Abstract
Reactive dye chemistry plays a crucial role in the dyeing of cotton fibers. Herein, to provide insight on the adaptability of salt-free reactive dyeing for sustainable environmental development, the effect of dye chemistry on the dyeing properties of cotton fibers in the proposed ethanol–carbon tetrachloride–water (EtOH–CCl4–H2O) ternary solvent system was investigated in detail. Twelve commonly used reactive dyes were selected as representative dyes and applied to cotton yarns based on their reactive groups, chromophores, and number of sulfonate groups. Compared with the conventional aqueous dyeing method, the studied copper phthalocyanine (CuPc) dyes and azo dyes showed enhanced dyeing performances in the EtOH–CCl4–H2O (55:40:5) mixture, except for the investigated anthraquinone dyes. Dyeing results of cotton yarns indicated that the studied CuPc dyes and azo dyes are suitable dye categories for dyeing cotton in the EtOH–CCl4–H2O mixture. This study may offer a theoretical strategy for the industrial-scale production of cotton fibers using the developed solvent-assisted dyeing technology. The organic solvents recovery will be carried out in the future study.
Similar content being viewed by others
Data availability
Data and materials will be made available on request.
References
Abou Elmaaty T, Elsisi H, Negm E, Ayad S, Sofan M (2022) Novel nano silica assisted synthesis of azo pyrazole for the sustainable dyeing and antimicrobial finishing of cotton fabrics in supercritical carbon dioxide. J Supercrit Fluid 179:105354. https://doi.org/10.1016/j.supflu.2021.105354
Acharya S, Abidi N, Rajbhandari R, Meulewaeter F (2014) Chemical cationization of cotton fabric for improved dye uptake. Cellulose 21(6):4693–4706. https://doi.org/10.1007/s10570-014-0457-2
Arivithamani N, Giri Dev VR (2017) Sustainable bulk scale cationization of cotton hosiery fabrics for salt-free reactive dyeing process. J Clean Prod 149:1188–1199. https://doi.org/10.1016/j.jclepro.2017.02.162
Bergel BF, Araujo LL, Santana RMC (2021) Effects of the addition of cotton fibers and cotton microfibers on the structure and mechanical properties of starch foams made from potato starch. Carbohydr Polymer Technol Appl 2:100167. https://doi.org/10.1016/j.carpta.2021.100167
Cai G, Xu Z, Yang M, Tang B, Wang X (2017) Functionalization of cotton fabrics through thermal reduction of graphene oxide. Appl Surf Sci 393:441–448. https://doi.org/10.1016/j.apsusc.2016.10.046
Chen WH, Ko WY, Chen YS, Cheng CY, Chan CM, Lin KJ (2010) Growth of copper phthalocyanine rods on Au plasmon electrodes through micelle disruption methods. Langmuir 26(4):2191–2195. https://doi.org/10.1021/la903455a
Chen L, Wang B, Chen J, Ruan X, Yang Y (2015a) Comprehensive study on cellulose swelling for completely recyclable nonaqueous reactive dyeing. Ind Eng Chem Res 54(9):2439–2446. https://doi.org/10.1021/ie504677z
Chen Y, Cao W, Wang K, Jiang J (2015b) Unprecedented phthalocyanines bearing eight di-butylamino peripheral substituents: synthesis, spectroscopy, and structure. Inorg Chem 54(20):9962–9967. https://doi.org/10.1021/acs.inorgchem.5b01734
Chen S, Zhang W, Wang C, Sun S (2016) A recycled foam coloring approach based on the reversible photo-isomerization of an azobenzene cationic surfactant. Green Chem 18(14):3972–3980. https://doi.org/10.1039/C6GC00711B
Dissanayake N, Thalangamaarachchige VD, Thakurathi M, Knight M, Quitevis EL, Abidi N (2019) Dissolution of cotton cellulose in 1:1 mixtures of 1-butyl-3-methylimidazolium methylphosphonate and 1-alkylimidazole co-solvents. Carbohydr Polym 221:63–72. https://doi.org/10.1016/j.carbpol.2019.05.071
Dong X, Gu Z, Hang C, Ke G, Jiang L, He J (2019) Study on the salt-free low-alkaline reactive cotton dyeing in high concentration of ethanol in volume. J Clean Prod 226:316–323. https://doi.org/10.1016/j.jclepro.2019.04.006
Fernandez Cid MV, Van Spronsen J, Van Der Kraan M, Veugelers WJT, Woerlee GF, Witkamp GJ (2005) Excellent dye fixation on cotton dyed in supercritical carbon dioxide using fluorotriazine reactive dyes. Green Chem 7(8):609–616. https://doi.org/10.1039/B503801D
Ferreira D, Pinto DCGA, Silva H, Girol AP, De Lourdes PM (2018) Salicornia ramosissima J. Woods seeds affected the normal regenerative function on carbon tetrachloride-induced liver and kidney injury. Biomed Pharmacother 107:283–291. https://doi.org/10.1016/j.biopha.2018.07.153
Fu C, Wang J, Shao J, Pu D, Chen J, Liu J (2015) A non-aqueous dyeing process of reactive dye on cotton. J Text Inst 106(2):152–161. https://doi.org/10.1080/00405000.2014.906103
Fu Z, Zhou S, Xia L, Mao Y, Zhu L, Cheng Y, Wang A, Zhang C, Xu W (2020) Juncus effusus fiber-based cellulose cigarette filter with 3D hierarchically porous structure for removal of PAHs from mainstream smoke. Carbohydr Polym 241:116308. https://doi.org/10.1016/j.carbpol.2020.116308
Haddar W, Elksibi I, Meksi N, Mhenni MF (2014) Valorization of the leaves of fennel (Foeniculum vulgare) as natural dyes fixed on modified cotton: a dyeing process optimization based on a response surface methodology. Ind Crop Prod 52:588–596. https://doi.org/10.1016/j.indcrop.2013.11.019
Han L, Ren Y, Fang K, Zhang K, Zhang Y, Wang W, Zhang Z, Xie R (2022) Short clean dyeing of two-component cotton/polyamide fabrics through adaptive adjustment of the dye solution. J Clean Prod 333:130077. https://doi.org/10.1016/j.jclepro.2021.130077
Hao L, Wang R, Fang K, Cai Y (2017) The modification of cotton substrate using chitosan for improving its dyeability towards anionic microencapsulated nano-pigment particles. Ind Crop Prod 95:348–356. https://doi.org/10.1016/j.indcrop.2016.10.043
He X, Tao R, Zhou T, Wang C, Xie K (2014) Structure and properties of cotton fabrics treated with functionalized dialdehyde chitosan. Carbohydr Polym 103:558–565. https://doi.org/10.1016/j.carbpol.2013.12.076
Hoque E, Acharya S, Shamshina J, Abidi N (2022) Review of foam applications on cotton textiles. Text Res J 58:00405175221107400. https://doi.org/10.1177/00405175221107400
Huang C, Yu H, Abdalkarim SYH, Li Y, Chen X, Yang X, Zhou Y, Zhang L (2022) A comprehensive investigation on cellulose nanocrystals with different crystal structures from cotton via an efficient route. Carbohydr Polym 276:118766. https://doi.org/10.1016/j.carbpol.2021.118766
Imran S, Hossain A, Parui S, Sengupta PS, Roy S, Guin PS (2018) Effect of electrolytes on the solubility and solution thermodynamics of 1-amino-4-hydroxy-9,10-anthraquinone, an analogue of anthracycline anticancer drugs, in aqueous ethanol media using theoretical and UV–Vis spectroscopic study. J Mol Liq 252:151–157. https://doi.org/10.1016/j.molliq.2017.12.098
Jiang H, Zhang L, Cai J, Ren J, Cui Z, Chen W (2018) Quinoidal bithiophene as disperse dye: substituent effect on dyeing performance. Dyes Pigments 151:363–371. https://doi.org/10.1016/j.dyepig.2018.01.017
Jiang H, Hu Q, Cai J, Cui Z, Zheng J, Chen W (2019) Synthesis and dyeing properties of indophenine dyes for polyester fabrics. Dyes Pigments 166:130–139. https://doi.org/10.1016/j.dyepig.2019.03.025
Kim HS, Muthukumar P, Ku KS, Son YA (2016) Synthesis and characterization of water-soluble phthalocyanine Copper(II) complex and its coloration on acrylic fibers. Fiber Polym 16(12):2552–2557. https://doi.org/10.1007/s12221-015-5381-z
Lim YJ, Kim TK, Cho KH (2001) Reactive dyeing of cotton in water-organic solvent mixture. Sen’i Gakkaishi 57(1):21–24. https://doi.org/10.2115/fiber.57.21
Lin C, Chen B, Liu Y, Chen Y, Liu M, Zhu JY (2021) Carboxylated cellulose nanocrystals with chiral nematic property from cotton by dicarboxylic acid hydrolysis. Carbohydr Polym 264:118039. https://doi.org/10.1016/j.carbpol.2021.118039
Liu L, Mu B, Li W, Yang Y (2019a) Cost-effective reactive dyeing using spent cooking oil for minimal discharge of dyes and salts. J Clean Prod 227:1023–1034. https://doi.org/10.1016/j.jclepro.2019.04.277
Liu L, Mu B, Li W, Yang Y (2019b) Semistable emulsion system based on spent cooking oil for pilot-scale reactive dyeing with minimal discharges. ACS Sustain Chem Eng 7(16):13698–13707. https://doi.org/10.1021/acssuschemeng.9b01003
Liyanapathiranage A, Peña MJ, Sharma S, Minko S (2020) Nanocellulose-based sustainable dyeing of cotton textiles with minimized water pollution. ACS Omega 5(16):9196–9203. https://doi.org/10.1021/acsomega.9b04498
Mohsin M, Sardar S (2019) Multi-criteria decision analysis for textile pad-dyeing and foam-dyeing based on cost, performance, productivity and sustainability. Cellulose 26(6):4143–4157. https://doi.org/10.1007/s10570-019-02337-9
Mu B, Liu L, Li W, Yang Y (2019a) High sorption of reactive dyes onto cotton controlled by chemical potential gradient for reduction of dyeing effluents. J Environ Manage 239:271–278. https://doi.org/10.1016/j.jenvman.2019.03.062
Mu B, Liu L, Li W, Yang Y (2019b) A water/cottonseed oil bath with controllable dye sorption for high dyeing quality and minimum discharges. J Clean Prod 236:117566. https://doi.org/10.1016/j.jclepro.2019.07.041
Nallathambi A, Venkateshwarapuram Rengaswami GD (2016) Salt-free reactive dyeing of cotton hosiery fabrics by exhaust application of cationic agent. Carbohydr Polym 152:1–11. https://doi.org/10.1016/j.carbpol.2016.06.087
Nallathambi A, Venkateshwarapuram Rengaswami GD (2017) Industrial scale salt-free reactive dyeing of cationized cotton fabric with different reactive dye chemistry. Carbohydr Polym 174:137–145. https://doi.org/10.1016/j.carbpol.2017.06.045
Pei L, Luo Y, Saleem MA, Wang J (2021) Sustainable pilot scale reactive dyeing based on silicone oil for improving dye fixation and reducing discharges. J Clean Prod 279:123831. https://doi.org/10.1016/j.jclepro.2020.123831
Penthala R, Oh H, Park SH, Lee IY, Ko EH, Son YA (2022) Synthesis of novel reactive disperse dyes comprising carbamate and cyanuric chloride groups for dyeing polyamide and cotton fabrics in supercritical carbon dioxide. Dyes Pigments 198:110003. https://doi.org/10.1016/j.dyepig.2021.110003
Shu D, Fang K, Liu X, Cai Y, Zhang X, Zhang J (2018) Cleaner coloration of cotton fabric with reactive dyes using a pad-batch-steam dyeing process. J Clean Prod 196:935–942. https://doi.org/10.1016/j.jclepro.2018.06.080
Shu D, Fang K, Liu X, Cai Y, An F, Qu G, Liang Y (2019) Cleaner pad-steam dyeing technology for cotton fabrics with excellent utilization of reactive dye. J Clean Prod 241:118370. https://doi.org/10.1016/j.jclepro.2019.118370
Song Z, Chen Y, Zhang C, Zhang J, Huo X, Gao Y, Pan A, Du Z, Zhou J, Zhao Y, Liu Z, Wang F, Zhang J (2020) RNA-seq reveals hormone-regulated synthesis of non-cellulose polysaccharides associated with fiber strength in a single-chromosomal-fragment-substituted upland cotton line. Crop J 8(2):273–286. https://doi.org/10.1016/j.cj.2019.11.003
Stana Kleinschek K, Ribitsch V (1998) Electrokinetic properties of processed cellulose fibers. Colloid Surf A 140(1):127–138. https://doi.org/10.1016/S0927-7757(97)00301-4
Sykam K, Försth M, Sas G, Restás Á, Das O (2021) Phytic acid: a bio-based flame retardant for cotton and wool fabrics. Ind Crop Prod 164:113349. https://doi.org/10.1016/j.indcrop.2021.113349
Tang P, Lockett LME, Zhang M, Sun G (2021) Modification of cotton fabrics with 2-diethylaminoethyl chloride for salt-free dyeing with anionic dyes. Cellulose 28(10):6699–6712. https://doi.org/10.1007/s10570-021-03942-3
Teng X, Ma W, Zhang S (2010) Application of tertiary amine cationic polyacrylamide with high cationic degree in salt-free dyeing of reactive dyes. Chinese J Chem Eng 18(6):1023–1028. https://doi.org/10.1016/S1004-9541(09)60163-4
Toprak T, Anis P, Kutlu E, Kara A (2018) Effect of chemical modification with 4-vinylpyridine on dyeing of cotton fabric with reactive dyestuff. Cellulose 25(11):6793–6809. https://doi.org/10.1007/s10570-018-2026-6
Vázquez MFB, Comini LR, Martini RE, Montoya SCN, Bottini S, Cabrera JL (2015) Ultrasonic-assisted extraction of anthraquinones from Heterophyllaea pustulata Hook f. (Rubiaceae) using ethanol–water mixtures. Ind Crop Prod 69:278–283. https://doi.org/10.1016/j.indcrop.2015.01.065
Wang GW, Zheng CL, Sun J (2016) Synthesis and salt-free dyeing characteristics of cationic reactive dyes containing polyetheramine segments. Color Technol 132(4):344–349. https://doi.org/10.1111/cote.12225
Wang A, Xia L, Zhou S, Guo H, Wang Y, Xu W (2020) Solvent assisted reactive dyeing of cotton with high exhaustion in the absence of salt. J Clean Prod 267:122062. https://doi.org/10.1016/j.jclepro.2020.122062
Wang S, Gao L, Hou A, Xie K, Song X (2021a) Design, synthesis of novel bisazo disperse dyes: Structure analysis and dyeing performance on PET. Dyes Pigments 196:109761. https://doi.org/10.1016/j.dyepig.2021.109761
Wang S, Sun L, Li Y, Wang H, Liu J, Zhu P, Dong C (2021b) Properties of flame-retardant cotton fabrics: Combustion behavior, thermal stability and mechanism of Si/P/N synergistic effect. Ind Crop Prod 173:114157. https://doi.org/10.1016/j.indcrop.2021.114157
Wang J, Zhang Z, Gong Z, Liang Y, Ai X, Sang Z, Guo J, Li X, Zheng J (2022) Analysis of the genetic structure and diversity of upland cotton groups in different planting areas based on SNP markers. Gene 809:146042. https://doi.org/10.1016/j.gene.2021.146042
Xia L, Wang A, Zhang C, Liu Y, Guo H, Ding C, Wang Y, Xu W (2018) Environmentally friendly dyeing of cotton in an ethanol–water mixture with excellent exhaustion. Green Chem 20(19):4473–4483. https://doi.org/10.1039/C8GC01814F
Xia L, Wang A, Wang Y, Zhang C, Wang Y, Zhou S, Fu Z, Zhao H, Ding C, Xu W (2021) Eco-friendly dyeing of raw cotton fibres in an ethanol–water mixture without scouring and bleaching pretreatments. Green Chem 23(2):796–807. https://doi.org/10.1039/D0GC02839H
Xiao H, Zhao T, Li C, Li M (2017) Eco-friendly approaches for dyeing multiple type of fabrics with cationic reactive dyes. J Clean Prod 165:1499–1507. https://doi.org/10.1016/j.jclepro.2017.07.174
Xu X, Gong J, Li Z, Li Q, Zhang J, Wang L, Huang J (2020) Mordant free dyeing and functionalization of wool fabrics with biocolorants derived from Apocynum venetum L. Bast. ACS Sustain Chem Eng 8(33):12686–12695. https://doi.org/10.1021/acssuschemeng.0c04757
Yi S, Dong Y, Li B, Ding Z, Huang X, Xue L (2012) Adsorption and fixation behaviour of CI Reactive Red 195 on cotton woven fabric in a nonionic surfactant Triton X-100 reverse micelle. Color Technol 128(4):306–314. https://doi.org/10.1111/j.1478-4408.2012.00381.x
Yu H, Wang Y, Zhong Y, Mao Z, Tan S (2014) Foam properties and application in dyeing cotton fabrics with reactive dyes. Color Technol 130(4):266–272. https://doi.org/10.1111/cote.12088
Zambrano MC, Pawlak JJ, Daystar J, Ankeny M, Venditti RA (2021) Impact of dyes and finishes on the aquatic biodegradability of cotton textile fibers and microfibers released on laundering clothes: Correlations between enzyme adsorption and activity and biodegradation rates. Mar Pollut Bull 165:112030. https://doi.org/10.1016/j.marpolbul.2021.112030
Zhang F, Chen Y, Lin H, Lu Y (2007) Synthesis of an amino-terminated hyperbranched polymer and its application in reactive dyeing on cotton as a salt-free dyeing auxiliary. Color Technol 123(6):351–357. https://doi.org/10.1111/j.1478-4408.2007.00108.x
Zhang H, Wang J, Xie K, Pei L, Hou A (2020) Synthesis of novel green reactive dyes and relationship between their structures and printing properties. Dyes Pigments 174:108079. https://doi.org/10.1016/j.dyepig.2019.108079
Zhang Z, Chattha MS, Ahmed S, Liu J, Liu A, Yang L, Lv N, Ma X, Li X, Hao F, Yang G (2021) Nitrogen reduction in high plant density cotton is feasible due to quicker biomass accumulation. Ind Crop Prod 172:114070. https://doi.org/10.1016/j.indcrop.2021.114070
Zhao J, Agaba A, Sui X, Mao Z, Xu H, Zhong Y, Zhang L, Wang B (2018) A heterogeneous binary solvent system for recyclable reactive dyeing of cotton fabrics. Cellulose 25(12):7381–7392. https://doi.org/10.1007/s10570-018-2069-8
Zhao J, Chen J, Chen Z, Zhang Y, Xia D, Wang Q (2020) Flexible cotton fabrics/PDA/BiOBr composite photocatalyst using bioinspired polydopamine as electron transfer mediators for dye degradation and Cr(VI) reduction under visible light. Colloid Surf A 593:124623. https://doi.org/10.1016/j.colsurfa.2020.124623
Acknowledgments
We thank Foundation of Science Research Program from the Hubei Provincial Department of Education (Q20221711), National Natural Science Foundation of China (U21A2095), National Natural Science Foundation of China (21905214), Local Science and Technology Development Projects Guided by the Central Government (2020ZYYD038), and Opening Project of State Key Laboratory of Silkworm Genome Biology, Ministry of Agriculture, Southwest University (sklsgb-2019KF08).
Funding
This work was supported by the Foundation of Science Research Program from the Hubei Provincial Department of Education (Q20221711), National Natural Science Foundation of China (U21A2095), National Natural Science Foundation of China (21905214), Local Science and Technology Development Projects Guided by the Central Government (2020ZYYD038), and Opening Project of State Key Laboratory of Silkworm Genome Biology, Ministry of Agriculture, Southwest University (sklsgb-2019KF08).
Author information
Authors and Affiliations
Contributions
A.W.: Methodology, Validation, Formal analysis, Investigation, Writing—original draft, Visualization. D.S.: Conceptualization, Validation, Supervision. C.Z.: Conceptualization, Data curation, Supervision, Funding acquisition. J.G.: Data curation, Visualization. Z.F: Validation, Visualization. Y.W.: Conceptualization, Methodology, Supervision. W.L.: Conceptualization, Project administration, Funding acquisition. L.X.: Conceptualization, Methodology, Supervision, Data Curation, Writing—review & editing, Supervision. W.X.: Conceptualization, Methodology, Resources, Supervision, Funding acquisition.
Corresponding authors
Ethics declarations
Competing interest
The authors declare no competing interests.
Consent for publication
All the authors gave consent for publication.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Wang, A., Sheng, D., Zhang, C. et al. Salt-free reactive dyeing of cotton fibers in a ternary solvent system with different reactive dye chemistries. Cellulose 30, 463–479 (2023). https://doi.org/10.1007/s10570-022-04916-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-022-04916-9