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Reactive modified curcumin for high-fastness nonaqueous SC-CO2 dyeing of cotton fabric

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Abstract

Modified curcumin, which has the advantages of low toxicity, high solubility, and little color change after modification, is very suitable for nonaqueous supercritical carbon dioxide cotton dyeing. However, the existing curcumin modification technology focuses on improving its solubility. Modified curcumin is directly adsorbed onto cotton fabrics, and the main interaction forces are van der Waals forces, which causes the poor fastness of modified curcumin to dyed cotton fabrics. In this study, reactive groups (hydroxyalkyls) were introduced into curcumin to enhance its fastness to cotton fabrics. The results showed that, similar to alkyl groups, hydroxyalkyl groups can enhance the color depth of dyed cotton fabrics by elevating the solubility of modified curcumin in supercritical carbon dioxide. The higher the solubility of modified curcumin in supercritical carbon dioxide was, the higher the K/S value of the dyed cotton fabric. Furthermore, the hydroxyl groups on the modified curcumin could form ether bonds with the hydroxyl groups on cotton fabrics. Therefore, the washing and rubbing fastness of hydroxyalkyl-curcumin-dyed cotton fabric was better than that of alkyl-curcumin-dyed cotton fabric.

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References

  • Abou Elmaaty T, Abd El-Aziz E (2018) Supercritical carbon dioxide as a green media in textile dyeing: a review. Text Res J 88:1184–1212

    Article  CAS  Google Scholar 

  • Banchero M (2013) Supercritical fluid dyeing of synthetic and natural textiles–a review. Color Technol 129:2–17

    Article  CAS  Google Scholar 

  • Changtam C, De Koning HP, Ibrahim H, Sajid MS, Gould MK, Suksamrarn A (2010a) Curcuminoid analogs with potent activity against trypanosoma and leishmania species. Eur J Med Chem 45:941–956

    Article  CAS  Google Scholar 

  • Changtam C, Hongmanee P, Suksamrarn A (2010b) Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. Eur J Med Chem 45:4446–4457

    Article  CAS  Google Scholar 

  • Chong CL, Li SQ, Yeung KW (1992) An objective method for the assessment of levelness of dyed materials. Color Technol 108:528–530

    CAS  Google Scholar 

  • El Ezaby M, Salem T, Zewail A, Issa R (1970) Spectral studies of some hydroxy-derivatives of anthraquinones. J Chem Soc B Phys Org. https://doi.org/10.1039/J29700001293

    Article  Google Scholar 

  • Elke B, Ernst C, Eckhard S (2010) Past, present and future of supercritical fluid dyeing technology—an overview. Color Technol 32:88–102

    Google Scholar 

  • Fan Y, Zhang YQ, Yan K, Long JJ (2019) Synthesis of a novel disperse reactive dye involving a versatile bridge group for the sustainable coloration of natural fibers in supercritical carbon dioxide. Adv Sci 6:1801368

    Article  Google Scholar 

  • Fidale LC, Ruiz N, Heinze T, Seoud OAE (2008) Cellulose swelling by aprotic and protic solvents: what are the similarities and differences. Macromol Chem Phys 209:1240–1254

    Article  CAS  Google Scholar 

  • Folkendt MM, Weisslopez BE, Chauvel JP, True NS (1985) Gas-phase proton NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate. J Phys Chem 89:3347–3352

    Article  CAS  Google Scholar 

  • Gao D, Cui H, Huang T, Yang D, Lin J (2014) Synthesis of reactive disperse dyes containing halogenated acetamide group for dyeing cotton fabric in supercritical carbon dioxide. J Supercrit Fluid 86:108–114

    Article  CAS  Google Scholar 

  • Gao D, Yang D, Cui H, Huang T, Lin J (2015) Supercritical carbon dioxide dyeing for PET and cotton fabric with synthesized dyes by a modified apparatus. ACS Sustain Chem Eng 3:668–674

    Article  CAS  Google Scholar 

  • Günay M (2009) Determination of dyeing levelness using surface irregularity function. Color Res Appl 34:285–290

    Article  Google Scholar 

  • Liu M, Zhao H, Wu J, Xiong X, Zheng L (2018) Eco-friendly curcumin-based dyes for supercritical carbon dioxide natural fabric dyeing. J Clean Prod 197:1262–1267

    Article  CAS  Google Scholar 

  • Long J et al (2012) Dyeing of cotton fabric with a reactive disperse dye in supercritical carbon dioxide. J Supercrit Fluid 69:13–20

    Article  CAS  Google Scholar 

  • Long J, Cui C, Zhang Y, Yuan G (2015) Clean fixation of dye on cotton in supercritical carbon dioxide with a heterogeneous and phase transfer catalytic reaction. Dyes Pigm 115:88–95

    Article  CAS  Google Scholar 

  • Luo XJ et al (2018) Novel sustainable synthesis of dyes for clean dyeing of wool and cotton fibres in supercritical carbon dioxide. J Clean Prod 199:1–10

    Article  CAS  Google Scholar 

  • Reddy N, Han S, Zhao Y, Yang Y (2013) Antimicrobial activity of cotton fabrics treated with curcumin. J Appl Polym Sci 127:2698–2702

    Article  CAS  Google Scholar 

  • Sasirekha V, Vanelle P, Terme T, Ramakrishnan V (2009) Preferential solvation of 1, 4- dimethoxy-2, 3-dimethyl-9, 10-anthraquinone-a spectrophotometric and fluorometric study. J Fluoresc 19:419–426

    Article  CAS  Google Scholar 

  • Tsukada M, Khan MMR, Miura T, Postle R, Sakaguchi A (2013) Mechanical performance of wool fabrics grafted with methacrylamide and 2-hydroxyethyl methacrylate by the kawabata evaluation system for fabric method. Text Res J 83:1242–1250

    Article  CAS  Google Scholar 

  • Wang B, Ruan X, Chen L, Chen J, Yang Y (2014) Heterogeneous chemical modification of cotton cellulose with vinyl sulfone dyes in non-nucleophilic organic solvents. Ind Eng Chem Res 53:15802–15810

    Article  CAS  Google Scholar 

  • Wu J, Zhao H, Wang M, Zhi W, Xiong X, Zheng L (2019) A novel natural dye derivative for natural fabric supercritical carbon dioxide dyeing technology. Fiber Polym 20:2376–2382

    Article  CAS  Google Scholar 

  • Xie M et al (2015) Nano-curcumin prepared via supercritical: improved anti-bacterial, anti- oxidant and anti-cancer efficacy. Int J Pharm 496:732–740

    Article  CAS  Google Scholar 

  • Yang DF, Kong XJ, Gao D, Cui HS, Huang TT, Lin JX (2017) Dyeing of cotton fabric with reactive disperse dye contain acyl fluoride group in supercritical carbon dioxide. Dyes Pigm 139:566–574

    Article  CAS  Google Scholar 

  • Yildiz O, Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2013) N-(hydroxymethyl) acrylamide as a multifunctional finish to cotton and a tether for grafting methacrylamide for biocidal coatings. J Appl Polym Sci 128:4405–4410

    Article  CAS  Google Scholar 

  • Yoshida Z, Takabayashi F (1968) Electronic spectra of mono-substituted anthraquinones and solvent effects. Tetrahedron 24:933–943

    Article  Google Scholar 

  • Zhan S, Li S, Zhao Q, Wang W, Wang J (2017) Measurement and correlation of curcumin solubility in supercritical carbon dioxide. J Chem Eng Data 62:1257–1263

    Article  CAS  Google Scholar 

  • Zhang YQ, Wei XC, Long JJ (2016) Ecofriendly synthesis and application of special disperse reactive dyes in waterless coloration of wool with supercritical carbon dioxide. J Clean Prod 133:746–756

    Article  CAS  Google Scholar 

  • Zhang J, Zheng HD, Zheng LJ (2018) Optimization of eco-friendly reactive dyeing of cellulose fabrics using supercritical carbon dioxide fluid with different humidity. J Nat Fiber 15:1–10

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Science Foundation of China [Grant Number 21706021 and 21606032].

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Authors and Affiliations

  1. School of Textile and Material Engineering, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Mingyue Wang, Mao Liu, Hongjuan Zhao, Xiaoqing Xiong & Laijiu Zheng

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  1. Mingyue Wang
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  2. Mao Liu
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  3. Hongjuan Zhao
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  4. Xiaoqing Xiong
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  5. Laijiu Zheng
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Correspondence to Hongjuan Zhao.

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Wang, M., Liu, M., Zhao, H. et al. Reactive modified curcumin for high-fastness nonaqueous SC-CO2 dyeing of cotton fabric. Cellulose 27, 10541–10551 (2020). https://doi.org/10.1007/s10570-020-03504-z

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