Abstract
The light fastness of fabrics dyed with natural dyes is not satisfactory, which limits their applications in the textile industry. So far, the detailed photofading mechanism of natural dyes remains unclear. To improve the light fastness of cotton fabrics dyed with two natural dyes (sodium copper chlorophyllin and gardenia yellow), two additives ethylenediaminetetraacetic acid disodium salt (EDTA-2Na) and sodium citrate were used to treat the dyed cotton fabrics via the dipping-padding method. The performance results showed that both the two additives had good effects on inhibiting the photofading of the dyed fabrics. The photofading mechanism of the two natural dyes was also investigated. The results from 1,1-Diphenyl-2-picrylhydrazyl free radical (DPPH) scavenging assay and cyclic voltammetry tests demonstrated very limited antioxidant properties of the two dyes. Singlet oxygen and hydroxyl radical were detected in the photosensitizing process of the two dyes by electron paramagnetic resonance method. The photo-induced chemiluminescence (PICL) tests confirmed that the color changes of the dyed cotton fabrics were reduced because the reactivities of the two dyes to react with reactive oxygen species were dramatically reduced in the presence of EDTA-2Na and sodium citrate. End products generated in the photofading of the two dyes were detected by high-performance liquid chromatography-mass spectrometry (HPLC–MS). Based on the comprehensive analysis of above results, possible degradation pathways of the two dyes were proposed. The mechanism study in this research may help shed light on proposing universal solutions to the poor light fastness of most natural dyes on cotton.
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Adeel S, Naseer K, Javed S, Mahmmod S, Tang R-C, Amin N, Naz S (2018a) Microwave-assisted improvement in dyeing behavior of chemical and bio-mordanted silk fabric using safflower (carthamus tinctorius l) extract. J Nat Fibers 17:55–65. https://doi.org/10.1080/15440478.2018.1465877
Adeel S, Zia KM, Abdullah M, Rehman FU, Salman M, Zuber M (2019) Ultrasonic assisted improved extraction and dyeing of mordanted silk fabric using neem bark as source of natural colourant. Nat Prod Res 33:2060–2072. https://doi.org/10.1080/14786419.2018.1484466
Adeel S, Zuber M, Fazal Ur R, Zia KM (2018b) Microwave-assisted extraction and dyeing of chemical and bio-mordanted cotton fabric using harmal seeds as a source of natural dye. Environ Sci Pollut Res Int 25:11100–11110. https://doi.org/10.1007/s11356-018-1301-2
Ajmal M, Adeel S, Azeem M, Zuber M, Akhtar N, Iqbal N (2014) Modulation of pomegranate peel colourant characteristics for textile dyeing using high energy radiations. Ind Crops Prod 58:188–193. https://doi.org/10.1016/j.indcrop.2014.04.026
Alay E, Duran K, Korlu A (2016) A sample work on green manufacturing in textile industry. Sustain Chem Pharm 3:39–46. https://doi.org/10.1016/j.scp.2016.03.001
Allen NS (1994) Photofading and light stability of dyed and pigmented polymers. Polym Degrad Stab 44:357–374
Azeem M, Iqbal N, Mir RA, Adeel S, Batool F, Khan AA, Gul S (2019) Harnessing natural colorants from algal species for fabric dyeing: a sustainable eco-friendly approach for textile processing. J Appl Phycol 31:3941–3948. https://doi.org/10.1007/s10811-019-01848-z
Batool F, Iqbal N, Azeem M, Adeel S, Ali M (2019) Sustainable dyeing of cotton fabric using black carrot (daucus carota l.) plant residue as a source of natural colorant. Pol J Environ Stud 28:3081–3087. https://doi.org/10.15244/pjoes/93712
Becerir B (2005) A novel approach for estimating the relation between k/s value and dye uptake in reactive dyeing of cotton fabrics. Fibers Polym 6:5. https://doi.org/10.1007/BF02875646
Bechtold T, Mahmudali A, Mussak R (2007) Natural dyes for textile dyeing: a comparison of methods to assess the quality of canadian golden rod plant material. Dyes Pigm 75:287–293. https://doi.org/10.1016/j.dyepig.2006.06.004
Bhatti IA, Adeel S, Taj H (2014) Application of vat green 1 dye on gamma ray treated cellulosic fabric. Radiat Phys Chem 102:124–127. https://doi.org/10.1016/j.radphyschem.2014.04.015
Bilski P, Reszka K, Bilska M, Chignell CF (1996) Oxidation of the spin trap 5,5-dimethyl-1-pyrroline n-oxide by singlet oxygen in aqueous solution. J Am Chem Soc 118:9
Bosnjakovic A, Schlick S (2006) Spin trapping by 5,5-dimethylpyrroline-n-oxide in fenton media in the presence of nafion perfluorinated membranes: limitations and potential. J Phys Chem B 110:9
Brezová V, Barbieriková Z, Zukalová M, Dvoranová D, Kavan L (2014) Epr study of 17o-enriched titania nanopowders under uv irradiation. Catal Today 230:112–118. https://doi.org/10.1016/j.cattod.2013.11.026
Burns JM et al (2012) Methods for reactive oxygen species (ros) detection in aqueous environments. Aquat Sci 74:683–734. https://doi.org/10.1007/s00027-012-0251-x
Calogero G et al (2018) Photoelectrochemical and spectrophotometric studies on dye-sensitized solar cells (dscs) and stable modules (dscms) based on natural apocarotenoids pigments. Dyes Pigm 155:9
Coultate T, Blackburn RS (2018) Food colorants: their past, present and future. Color Technol 134:165–186. https://doi.org/10.1111/cote.12334
Crews PC (2013) The fading rates of some natural dyes. Stud Conserv 32:65–72. https://doi.org/10.1179/sic.1987.32.2.65
Cristea D, Vilarem G (2006) Improving light fastness of natural dyes on cotton yarn. Dyes Pigm 70:238–245. https://doi.org/10.1016/j.dyepig.2005.03.006
Davulcu A, Benli H, Şen Y, Bahtiyari Mİ (2014) Dyeing of cotton with thyme and pomegranate peel. Cellulose 21:4671–4680. https://doi.org/10.1007/s10570-014-0427-8
Deb D, Mallick N, Bhadoria PBS (2019) Analytical studies on carbohydrates of two cyanobacterial species for enhanced bioethanol production along with poly-β-hydroxybutyrate, c-phycocyanin, sodium copper chlorophyllin, and exopolysaccharides as co-products. J Cleaner Prod 221:695–709. https://doi.org/10.1016/j.jclepro.2019.02.254
Degani L, Gulmini M, Piccablotto G, Iacomussi P, Gastaldi D, Dal Bello F, Chiantore O (2017) Stability of natural dyes under light emitting diode lamps. J Cult Herit 26:12–21. https://doi.org/10.1016/j.culher.2017.02.002
Dong H, Wei M, Li J, Fang J, Gao L, Li X, Xu A (2016) Catalytic performance of supported g-c3n4 on mcm-41 in organic dye degradation with peroxymonosulfate. RSC Adv 6:70747–70755. https://doi.org/10.1039/c6ra15721a
Dong J, Ghiladi RA, Wang Q, Cai Y, Wei Q (2018) Protoporphyrin ix conjugated bacterial cellulose via diamide spacer arms with specific antibacterial photodynamic inactivation against escherichia coli. Cellulose 25:1673–1686. https://doi.org/10.1007/s10570-018-1697-3
Dong Y, Wang P, Gan L, Li B, Wen H (2019) Enhanced removal of aqueous cr (vi) using optimized fe complex on edta modified cotton fiber via photocatalytic reduction and adsorption hybrid functions. Cellulose 26:7383–7397. https://doi.org/10.1007/s10570-019-02598-4
Elgrishi N, Rountree KJ, McCarthy BD, Rountree ES, Eisenhart TT, Dempsey JL (2017) A practical beginner’s guide to cyclic voltammetry. J Chem Educ 95:197–206. https://doi.org/10.1021/acs.jchemed.7b00361
Floegel A, Kim D-O, Chung S-J, Koo SI, Chun OK (2011) Comparison of abts/dpph assays to measure antioxidant capacity in popular antioxidant-rich us foods. J Food Compos Anal 24:1043–1048. https://doi.org/10.1016/j.jfca.2011.01.008
Haji A, Ashraf S, Nasiriboroumand M, Lievens C (2020) Environmentally friendly surface treatment of wool fiber with plasma and chitosan for improved coloration with cochineal and safflower natural dyes. Fibers Polym 21:743–750. https://doi.org/10.1007/s12221-020-9587-3
Hortensteiner S (2006) Chlorophyll degradation during senescence. Annu Rev Plant Biol 57:55–77. https://doi.org/10.1146/annurev.arplant.57.032905.105212
Hou X, Yang R, Xu H, Yang Y (2012) Adsorption kinetic and thermodynamic studies of silk dyed with sodium copper chlorophyllin. Ind Eng Chem Res 51:8341–8347. https://doi.org/10.1021/ie300201j
Iravani S, Soofi GJ (2019) Measurement of oxidative stress using esr spectroscopy. In: Electron spin resonance spectroscopy in medicine. pp 73–81. 10.1007/978-981-13-2230-3_4
José Jara-Palacios M, Luisa Escudero-Gilete M, Miguel Hernández-Hierro J, Heredia FJ, Hernanz D (2017) Cyclic voltammetry to evaluate the antioxidant potential in winemaking by-products. Talanta 165:211–215. https://doi.org/10.1016/j.talanta.2016.12.058
Kasiri MB, Safapour S (2013) Natural dyes and antimicrobials for green treatment of textiles. Environ Chem Lett 12:1–13. https://doi.org/10.1007/s10311-013-0426-2
Koh E, Hong KH (2017) Preparation and properties of cotton fabrics finished with spent coffee extract. Cellulose 24:5225–5232. https://doi.org/10.1007/s10570-017-1466-8
Kuramoto N, Kitao T (1982) Contribution of superoxide ion to the photofading of dyes. Color Technol 98:159–162
Martínez A, Vargas R, Galano A (2010) Theoretical study on the chemical fate of adducts formed through free radical addition reactions to carotenoids. Theor Chem Acc 127:595–603. https://doi.org/10.1007/s00214-010-0753-3
Millington KR, Deledicque C, Jones MJ, Maurdev G (2008) Photo-induced chemiluminescence from fibrous polymers and proteins. Polym Degrad Stab 93:640–647. https://doi.org/10.1016/j.polymdegradstab.2008.01.006
Millington KR, Maurdev G (2009) Kinetics of photo-induced chemiluminescence decay from polymers. Polym J 41:1085–1091. https://doi.org/10.1295/polymj.PJ2009159
Millington KR, Zhang H, Jones MJ, Wang X (2010) The effect of dyes on photo-induced chemiluminescence emission from polymers. Polym Degrad Stab 95:34–42. https://doi.org/10.1016/j.polymdegradstab.2009.10.014
Mirjalili M, Nazarpoor K, Karimi L (2011) Eco-friendly dyeing of wool using natural dye from weld as co-partner with synthetic dye. J Cleaner Prod 19:1045–1051. https://doi.org/10.1016/j.jclepro.2011.02.001
Nosaka Y, Nosaka AY (2017) Generation and detection of reactive oxygen species in photocatalysis. Chem Rev 117:11302–11336. https://doi.org/10.1021/acs.chemrev.7b00161
Oakes J (2001) Photofading of textile dyes. Color Technol 31:21–28
Ozaki A, Kitano M, Yamaguchi H, Kuroda K, Endo G (2002) Genotoxicity of gardenia yellow and its components. Food Chem Toxicol 40:8
Ozturk E, Koseoglu H, Karaboyacı M, Yigit NO, Yetis U, Kitis M (2016) Minimization of water and chemical use in a cotton/polyester fabric dyeing textile mill. J Clean Prod 130:92–102. https://doi.org/10.1016/j.jclepro.2016.01.080
Pakdel E, Daoud WA, Sun L, Wang X (2015) Photostability of wool fabrics coated with pure and modified tio2 colloids. J Colloid Interface Sci 440:299–309. https://doi.org/10.1016/j.jcis.2014.10.032
Pakdel E, Daoud WA, Afrin T, Sun L, Wang X (2017) Enhanced antimicrobial coating on cotton and its impact on uv protection and physical characteristics. Cellulose 24:4003–4015. https://doi.org/10.1007/s10570-017-1374-y
Park SJ, Park YM (2010) Eco-dyeing and antimicrobial properties of chlorophyllin copper complex extracted from sasa veitchii. Fibers Polym 11:357–362. https://doi.org/10.1007/s12221-010-0357-5
Penttilä A, Boyle CR, Salin ML (1996) Active oxygen intermediates and chlorophyllin bleaching. Biochem Biophys Res Commun 226:135–139
Rather LJ, Akhter S, Padder RA, Hassan QP, Hussain M, Khan MA, Mohammad F (2017) Colorful and semi durable antioxidant finish of woolen yarn with tannin rich extract of acacia nilotica natural dye. Dyes Pigm 139:812–819. https://doi.org/10.1016/j.dyepig.2017.01.018
Rehman F, Sanbhal N, Naveed T, Farooq A, Wang Y, Wei W (2018) Antibacterial performance of tencel fabric dyed with pomegranate peel extracted via ultrasonic method. Cellulose 25:4251–4260. https://doi.org/10.1007/s10570-018-1864-6
Shahid M, Shahidul I, Mohammad F (2013) Recent advancements in natural dye applications: a review. J Clean Prod 53:310–331. https://doi.org/10.1016/j.jclepro.2013.03.031
Tang PL, Hao E, Du Z, Deng J, Hou X, Qin J (2019) Polysaccharide extraction from sugarcane leaves: Combined effects of different cellulolytic pretreatment and extraction methods. Cellulose 26:9423–9438. https://doi.org/10.1007/s10570-019-02740-2
Trachootham D, Alexandre J, Huang P (2009) Targeting cancer cells by ros-mediated mechanisms: a radical therapeutic approach? Nat Rev Drug Discov 8:579–591. https://doi.org/10.1038/nrd2803
Vankar PS (2000) Chemistry of natural dyes. Resonance 5:73–80
Wandt J, Jakes P, Granwehr J, Gasteiger HA, Eichel RA (2016) Singlet oxygen formation during the charging process of an aprotic lithium–oxygen battery. Angew Chem Int Ed 55:4
Yu L, Shao Y, Li D (2017) Direct combination of hydrogen evolution from water and methane conversion in a photocatalytic system over pt/tio2. Appl Catal B 204:216–223. https://doi.org/10.1016/j.apcatb.2016.11.039
Zhou WE et al (2016) Determination of gardenia yellow colorants in soft drink, pastry, instant noodles with ultrasound-assisted extraction by high performance liquid chromatography-electrospray ionization tandem mass spectrum. J Chromatogr A 1446:59–69. https://doi.org/10.1016/j.chroma.2016.03.051
Zia KM et al (2019) Influence of ultrasonic radiation on extraction and green dyeing of mordanted cotton using neem bark extract. J Ind Eng Chem 77:317–322. https://doi.org/10.1016/j.jiec.2019.04.054
Acknowledgments
The authors gratefully acknowledge financial support from the Guangdong Esquel Textiles Co. Ltd (No. 230701-3029999) and would like to express their gratitude to National Institute of Environmental Health Sciences for providing free downloads of WINSim Software and the manual to use the software. The 1st author also would like to acknowledge the Joint Doctoral Program between Deakin University and the Wuhan Textile University for providing the Postgraduate Research Scholarship and research platform.
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Zhao, Z., Zhang, M., Hurren, C. et al. Study on photofading of two natural dyes sodium copper chlorophyllin and gardenia yellow on cotton. Cellulose 27, 8405–8427 (2020). https://doi.org/10.1007/s10570-020-03351-y
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DOI: https://doi.org/10.1007/s10570-020-03351-y