Overview on natural dyes and their IR-spectra – Part II: Indigo containing plant dyes
DOI:
https://doi.org/10.25367/cdatp.2024.5.p66-80Abstract
This review paper is part of a paper series reporting on natural dyestuffs and their infrared spectra (IR spectra). The current part II is related to the dye indigo (vat blue 1). Indigo is probably the most used and the most important dye. It is related to the typical clothing product – the blue jeans. In current study, the IR spectra of natural indigos from different origin are determined and compared to the IR spectrum of synthetic indigo. Further discussed materials are a powder of indigo leaves, a pigment named indigo green, the dye indigotine blue and the natural indigoid dye tyrian purple. The recorded spectra are discussed with respect to the chemical structure of the dye and with view to the presence of possible byproducts. It is possible to estimate the origin of natural indigo by infrared spectroscopic measurements of a certain plant source. The presented overview can be used as helpful tool for persons working in the field of dyeing or quality control to support and help them to identify products by IR-spectroscopic methods.
References
Cordin, M.; Bechtold, T.; Pham, T. Quantification of aniline and N-methylaniline in indigo. Scientific Reports 2021, 1, 21135. doi.org/10.1038/s41598-021-00634-7
Fernelius, W.C.; Renfrew, E.E. Indigo. Journal of Chemical Education 1983, 60, 633-634.
Wolf, L.K. Blue jeans. Chem. Eng. News 2011, 89, 44.
Miller, D. Anthropology in blue jeans. American Ethnologist 2010, 37, 415-428. DOI: doi.org/10.1111/j.1548-1425.2010.01263.x
Schweppe, H. Handbuch der Naturfarbstoffe; ecomed Verlagsgesellschaft, Landsberg, 1993.
Aspland, J.R. Vat dyes and their application. Textile Chem. Color 1992, 24, 22-24.
Cardon, D. Natural Dyes – Sources, Tradition, Technology and Science; Archetype Publication Ltd., London, 2007.
Kirby, J.; van Bommel, M.; Verhecken, A. Natural Colorants for Dyeing and Lake Pigments; Archetype Publication Ltd., London, 2014.
Uddin, M.G. Indigo Ring Dyeing of Cotton Warp Yarns for Denim Fabric. Chemical and Materials Engineering 2014, 2, 149-154. DOI: doi.org/10.13189/cme.2014.020701.
Schmidt, H. Indigo – 100 Jahre industrielle Synthese. Chemie in unserer Zeit 1997, 31, 121-128. DOI: doi.org/10.1002/ciuz.19970310304.
Willmes, A. Taschenbuch Chemische Substanzen; Verlag Harri Deutsch, Thun, 1993.
Fabara, A.N.; Fraaije, M.W. An overview of microbial indigo-forming enzymes. Applied Microbiology and Biotechnology 2020, 104, 925-933. DOI: doi.org/10.1007/s00253-019-10292-5.
Mendoza-Avila, J.; Chauhan, K.; Vazquez-Duhalt, R. Enzymatic synthesis of indigo-derivative industrial dyes. Dyes and Pigments 2020, 178, 108384. DOI: doi.org/10.1016/j.dyepig.2020.108384.
Aino, K.; Hirota, K.; Okamoto, T.; Tu, Z.; Matsuyama, H.; Yumoto, I. Microbial communities associated with indigo fermentation that thrive in anaerobic alkaline environments. Frontiers in Microbiology 2018, 9, 1-16. DOI: doi.org/10.3389/fmicb.2018.02196.
Bhushan, B.; Samanta, S.K.; Jain, R.K. Indigo production by naphthalene‐degrading bacteria. Letters in Applied Microbiology 2000, 31, 5-9. DOI: doi.org/10.1046/j.1472-765x.2000.00754.x.
Cheng, L.; Yin, S.; Chen, M.; Sun, B.; Hao, S.; Wang, C. Enhancing indigo production by over-expression of the styrene monooxygenase in Pseudomonas putida. Current Microbiology 2016, 73, 248-254. DOI: doi.org/10.1007/s00284-016-1055-3.
Teanglum, A.; Teanglum, S.; Saithong, A. Selection of indigo plant varieties and other plants that yield indigo dye. Procedia Engineering 2012, 32, 184-190. DOI: doi.org/10.1016/j.proeng.2012.01.1255.
Mongkholrattanasit, R.; Klaichoi, C.; Rungruangkitkrai, N.; Vuthiganond, N.; Nakpathom, M. Eco-Printing on cotton fabric with natural indigo dye using wild taro corms as a new thickening agent. Journal of Natural Fibers 2022, 19, 5435-5450. DOI: doi.org/10.1080/15440478.2021.1875381.
Zheng, J.; Wang, Y.; Zhang, Q.; Wang, D.; Wang, S.; Jiao, M. Study on structure and properties of natural indigo spun-dyed viscose fiber. e-Polymers 2021, 21, 327-335. DOI: doi.org/10.1515/epoly-2021-0036
Kabish, A. K., Abate, M. T., Alemar, Z. A., & Girmay, S. The Importance of Natural Indigo Dye and Its Revitalization and Ethiopian Potential for Indigo Growing. Advances in Materials Science and Engineering, 2023. DOI: doi.org/10.1155/2023/2135014.
Pattanaik, L.; Padhi, S. K.; Hariprasad, P.; Naik, S. N. Life cycle cost analysis of natural indigo dye production from Indigofera tinctoria L. plant biomass: a case study of India. Clean Technologies and Environmental Policy 2020, 22, 1639-1654. DOI: doi.org/10.1007/s10098-020-01914-y.
Lai, C.C.; Chang, C.E. A study on sustainable design for Indigo dyeing color in the visual aspect of clothing. Sustainability 2021, 13, 3686. DOI: doi.org/10.3390/su13073686.
Jordeva, S.; Kertakova, M.; Zhezhova, S.; Longurova, S.G.; Mojsov, K. Dyeing of textiles with natural dyes. Tekstilna Industrija 2020, 68, 12-21. DOI: doi: 10.5937/tekstind2004012J.
Mahltig, B. Overview on natural dyes and their IR-spectra – Part I: Plant based dyes with naphthoquinone and anthraquinone structure. Communications in Development and Assembling of Textile Products – CDATP 2024, 5, 20-37. DOI: doi.org/10.25367/cdatp.2024.5.p20-37.
Hesse, M.; Meier, H.; Zeeh, B. Spectroscopic Methods in Organic Chemistry, Georg Thieme Verlag, 2008.
Günzler, H.; Gremlich, H.-U. IR Spectroscopy, WILEY-VCH Verlag, 2002.
Mahltig, B.; Werner, C.; Müller, M.; Jérôme, R.; Stamm, M. Protein adsorption on preadsorbed polyampholytic monolayers. J. Biomater. Sci., Polym. Edition 2001, 12, 995-1010. DOI: doi.org/10.1163/156856201753252525.
Gorgulu, S.T.; Dogan, M.; Severcan, F. The characterization and differentiation of higher plants by Fourier transform infrared spectroscopy. Appl. Spectroscopy 2007, 61, 300-308. https://opg.optica.org/as/abstract.cfm?URI=as-61-3-300.
Schulz, H.; Baranska, M. Identification and quantification of valuable plant substances by IR and Raman spectroscopy. Vibrational Spectroscopy 2007, 43, 13-25. DOI: doi.org/10.1016/j.vibspec.2006.06.001.
Peets, P.; Kaupmees, K.; Vahur, S.; Leito, I. Reflectance FT-IR spectroscopy as a viable option for textile fiber identification. Heritage Science 2019, 7, 1-10. doi.org/10.1186/s40494-019-0337-z.
Mahltig B. High-Performance Fibres – A Review of Properties and IR-Spectra. Tekstilec 2021, 64, 96-118. DOI: 10.14502/Tekstilec2021.64.96-118.
Flesner, J.; Mahltig, B. Fibers from Natural Resources. Book chapter. In: Handbook of Composites from Renewable Materials, Volume 4 – Functionalization; Thakur, V.K.; Thakur, M.K.; Kessler, M.R. (Eds.), Scrivener Publishing Wiley, Hoboken, New Jersey, USA, 2017; pp. 287-310.
Borlandelli, C.M.; Mahltig, B. Leather Types and Fiber-Based Leather Alternatives-An Overview on Selected Materials, Properties, Microscopy, Electron Dispersive Spectroscopy EDS and Infrared Spectroscopy. Ann. Textile Eng. Fashion. Technol. 2022, 1, 1-10.
Goyal, S.; Dotter, M.; Diestelhorst, E.; Storck, J.L.; Ehrmann, A.; Mahltig, B. Extraction of keratin from wool and its use as biopolymer in film formation and in electrospinning for composite material processing. Journal of Engineered Fibers and Fabrics 2022, 17, 15589250221090499. DOI: doi.org/10.1177/15589250221090499.
Carl Roth GmbH (Karlsruhe, Germany), product web page for Indigo, synthetic. https://www.carlroth.com/de/de/farbstoffe/indigo-%28c-i-%C2%A073000%29/p/3903.1 (accessed 2023-01-16).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Indigo, genuine. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/36000-indigo-genuine.html (accessed 2023-01-16).
Pflanzenfärbershop (Hückelhoven-Baal, Germany), product web page for Indigo, genuine. https://shop.pflanzenfaerber.eu/farbepflanzenextrakte/318-indigopflanzen-indigo-indigofera-tinctoria-extractum-10g.html (accessed 2023-01-16).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Indigo, Japanese polygonum. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/natural-organic-dyes-vegetable-color-paints/36004-indigo-japanese-polygonum.html (accessed 2023-01-16).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Indigo from Woad. https://www.kremer-pigmente.com/en/shop/pigments/kremer-made-and-historic-pigments/36003-indigo-made-of-woad.html (accessed 2023-01-16).
Pflanzenfärbershop (Hückelhoven-Baal, Germany), product web page for Indigo from Woad. https://shop.pflanzenfaerber.eu/farbepflanzenextrakte/315-farberwaid-indigo-isatis-tinctoria-extractum-10g.html (accessed 2023-01-16).
Pflanzenfärbershop (Hückelhoven-Baal, Germany), product web page for Indigo from Dyer´s Knotweed (France). https://shop.pflanzenfaerber.eu/farbepflanzenextrakte/659-farberknoterich-indigo-polygonum-tinctorium-extractum-10g.html (accessed 2024-01-15).
Pflanzenfärbershop (Hückelhoven-Baal, Germany), product web page for Indigo, genuine / Guatemala. https://shop.pflanzenfaerber.eu/farbepflanzenextrakte/660-guatemala-indigo-indigofera-suffruticosa-extractum-10g.html (accessed 2024-01-15).
AMA Herbal Group (India), product web page for the product “Bio Indigo – NaturalDye”. https://amaherbal.com/bio-indigo/ (accessed 2024-01-15).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Indigo leaves, powder. https://www.kremer-pigmente.com/en/shop/new-products/dyes-vegetable-color-paints/36008-indigo-leaves.html (accessed 2023-01-16).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Indigo Green – precipitation of reseda and indigo. https://www.kremer-pigmente.com/en/shop/pigments/36267-indigo-green-0-63-u.html (accessed 2023-03-13).
Kremer Pigmente GmbH (Aichstetten, Germany) product web page for Indigotine Blue. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/94160-indigotine-blue.html (accessed 2024-01-15).
Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Tyrian Purple, genuine. https://www.kremer-pigmente.com/en/shop/pigments/36010-tyrian-purple-genuine.html (accessed 2023-03-13).
Solis Correa, H.; Ortiz, E.; Uc, V.H.; Barcelo Quintal, I.D.; Hernandez Avila, J.L. Indigo stability: an ab initio study, Molecular Simulation 2011, 37, 1085-1090. DOI: doi.org/10.1080/08927022.2011.578136.
Baran, A.; Fiedler, A.; Schulz, H.; Baranska, M. In situ Raman and IR spectroscopic analysis of indigo dye. Anal. Methods 2010, 2, 1372-1376. DOI: 10.1039/c0ay00311e.
Ju, Z.; Sun, J.; Liu, Y. Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies. Molecules 2019, 24, 3831. DOI: doi:10.3390/molecules24213831.
Angelini, L.G.; Tozzi, S.; Nassi o Di Nasso, N. Environmental factors affecting productivity, indican content, and indigo yield in Polygonum tinctorium Ait., a subtropical crop grown under temperate conditions. Journal of Agricultural and Food Chemistry 2004, 52, 7541-7547. DOI: doi.org/10.1021/jf040312b.
Nakai, A.; Tanaka, A.; Yoshihara, H.; Murai, K.; Watanabe, T.; Miyawaki, K. Blue LED light promotes indican accumulation and flowering in indigo plant, Polygonum tinctorium. Industrial Crops and Products 2020, 155, 112774. DOI: doi.org/10.1016/j.indcrop.2020.112774.
Iwaki, K.; Koya-Miyata, S.; Kohno, K.; Ushio, S.; Fukuda, S. Antimicrobial activity of Polygonum tinctorium Lour: extract against oral pathogenic bacteria. Journal of Natural Medicines 2006, 60, 121-125. DOI: doi.org/10.1007/s11418-005-0025-z.
Hagiyama, M.; Takeuchi, F.; Sugano, A.; Yoneshige, A.; Inoue, T.; Wada, A.; Kajiyama, H.; Takaoka, Y.; Sasaki, K.; Ito, A. Indigo plant leaf extract inhibits the binding of SARS‑CoV‑2 spike protein to angiotensin‑converting enzyme 2. Experimental and Therapeutic Medicine 2022, 23, 1-8. DOI: doi.org/10.3892/etm.2022.11200.
Trueb, L.F. Pflanzliche Naturstoffe; Gebr. Borntraeger Verlagsbuchhandlung, Stuttgart, 2015.
Clark, R.J.; Cooksey, C.J.; Daniels, M.A.; Withnall, R. Indigo, woad, and Tyrian Purple: important vat dyes from antiquity to the present. Endeavour 1993, 17, 191-199. DOI: doi.org/10.1016/0160-9327(93)90062-8.
Maugard, T.; Enaud, E.; Choisy, P.; Legoy, M.D. Identification of an indigo precursor from leaves of Isatis tinctoria (Woad). Phytochemistry 2001, 58, 897-904. DOI: doi.org/10.1016/S0031-9422(01)00335-1.
Minami, Y.; Nishimura, O.; Hara-Nishimura, I.; Nishimura, M.; Matsubara, H. Tissue and intracellular localization of indican and the purification and characterization of indican synthase from indigo plants. Plant and Cell Physiology 2000, 41, 218-225. DOI: doi.org/10.1093/pcp/41.2.218.
Song, J.; Imanaka, H.; Imamura, K.; Kajitani, K.; Nakanishi, K. Development of a highly efficient indigo dyeing method using indican with an immobilized β-glucosidase from Aspergillus niger. Journal of Bioscience and Bioengineering 2010, 110, 281-287. DOI: doi.org/10.1016/j.jbiosc.2010.03.010.
Delano-Smith, C.; Barber, P.; Bove, D.; Clarkson, C.; Harvey, P.D.; Millea, N.; Saul, N.; Shannon, W.; Whittick, C.; Willoughby, J. New light on the medieval Gough map of Britain. Imago Mundi 2017, 69, 1-36. DOI: doi.org/10.1080/03085694.2017.1242838.
Cerrato, A.; De Santis, D.; Moresi, M. Production of luteolin extracts from Reseda luteola and assessment of their dyeing properties. Journal of the Science of Food and Agriculture 2002, 82, 1189-1199. DOI: doi.org/10.1002/jsfa.1160.
Deveoglu, O.; Karadag, R. A Review on the Flavonoids – A Dye Source. Int. J. Adv. Eng. Pure Sci. 2019, 3, 188-200. DOI: 10.7240/jeps.476514.
Pagnacco, M.C.; Maksimovic, J.P.; Nikolic, N.T., Bogdanovic, D.V.B.; Kragovic, M.M.; Stojmenovic, M.D.; Blagojevic, S.N.; Sencanski, J.V. Indigo Carmine in a Food Dye: Spectroscopic Characterization and Determining Its Micro-Concentration through the Clock Reaction. Molecules 2022, 27, 1-15. DOI: doi.org/10.3390/molecules27154853.
Volkov, V.V.; Chelli, R.; Righini, R.; Perry, C.C. Indigo chromophores and pigments: Structure and dynamics. Dyes and Pigments 2020, 172, 107761. DOI: doi.org/10.1016/j.dyepig.2019.1077.
Abdelileh, M.; Ticha, M.B.; Moussa, I.; Meksi, N. Pretreatment optimization process of cotton to overcome the limits of its dyeability with indigo carmine. Chem. Ind. Chem. Eng. Q. 2019, 25, 277-288. DOI: doi.org/10.2298/CICEQ181115006A.
Abdelileh, M.; Ticha, M.B.; Kordoghli, B.; Khiari, R.; Meksi, N.; Dhaouadi, H. Dyeing of Modified Acrylic Fibers with Indigo Carmine: Modeling and Optimization of the Dyeing Process Using a Combination of RSM and ANN Methologies. Fibers and Polymers 2023, 24, 2377-2389. DOI: doi.org/10.1007/s12221-023-00243-3.
Clark, R.J.; Cooksey, C.J.; Daniels, M.A.; Withnall, R. Indigo, woad, and Tyrian Purple: important vat dyes from antiquity to the present. Endeavour 1993, 17, 191-199. DOI: doi.org/10.1016/0160-9327(93)90062-8.
Cooksey, C.J. Tyrian purple: 6, 6’-dibromoindigo and related compounds. Molecules 2001, 6, 736-769. DOI: doi.org/10.3390/60900736.
Cooksey, C. Tyrian purple: The first four thousand years. Science Progress 2013, 96, 171-186. DOI: doi.org/10.3184/003685013X13680345111425.
Parette, R.; McCrindle, R.; McMahon, K.S.; Pena-Abaurrea, M.; Reiner, E.; Chittim, B.; Riddell, N.; Voss, G.; Dorman, F.L.; Pearson, W.N. Halogenated indigo dyes: a likely source of 1, 3, 6, 8-tetrabromocarbazole and some other halogenated carbazoles in the environment. Chemosphere 2015, 127, 18-26. DOI: doi.org/10.1016/j.chemosphere.2015.01.001.
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