 1d 3 4 5 3 1 3 1e 2 2 4 5 6 3 1f 2 3 3 4 5 3 1g 2 3 4 4 4 3 1h 3 4 4 4 3 3 1i 3–4 4 5 4 3 3 1j 1 2 4 4 3 Table 2 Key for Fastness Rating Wash & perspiration fastness Light fastness 1. Very poor 1. Very poor 2. Fair 2. Poor 3. Good 3. Fair 4. Very good 4. Moderate 5. Excellent 5. Good 6. Very good 7. Excellent 8. Outstanding The dyed nylon fabrics showed poor to very good light fastness (Tables 1 and 2 ). Dye 1e provided the best fastness with rating 6, indicating a very good light fastness. This is followed by dye 1b and dye 1f, each with fastness rating 5. This occurred as a result of the presence of -OH group at the para position in the dye structures and this is in complete agreement with Hagan et al. ( 2022 ), who suggested that, the presence of -OH group in the para position of the dye will give minimum fading. Dyes 1a and 1d however provided the lowest fastness rating 1, which indicates very poor light fastness. This could result from the positioning of –SO 3 H group at the para position in both dyes, since the position of this group influences fading by affecting the size and shape of the aggregated dye in the nylon 6, 6 fibre (Hagan et al., 2022 ). The presence of oxygen molecules in these dyes caused lower light fastness since it increases the fading. This is in complete agreement with Batchelor et al., ( 2003 ). Dyes 1c, 1h and 1i provided moderate light fastness that is, rating 3. Dye 1g however gave fairly-good light fastness with rating 4. This could be due to the positions of –OH and SO 3 H groups in the dye (Ortho and Meta), since their positions influence fading by affecting the size and shape of the aggregated dye in the nylon 6, 6 fibres, which is in agreement with Hagan et al., ( 2022 ). Therefore, decrease in light fastness, that is fading, is caused by both ultra-violet and visible light, with the latter being the dominant factor for azo dyes. The presence of oxygen increases the fading (Batchelor et al., 2003 ). The results of wash fastness indicated that the dyes provided fair to very good fastness on nylon (Tables 1 and 2 ). Dyes 1a, 1d, 1h, and 1i gave the best fastness rating of 4, indicating very good fastness. This may be due to higher number of reactive sites on these dyes, since the greater the number of sites attached, the better the wash fastness as emphasized by Chakraborty ( 2010 ). Similarly, the fastness rating of 3 was observed with dyed samples 1b, 1c, 1f and 1g, indicating fair fastness. For 1g, lower concentration (2%) could lead to low fastness rating, since fastness grades increase linearly with the logarithm of dye concentration so that deep shades fade more slowly than pale shades. This is in complete agreement with Venkataraman ( 1971 ). However, dyed samples 1e and 1j provided fair wash fastness. This may be due to lower number of reactive sites in these dyes; although high number of sites is contained in 1j but only a few are reactive. For fastness to perspiration, the results showed that all the dyed samples exhibited good to excellent fastness to perspiration in both acidic and alkaline conditions (Tables 1 and 2 ). Thus, the sensitivity of the dyed samples is not related to pH and this is associated with stability of the dye towards degradation under either acidic or basic conditions. This is in agreement with Abdallah et al. ( 2015 ). Dye 1d however showed fair fastness rating of 3. This may be due to low number of reactive sites attached to nylon fibre, since these reactive sites promote formation of dye-fibre interaction through chemical bonding, which eventually lead to better fastness (Chakraborty, 2010 ). Conclusion The synthesized azo acid dyes were investigated for their dyeing build-up on nylon 6, 6 fabrics and they showed very good percentage exhaustion (64 ‒ 89) %. The dyes also provided bright and dark intense hues of red, blue and purple on nylon 6, 6 fabrics. The dyeing efficiency of the synthesized dyes was investigated. The synthesized azo acid dyes showed very good to excellent (4 ‒ 5) fastness to perspiration, fair to very good fastness to light (3 ‒ 6) and also fair to very good fastness to washing (2 ‒ 4). Recommendation The synthesized dyes could also be used to dye other synthetic fibres and blends. Other fastness tests such as rubbing fastness can be carried out. Declarations Funding Declaration: no funding or sponsorship Ethics, Consent to Participate, and Consent to Public declarations: not applicable Author Contribution Declaration: Issa wrote the main manuscript draft, Giwa and Ameuru vetted and made corrections. All the authors reviewed and approved the manuscript. Competing Interests Declaration: No, I declare the authors have no competing interests as defined by Discover. Declarations: Ethical approval: No human participation was involved in this research and as such, ethical approval was not obtained. Consent to participate: No human participation was involved in the research and as such, consent to participate was not obtained. Consent to publish: No human participation was involved in the research and as such, consent to publish personal information was not obtained. Data Availability Statement: All data generated or analysed during this study are included in this published article. References Abdallah AEM, Helal MHE, Elakabawy NII. Heterocyclization, Dyeing Applications and Anticancer Evaluations of Benzimidazole Derivatives: Novel Synthesis of Thiophene, Triazole and Pyrimidine Derivatives. Egypt J Chem. 2015;58(6):699–719. AbdEl-Aal RM, Koraierm AI. Synthesis, Absorption Spectra Studies and Biological Activity of some Novel Conjugated Dyes. J Chin Chem Soc. 2000;47:389–95. American Association of Textile Chemists and Colourists [AATCC]. Manual of International Test Methods and Procedures. Volume 97. USA. Research Triangle Park; 2022. Batchelor SN, Carr D, Coleman CE, Fairclough L, Jarvis A. The Photofading Mechanism of Commercial Reactive Dyes on Cotton. Dyes Pigment. 2003;59(3):268–75. Benkhaya S, M'rabet S, Harfi AE. Classifications, Properties, Recent Synthesis and Applications of Azo Dyes. Heliyon. 2020;6:1–23. Broadbent AD. Basic Principles of Textile Coloration. England: Society of Dyers and Colourists; 2001. pp. 1–10. Chakraborty JN. Fundamentals and Practices in Colouration of Textiles. 2nd ed. New Delhi: Woodhead publishing India pvt ltd; 2010. pp. 12–325. Chakraborty JN. Fundamentals and Practices in Colouration of Textiles. 2nd ed. New Delhi: Woodhead publishing India pvt ltd; 2014. pp. 11–247. Chatwal GR. Synthetic Dyes. Mumbai: Himalaya Publishing house,; 2009. p. 11. Christie RM. Colour Chemistry. United Kingdom: Royal Society of Chemistry; 2015. pp. 72–3. Ghasemi Z, Azizi S, Salehi R, Kafil HS. Synthesis of azo dyes possessing N-heterocycles and evaluation of their anticancer and antibacterial properties. Springer-Verlag GmbH. 2017;1–3. 10.1007/s00706-017-2073-y . Hagan E, Castro–Soto I, Breault M, Poulin J. The lightfastness of Early Synthetic Organic Dyes. Herit Sci. 2022;10(50):11. https://doi.org/10.1186/s40494-022-00675-9 . Issa IO, Giwa A, Ameuru US. Synthesis, Spectra Studies and Colour Assessment of Acid Dyes Derived from Benzimidazoles on Nylon 6, 6 Fabric. Journal Sci Technology Education. 2022;10(2):294–300. Mahapatra NN. Textile Dyes. New Delhi: Woodhead Publishing India Pvt Ltd; 2016. p. 1. McIntyre JE. Synthetic Fibres: Nylon, Polyester, Acrylic, Polyolefin. England: Woodhead Publishing Ltd; 2005. pp. 20–83. Venkataraman K, editor. The Chemistry of Synthetic Dyes. Volume 6. New York: Academic; 1971. pp. 1–247. Waring DR, Hallas G, editors. The Chemistry and Application of Dyes. New York and London: Plenum Press, a division of Plenum Publishing Corporation; 1990. pp. 1–360. Additional Declarations No competing interests reported. Cite Share Download PDF Status: Under Review Version 1 posted Editorial decision: Revision requested 19 Jan, 2026 Reviews received at journal 04 Jan, 2026 Reviews received at journal 04 Jan, 2026 Reviews received at journal 30 Dec, 2025 Reviews received at journal 26 Dec, 2025 Reviewers agreed at journal 26 Dec, 2025 Reviewers agreed at journal 24 Dec, 2025 Reviewers agreed at journal 24 Dec, 2025 Reviewers agreed at journal 24 Dec, 2025 Reviewers invited by journal 24 Dec, 2025 Editor invited by journal 10 Dec, 2025 Editor assigned by journal 05 Dec, 2025 Submission checks completed at journal 04 Dec, 2025 First submitted to journal 04 Dec, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-8181111","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":565365450,"identity":"02f13a89-837b-4b0d-a23c-608b0661b913","order_by":0,"name":"IBRAHIM O. 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Synthetic dyes came to light around 1771 as a result of limitations of natural dyes such as poor fastness properties, time-consuming and labour-intensive extractions that were not suitable for commercial production, high cost of transportation of the dye from one region to another which in turn results in high cost of the dyes and difficulty in production (Waring and Hallas, \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e1990\u003c/span\u003e; Chatwal, \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2009\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eAzo dyes constitute the largest of the most important chemical class of commercial organic colourants. In fact, one million tons per year of these dyes are produced in the world (Christie, \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2015\u003c/span\u003e; Ghasemi et al., \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2017\u003c/span\u003e). Also, a substantial number of acid dyes, basic dyes, reactive dyes, direct dyes, mordant dyes, disperse and ingrain dyes are azo dyes, owing to the presence of the azo chromophoric group (\u0026ndash;N\u0026thinsp;=\u0026thinsp;N\u0026ndash;) in their molecules.\u003c/p\u003e \u003cp\u003eAliphatic polyamides, generally known as nylons (most commonly nylon 6 and nylon 6, 6), were the first truly synthetic fibres introduced to the market primarily as replacements for silk filaments around 1940s. They can be dyed with acid dyes due to the presence of primary amino end-groups that confer substantivity for these dyes. The affinity of acid dyes for nylon is dependent on the electrostatic attraction between the negatively charged sulphonate groups in the dye and the amine end-groups on the nylon fibre, which have become positively charged through dyeing under moderately acidic conditions (Mclntyre, 2005).\u003c/p\u003e \u003cp\u003eThere is a relationship between the chemical structure of dyes and their fastness properties. Colour fastness of a material is a measure of the resistance of this material to various agencies and conditions; both dye and fibre possess required reactive groups to develop dye\u0026ndash;fibre attachment during dyeing through chemical bonding (Broadbent, \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e2001\u003c/span\u003e; Chakraborty, \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e2010\u003c/span\u003e).\u003c/p\u003e"},{"header":"Method","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eMaterials, Equipment and Procedures\u003c/h2\u003e \u003cp\u003e \u003cem\u003eMaterials\u003c/em\u003e: Ethyl acetoacetate (% purity: 98.0), o-phenylenediamine (% purity: 98.0), acetophenone (% purity: 98.0), ethyl cyanoacetate (% purity: 98.0), malononitrile (% purity: 98.0), sodium chloride (% purity: 99.0), sodium acetate (% purity: 98.0 ‒102), concentrated HCl (% purity: 98.0), ammonium acetate (% purity: 99.0), dimethyl formamide (% purity: 98.0), formic acid (% purity: 98.0), gamma acid (% purity: 98.0), caustic soda (% purity: 99.0), Tobias acid (% purity: 98.0), sodium nitrite (% purity: 99.0), ethanol (% purity: 95.0), sodium nitrite, H-acid (% purity: 98.0), and J-acid (% purity: 98.0), were all purchased from Echas Scientific Nigeria. LTD.; Haddis International; Cardinal Scientific supplies, and Royal surgical LTD, Kaduna State. Nylon 6, 6 fabric (100%) was purchased from Sabon-Gari market Zaria and was properly characterised.\u003c/p\u003e \u003cp\u003e \u003cstrong\u003eEquipment\u003c/strong\u003e \u003cp\u003eGallenkamp Melting Point Apparatus (CO10127), FT-IR Spectrometer (Agilent Technologies Carry 630), Proton Nuclear Magnetic Resonance Spectrometer (Varian 400), Ultraviolet-Visible Spectrometer (Jenway 6405) and Microscal Light Fastness Tester (225).\u003c/p\u003e \u003c/p\u003e \u003cp\u003e \u003cem\u003eProcedures\u003c/em\u003e:\u003c/p\u003e \u003cp\u003e1. Synthesis, Purification and Characterisation of Intermediates\u003c/p\u003e \u003cp\u003eThree intermediates \u0026minus;\u0026thinsp;2-[2-(1H-Benzimidazol-2-yl)-1-methyl-ethylidene]-malononitrile, 4-(1H-Benzimidazol-2-yl)-2-cyano-3-methyl-but-2-enoic acid ethyl ester and 3-(1H-Benzimidazol-2-yl)-4-phenyl-pent-3-en-2-one were synthesized from 1-(1H-benzimidazol-2-yl)-propan-2-one, purified and characterised as reported by Issa \u003cem\u003eet al.\u003c/em\u003e (2025).\u003c/p\u003e \u003cp\u003e2. Synthesis, Purification and Characterisation of Intermediates\u003c/p\u003e \u003cp\u003eTen dyes \u0026ndash; 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i and 1j respectively were synthesized from the three synthesized intermediates above and were purified and characterised as reported by Issa \u003cem\u003eet al\u003c/em\u003e. (2025).\u003c/p\u003e \u003cp\u003e3. Dyeing\u003c/p\u003e \u003cp\u003eDye solutions (2% and 3%) were prepared using a fabric to liquor ratio of 1:50. For each dye, the dye was dissolved in distilled water (5 ml) with constant stirring; the pH was adjusted to 5 using glacial acetic acid (1 ml). The dye solution (50 ml) was transferred into a beaker and placed on the mantle and the temperature was allowed to rise to 60 \u003csup\u003eo\u003c/sup\u003eC after which, the semi-dried nylon fabric was immersed in the beaker while the temperature was allowed to rise to about 100 \u003csup\u003eo\u003c/sup\u003eC. This was constantly monitored using a thermometer. The dyeing was carried out for one hour. The same procedure was repeated for the other nine (9) dyes. The dyed fabrics were then removed, thoroughly washed with water and dried at room temperature.\u003c/p\u003e \u003cp\u003e4. Fastness Properties Determination\u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003eFastness to light\u003c/h3\u003e\n\u003cp\u003eThe colour fastness to light was determined using microscal light fastness tester. A sample of each dyed fabric (4 x 3cm) was attached to the specimen holder of a microscal light fastness tester and the holder set in the tester. The samples were exposed to light (mercury lamp type MB/U, 400 W) for 48 h. The samples were then assessed on \u0026lsquo;IWS\u0026rsquo; viewing cabinet and compared with the Blue wool light fastness reference standards, which consists of eight blue wool of different colour strength (AATCC, 2022).\u003c/p\u003e\n\u003ch3\u003eFastness to washing\u003c/h3\u003e\n\u003cp\u003eThe colour fastness to washing was determined using ISO wash fastness test number 3. Each dyed fabric (10 cm x 4 cm) was sandwiched between two adjacent fabrics and stitched. The sample and the adjacent fabrics were washed together in 100 ml beaker containing soap solution (15 cm\u003csup\u003e3\u003c/sup\u003e) and sodium carbonate (10 cm\u003csup\u003e3\u003c/sup\u003e) at 60 \u003csup\u003eo\u003c/sup\u003eC for 30 min, using liquor ratio of 50:1. The changes in colour of the dyed specimens were assessed after drying using the grey scale (AATCC, 2022).\u003c/p\u003e\n\u003ch3\u003eFastness to perspiration\u003c/h3\u003e\n\u003cp\u003eFastnesses to perspiration in acidic and alkaline solutions were determined as follows (AATCC, 2022):\u003c/p\u003e\n\u003ch3\u003eFastness to perspiration in acidic solution:\u003c/h3\u003e\n\u003cp\u003eEach dyed sample measuring (4 \u0026times; 4) cm was sandwiched between two pieces of un-dyed bleached cotton fabric measuring (4 \u0026times; 4) cm. Each of the samples was thoroughly wetted in acidic solution, consisting of NaCl (5 g/l), disodium hydrogen orthophosphate dehydrate (Na\u003csub\u003e2\u003c/sub\u003eHPO\u003csub\u003e4\u003c/sub\u003e, 2.5g/l) and histidine monohydrochloride monohydrate (C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eHCl.H\u003csub\u003e2\u003c/sub\u003eO, 0.5g/l) and brought to pH 5.5, with the addition of ethanoic (acetic) acid (0.1N) in a liquor ratio of 20:1 at room temperature for 30 min. After this, each of the samples was placed between two glass plates measuring about (7.5 \u0026times; 6.5) cm under a load of about 4.5kg. The apparatus containing the treated fabrics was then placed in a perspirometer at (37\u0026thinsp;\u0026plusmn;\u0026thinsp;2) \u0026deg;C for 4 h. The samples were finally removed from the perspirometer, dried at room temperature and changes in colour were assessed using the grey scale.\u003c/p\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003eFastness to perspiration in alkaline solution:\u003c/h2\u003e \u003cp\u003eEach dyed sample measuring (4 \u0026times; 4) cm was sandwiched between two pieces of un-dyed bleached cotton fabric measuring (4 \u0026times; 4) cm. Each of the samples was thoroughly wetted in an alkaline solution containing NaCl (5 g/l), disodium hydrogen orthophosphate dehydrate (Na\u003csub\u003e2\u003c/sub\u003eHPO\u003csub\u003e4\u003c/sub\u003e, 2.5 g/l), histidine monohydrochloride monohydrate (C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eHCl.H\u003csub\u003e2\u003c/sub\u003eO, 0.5 g/l) and the pH brought to pH 8 with the addition of sodium hydroxide (NaOH, 0.1N) in a liquor ratio of 20:1 at room temperature for 30 min. After this, each of the samples was placed between two glass plates measuring about (7.5 \u0026times; 6.5) cm under a load of about 4.5kg. The apparatus containing the treated fabrics was then placed in a perspirometer at (37\u0026thinsp;\u0026plusmn;\u0026thinsp;2) \u0026deg;C for 4 h. The samples were finally removed from the perspirometer, dried at room temperature and changes in colour were assessed using the grey scale.\u003c/p\u003e \u003c/div\u003e"},{"header":"Results and Discussion","content":"\u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eColour Fastness Properties of the Synthesized Azo Acid Dyes on Nylon 6, 6 fabrics\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"10\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDye Shade (%)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003eDye\u003c/p\u003e \u003cp\u003eNo.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"7\" nameend=\"c10\" namest=\"c4\"\u003e \u003cp\u003eFastness\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c2\" namest=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c6\" namest=\"c5\"\u003e \u003cp\u003eWash\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"3\" nameend=\"c9\" namest=\"c7\"\u003e \u003cp\u003ePerspiration\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003eLight\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003eChange in colour\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003eDegree of\u003c/p\u003e \u003cp\u003estaining\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003eAcid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003eAlkaline\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1a\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1b\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1c\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1d\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1f\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1g\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1h\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1i\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e3\u0026ndash;4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e1j\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eKey for Fastness Rating\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"2\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eWash \u0026amp; perspiration fastness\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eLight fastness\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1. Very poor\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1. Very poor\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2. Fair\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2. Poor\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3. Good\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3. Fair\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4. Very good\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4. Moderate\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5. Excellent\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5. Good\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e6. Very good\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e7. Excellent\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e8. Outstanding\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eThe dyed nylon fabrics showed poor to very good light fastness (Tables\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). Dye 1e provided the best fastness with rating 6, indicating a very good light fastness. This is followed by dye 1b and dye 1f, each with fastness rating 5. This occurred as a result of the presence of -OH group at the para position in the dye structures and this is in complete agreement with Hagan et al. (\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2022\u003c/span\u003e), who suggested that, the presence of -OH group in the para position of the dye will give minimum fading. Dyes 1a and 1d however provided the lowest fastness rating 1, which indicates very poor light fastness. This could result from the positioning of \u0026ndash;SO\u003csub\u003e3\u003c/sub\u003eH group at the para position in both dyes, since the position of this group influences fading by affecting the size and shape of the aggregated dye in the nylon 6, 6 fibre (Hagan et al., \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). The presence of oxygen molecules in these dyes caused lower light fastness since it increases the fading. This is in complete agreement with Batchelor et al., (\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2003\u003c/span\u003e). Dyes 1c, 1h and 1i provided moderate light fastness that is, rating 3. Dye 1g however gave fairly-good light fastness with rating 4. This could be due to the positions of \u0026ndash;OH and SO\u003csub\u003e3\u003c/sub\u003eH groups in the dye (Ortho and Meta), since their positions influence fading by affecting the size and shape of the aggregated dye in the nylon 6, 6 fibres, which is in agreement with Hagan et al., (\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Therefore, decrease in light fastness, that is fading, is caused by both ultra-violet and visible light, with the latter being the dominant factor for azo dyes. The presence of oxygen increases the fading (Batchelor et al., \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2003\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eThe results of wash fastness indicated that the dyes provided fair to very good fastness on nylon (Tables\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). Dyes 1a, 1d, 1h, and 1i gave the best fastness rating of 4, indicating very good fastness. This may be due to higher number of reactive sites on these dyes, since the greater the number of sites attached, the better the wash fastness as emphasized by Chakraborty (\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e2010\u003c/span\u003e). Similarly, the fastness rating of 3 was observed with dyed samples 1b, 1c, 1f and 1g, indicating fair fastness. For 1g, lower concentration (2%) could lead to low fastness rating, since fastness grades increase linearly with the logarithm of dye concentration so that deep shades fade more slowly than pale shades. This is in complete agreement with Venkataraman (\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e1971\u003c/span\u003e). However, dyed samples 1e and 1j provided fair wash fastness. This may be due to lower number of reactive sites in these dyes; although high number of sites is contained in 1j but only a few are reactive.\u003c/p\u003e \u003cp\u003eFor fastness to perspiration, the results showed that all the dyed samples exhibited good to excellent fastness to perspiration in both acidic and alkaline conditions (Tables\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). Thus, the sensitivity of the dyed samples is not related to pH and this is associated with stability of the dye towards degradation under either acidic or basic conditions. This is in agreement with Abdallah et al. (\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2015\u003c/span\u003e). Dye 1d however showed fair fastness rating of 3. This may be due to low number of reactive sites attached to nylon fibre, since these reactive sites promote formation of dye-fibre interaction through chemical bonding, which eventually lead to better fastness (Chakraborty, \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e2010\u003c/span\u003e).\u003c/p\u003e"},{"header":"Conclusion","content":"\u003cp\u003eThe synthesized azo acid dyes were investigated for their dyeing build-up on nylon 6, 6 fabrics and they showed very good percentage exhaustion (64 ‒ 89) %. The dyes also provided bright and dark intense hues of red, blue and purple on nylon 6, 6 fabrics. The dyeing efficiency of the synthesized dyes was investigated. The synthesized azo acid dyes showed very good to excellent (4 ‒ 5) fastness to perspiration, fair to very good fastness to light (3 ‒ 6) and also fair to very good fastness to washing (2 ‒ 4).\u003c/p\u003e \u003cp\u003e \u003cb\u003eRecommendation\u003c/b\u003e \u003c/p\u003e \u003cp\u003e \u003col\u003e \u003cspan\u003e \u003cli\u003e \u003cp\u003eThe synthesized dyes could also be used to dye other synthetic fibres and blends.\u003c/p\u003e \u003c/li\u003e \u003c/span\u003e \u003cspan\u003e \u003cli\u003e \u003cp\u003eOther fastness tests such as rubbing fastness can be carried out.\u003c/p\u003e \u003c/li\u003e \u003c/span\u003e \u003c/ol\u003e \u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003eFunding Declaration: no funding or sponsorship\u003c/p\u003e\n\u003cp\u003eEthics, Consent to Participate, and Consent to Public declarations: not applicable \u0026nbsp;\u003c/p\u003e\n\u003cp\u003eAuthor Contribution Declaration: Issa wrote the main manuscript draft, Giwa and Ameuru vetted and made corrections. All the authors reviewed and approved the manuscript.\u003c/p\u003e\n\u003cp\u003eCompeting Interests Declaration: No, I declare the authors have no competing interests as defined by Discover.\u003c/p\u003e\n\u003cp\u003eDeclarations:\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eEthical approval: No human participation was involved in this research and as such, ethical approval was not obtained.\u003c/p\u003e\n\u003cp\u003eConsent to participate: No human participation was involved in the research and as such, consent to participate was not obtained.\u003c/p\u003e\n\u003cp\u003eConsent to publish: No human participation was involved in the research and as such, consent to publish personal information was not obtained.\u003c/p\u003e\n\u003cp\u003eData Availability Statement: All data generated or analysed during this study are included in this published article.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eAbdallah AEM, Helal MHE, Elakabawy NII. Heterocyclization, Dyeing Applications and Anticancer Evaluations of Benzimidazole Derivatives: Novel Synthesis of Thiophene, Triazole and Pyrimidine Derivatives. Egypt J Chem. 2015;58(6):699\u0026ndash;719.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAbdEl-Aal RM, Koraierm AI. Synthesis, Absorption Spectra Studies and Biological Activity of some Novel Conjugated Dyes. J Chin Chem Soc. 2000;47:389\u0026ndash;95.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAmerican Association of Textile Chemists and Colourists [AATCC]. Manual of International Test Methods and Procedures. Volume 97. USA. Research Triangle Park; 2022.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBatchelor SN, Carr D, Coleman CE, Fairclough L, Jarvis A. The Photofading Mechanism of Commercial Reactive Dyes on Cotton. Dyes Pigment. 2003;59(3):268\u0026ndash;75.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBenkhaya S, M'rabet S, Harfi AE. Classifications, Properties, Recent Synthesis and Applications of Azo Dyes. Heliyon. 2020;6:1\u0026ndash;23.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBroadbent AD. Basic Principles of Textile Coloration. England: Society of Dyers and Colourists; 2001. pp. 1\u0026ndash;10.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChakraborty JN. Fundamentals and Practices in Colouration of Textiles. 2nd ed. New Delhi: Woodhead publishing India pvt ltd; 2010. pp. 12\u0026ndash;325.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChakraborty JN. Fundamentals and Practices in Colouration of Textiles. 2nd ed. New Delhi: Woodhead publishing India pvt ltd; 2014. pp. 11\u0026ndash;247.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChatwal GR. Synthetic Dyes. Mumbai: Himalaya Publishing house,; 2009. p. 11.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChristie RM. Colour Chemistry. United Kingdom: Royal Society of Chemistry; 2015. pp. 72\u0026ndash;3.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eGhasemi Z, Azizi S, Salehi R, Kafil HS. Synthesis of azo dyes possessing N-heterocycles and evaluation of their anticancer and antibacterial properties. Springer-Verlag GmbH. 2017;1\u0026ndash;3. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003e10.1007/s00706-017-2073-y\u003c/span\u003e\u003cspan address=\"10.1007/s00706-017-2073-y\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eHagan E, Castro\u0026ndash;Soto I, Breault M, Poulin J. The lightfastness of Early Synthetic Organic Dyes. Herit Sci. 2022;10(50):11. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1186/s40494-022-00675-9\u003c/span\u003e\u003cspan address=\"10.1186/s40494-022-00675-9\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eIssa IO, Giwa A, Ameuru US. Synthesis, Spectra Studies and Colour Assessment of Acid Dyes Derived from Benzimidazoles on Nylon 6, 6 Fabric. Journal Sci Technology Education. 2022;10(2):294\u0026ndash;300.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eMahapatra NN. Textile Dyes. New Delhi: Woodhead Publishing India Pvt Ltd; 2016. p. 1.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eMcIntyre JE. Synthetic Fibres: Nylon, Polyester, Acrylic, Polyolefin. England: Woodhead Publishing Ltd; 2005. pp. 20\u0026ndash;83.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eVenkataraman K, editor. The Chemistry of Synthetic Dyes. Volume 6. New York: Academic; 1971. pp. 1\u0026ndash;247.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eWaring DR, Hallas G, editors. The Chemistry and Application of Dyes. New York and London: Plenum Press, a division of Plenum Publishing Corporation; 1990. pp. 1\u0026ndash;360.\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"discover-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"","sideBox":"Learn more about [Discover Chemistry](https://link.springer.com/journal/44371)","snPcode":"44371","submissionUrl":"https://submission.nature.com/new-submission/44371/3","title":"Discover Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Discover Series","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"azo dye, dyeing, fastness, fabric","lastPublishedDoi":"10.21203/rs.3.rs-8181111/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-8181111/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis study delves into the application of synthesized benzimidazole-derived azo dyes to nylon 6, 6 fabrics and evaluation of their dyeing efficiency. As earlier reported in first series of this research, ten novel azo acid dyes were synthesized from benzimidazole derivatives using H-acid, Gamma acid, J-acid and Tobias acid as the coupling components and both the synthesized intermediates and the dyes were characterised and their properties and structures confirmed using UV-Visible, FT-IR and \u003csup\u003e1\u003c/sup\u003eH NMR spectroscopic techniques. The dyeing efficiency of the dyes was investigated on nylon 6, 6 fabrics, and the fastness to perspiration, light and washing were assessed. They showed very good percentage exhaustion (64 ‒ 89) % on nylon 6, 6 with bright and dark intense hues of red, blue and purple. The synthesized azo acid dyes showed very good to excellent (4 ‒ 5) fastness to perspiration, fair to very good fastness to light (3 ‒ 6) and also fair to very good fastness to washing (2 ‒ 4).\u003c/p\u003e","manuscriptTitle":"Evaluation of Dyeing Efficiency of Synthesized Benzimidazole- Derived AZO Dyes on Nylon 6, 6 Fabrics","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-12-25 06:14:42","doi":"10.21203/rs.3.rs-8181111/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2026-01-19T09:53:02+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-01-04T17:28:34+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2026-01-04T05:58:16+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-12-30T14:12:40+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-12-26T14:16:57+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"284521992445187504941312440852370112931","date":"2025-12-26T13:55:21+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"214399986622925212998708923646302834844","date":"2025-12-25T02:34:08+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"323490845081677359386355827418380893064","date":"2025-12-24T18:26:59+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"222706443415256069540858766929376540961","date":"2025-12-24T13:28:36+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-12-24T11:15:41+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2025-12-10T09:29:35+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-12-05T06:01:30+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-12-04T21:49:49+00:00","index":"","fulltext":""},{"type":"submitted","content":"Discover Chemistry","date":"2025-12-04T21:45:34+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"discover-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"","sideBox":"Learn more about [Discover Chemistry](https://link.springer.com/journal/44371)","snPcode":"44371","submissionUrl":"https://submission.nature.com/new-submission/44371/3","title":"Discover Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Discover Series","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"40395454-6a1d-4a61-88e4-20bc9bdb1ee3","owner":[],"postedDate":"December 25th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"under-review","subjectAreas":[],"tags":[],"updatedAt":"2026-05-12T09:12:01+00:00","versionOfRecord":[],"versionCreatedAt":"2025-12-25 06:14:42","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-8181111","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-8181111","identity":"rs-8181111","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}