Overview on natural dyes and their IR-spectra – Part I: Plant based dyes with naphthoquinone and anthraquinone structure

Boris Mahltig

doi:10.25367/cdatp.2024.5.p20-37

Authors

Boris Mahltig Hochschule Niederrhein, Mönchengladbach, Germany https://orcid.org/0000-0002-2240-5581

DOI:

https://doi.org/10.25367/cdatp.2024.5.p20-37

Abstract

This is the first paper of a series of review articles reporting on natural dyes, their origin and infrared spectra (IR spectra). One aim of this review series is to compare IR spectra of natural dyes from different origin and discuss if this spectroscopic method can be used as versatile tool for the identification of natural dyes and their origin. This part I of the review series is related to four natural dyes based on the chemical structures of naphthoquinone and anthraquinone. Especially discussed are Lawson, juglone and alizarin, which are related to the natural products henna, walnut hull and madder root. Also, the natural dye based on alkanna root is investigated. Compared are the IR spectra of these natural dyes gained from different suppliers with the IR spectra of the pure chemical substances related to the natural dyes. A discussion with spectra from literature is supported. The aim of this review paper is to support infrared spectroscopic data of natural materials (natural dyes) to enable further material identification and also quality control supporting people working in the fields of fiber analytics or with production processes using natural dyes

References

Schweppe, H. Handbuch der Naturfarbstoffe; ecomed Verlagsgesellschaft, Landsberg, 1993.

Agarwal, B.J.; Patel, B.H. The reincarnation of natural colourants – A review. Chemical Weekly-Bombay 2000, 45, 139-148.

Patel, B.H. Natural dyes. Book chapter. In: Handbook of textile and industrial dyeing – Volume 1: Principles, processes and types of dyes; Clark, M. (Editor), Woodhead Publishing, Cambridge, 2011; pp. 395-424. DOI: doi.org/10.1533/9780857093974.2.395

Wardman, R.H. An Introduction to Textile Coloration; John Wiley & Sons Ltd., Hoboken, 2018.

Klöckl, I. Chemie der Farbmittel; Walter de Gruyter GmbH, Berlin, 2015.

Mahltig, B., Rabe, M., Muth, M. Textiles, Dyeing, and Finishing. Kirk-Othmer Encyclopedia of Chemical Technology 2019, 1-35. DOI: doi.org/10.1002/0471238961.0609140903011201.a01.pub2.

Fröse, A.; Schmidtke, K.; Sukmann, T.; Junger, I. J.; Ehrmann, A. Application of natural dyes on diverse textile materials. Optik 2019, 181, 215-219. DOI: doi.org/10.1016/j.ijleo.2018.12.099.

Lambert, E.; Kendall, T. The complete guide to natural dyeing; Search Press Ltd., Wellwood, 2010.

Berger, D. Färben mit Pflanzen; ökobuch Verlag GmbH, Rastede, 2021.

Fischer, D. Naturfarben auf Wolle und Seide; Books on Demand GmbH, Norderstedt, 2006.

Prinz, E. Färberpflanzen; Schweizerbart Science Publishers, Stuttgart, 2014.

Güzel, E.T.; Karadag, R. Sustainability of Organic Cotton Fabric Dyeing with a Natural Dye (Gallnut) and Analysis by Multi-technique Approach. Journal of Natural Fibers 2021, 18, 1107-1118. DOI: doi.org/10.1080/15440478.2019.1687064

Karadag, R. Sustainable and Mass Production of Cotton Dyeing with Natural Dye (Weld) in the Textile Industry. Journal of Natural Fibers 2022, 19, 10935-10945. DOI: doi.org/10.1080/15440478.2021.2002781

Ozdemir, M.B.; Karadag, R. Madder (Rubia tinctorum L.) as an Economic Factor Under Sustainability Goals in the Textile Dyeing. Journal of Natural Fibers 2023, 20, 2128968. DOI: doi.org/10.1080/15440478.2022.2128968

Grethe, T.; Vorneweg, C.; Haase, H., Mahltig, B. Natural Antibacterials for Technical Applications. In: Antibacterials – Synthesis, Properties and Biological Activities; Collins, E. (Editor), Nova Publishers, New York, USA, 2017; pp. 91-114.

Terzioglu, F.; Grethe, T.; Both, C.; Joßen, A.; Mahltig, B.; Rabe, M. State of the art and future prospects for textile finishing. In: Handbook of Antimicrobial Coatings; Tiwari, A. (Editor), Elsevier, Amsterdam, 2018; pp. 123-136.

Kamboj, A.; Jose, S.; Singh, A. Antimicrobial activity of natural dyes–a comprehensive review. Journal of Natural Fibers 2022 19, 5380-5394. DOI: doi.org/10.1080/15440478.2021.1875378.

Gulati, R.; Sharma, S.; Sharma, R. K. Antimicrobial textile: recent developments and functional perspective. Polym. Bull. 2022, 79, 5747-5771. DOI: doi.org/10.1007/s00289-021-03826-3.

Shabbir, M.; Rather, L.J.; Azam, M.; Mohd, Q.; Haque, R.; Khan, M.A.; Mohammad, F. Antibacterial Functionalization and Simultaneous Coloration of Wool Fiber with the Application of Plant-Based Dyes. Journal of Natural Fibers 2020, 17, 437-449. DOI: doi.org/10.1080/15440478.2018.1500336.

Karadag, R. Establishing a New International Standard for Natural Dyed Textile Goods [Natural Organic Dye Standard (NODS)]. Journal of Natural Fibers 2023, 20, 1-22. DOI: doi.org/10.1080/15440478.2022.2162187.

Peets, P.; Kaupmees, K.; Vahur, S.; Leito, I. Reflectance FT-IR spectroscopy as a viable option for textile fiber identification. Heritage Science 2019, 7, 93. DOI: 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. 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. Annals of Textile Engineering and Fashion Technology 2022, 1, 1-10.

Mahltig, B.; Ernst, V.; Schröder, L. Exemplarily view on selected fluorescence textile products. Communications in Development and Assembling of Textile Products – CDATP 2023, 4, 61-69. DOI 10.25367/cdatp.2022.4.p61-69.

Jemo, D.; Parac-Ostermann, D. Identification of Natural Dyes on 18th Century Liturgical Textiles from Dubrovnik. Fibres & Textiles in Eastern Europe 2017, 25, 113-120. DOI: 10.5604/12303666.1227891.

Ahmed, H.E.; Darwish, S.S. Effect of Museum Conditions on Historical Dyed Silk Fabric with Madder Dye. J. Polym. Environ. 2012, 20, 596-606. DOI: 10.1007/s10924-012-0421-x.

Carl Roth GmbH (Karlsruhe, Germany), product web page for Alizarin. https://www.carlroth.com/de/de/ph-indikatoren/alizarin-%28c-i-%C2%A058000%29/p/4476.1 (accessed 2023-01-11).

Pflänzenfärbershop (Hückelhoven-Baal, Germany), product web page for Madder root extract. https://shop.pflanzenfaerber.eu/farbepflanzenextrakte/35-krappwurzelextrakt-rubiae-tinctoriae-radix-extractum-10g.html (accessed 2023-01-11).

Pflänzenfärbershop (Hückelhoven-Baal, Germany), product web page for Madder root pieces. https://shop.pflanzenfaerber.eu/farbepflanzen/87-krappwurzel-rubiae-tinctoriae-radix-100g.html (accessed 2023-01-11).

Kremer Pigmente GmbH (Aichstetten, Germany), product web page for ground Madder Roots. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/37201-madder-roots-ground-with-pieces.html (accessed 2023-01-11).

Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Madder Roots. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/37199-madder-roots.html (accessed 2023-01-11).

Merck (Darmstadt, Germany), product webpage for Lawsone; 2-Hydroxy-1,4-naphthochinone. https://www.sigmaaldrich.com/DE/de/product/sial/h46805?gclid=Cj0KCQiAq5meBhCyARIsAJrtdr6wi43xyQmAF4KG568ZqmHe2Ln_Dg7P-TJPk27sXDLoKxiPUOoQxC4aAoFuEALw_wcB&gclsrc=aw.ds (accessed 2023-01-18)

Pflänzenfärbershop (Hückelhoven-Baal, Germany), product web page for Henna Red. https://shop.pflanzenfaerber.eu/farbepflanzen/73-hennapulver-rot-hennae-folia-pulvis-rot-100g.html (accessed 2023-01-18)

Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Henna Red. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/37500-henna-red.html (accessed 2023-01-28)

Das Wollschaf (Zweibrücken, Germany), product web page for Henna Red. https://das-wollschaf.de/osshop/catalog/product_info.php?cPath=90_91_92&products_id=605 (accessed 2023-01-25)

Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Henna Black. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/natural-organic-dyes-vegetable-color-paints/37510-henna-black.html (accessed 2023-01-12)

Merck (Darmstadt, Germany), product webpage for Juglone; 5-Hydroxy-1,4-naphthochinone. https://www.sigmaaldrich.com/DE/de/substance/juglone17415481390 (accessed 2023-01-18)

Pflänzenfärbershop (Hückelhoven-Baal, Germany), product web page for Walnut Hull. http://shop.pflanzenfaerber.eu/farbepflanzen/115-walnussschalen-juglandis-nuc-cortex-100g.html (accessed 2023-01-18)

Kremer Pigmente GmbH (Aichstetten, Germany), product web page for Walnut Hull. https://www.kremer-pigmente.com/en/shop/dyes-vegetable-color-paints/natural-organic-dyes-vegetable-color-paints/37300-walnut-hulls.html (accessed 2023-01-23)

Das Wollschaf (Zweibrücken, Germany), product web page for Alkana. https://das-wollschaf.de/osshop/catalog/product_info.php?cPath=90_91_92&products_id=588 (accessed 2023-01-25)

Pflänzenfärbershop (Hückelhoven-Baal, Germany), product web page for Alkana. https://shop.pflanzenfaerber.eu/farbepflanzen/34-alkannawurzel-alcannae-radix-100g.html (accessed 2023-03-16).

Willmes, A. Taschenbuch Chemische Substanzen; Verlag Harri Deutsch, Thun, 1993.

Seilnacht, T. Pigmente und Bindemittel, Seilnacht Verlag & Atelier, Bern, 2018.

Zarkogianni, M.; Mikropoulou, E.; Varella, E.; Tsatsaroni, E. Colour and fastness of natural dyes: revival of traditional dyeing techniques. Coloration Technol. 2010, 127, 18-27. DOI: 10.1111/j.1478-4408.2010.00273.x.

Jahangiri, A.; Ghoreishian, S. M.; Akbari A.; Norouzi, M.; Ghasemi, M.; Ghoreishian, M.; Shafiabadi, E. Natural dyeing of wool by madder (rubia tinctorum l.) root extract using tannin-based biomordants: Colorimetric, fastness and tensile assay. Fibers and Polymers 2018, 19, 2139-2148. DOI: 10.1007/s12221-018-8069-3.

Shahi, Z.; Mehrizi, M.K.; Hadizadeh, M. A Review of the Natural Resources Used to Hair Color and Hair Care Products. J. Pharm. Sci. & Res. 2017, 9, 1026-1030.

Fischer Scientific UK, web page with safety data sheet for aliziarin.

https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&ved=2ahUKEwir54Cz5I-AAxXwhf0HHRJxCjEQFnoECA8QAQ&url=https%3A%2F%2Fwww.fishersci.at%2FchemicalProductData_uk%2Fwercs%3FitemCode%3D13418388%26lang%3DDE&usg=AOvVaw0awjYbzayUcaAsVrqC_2pv&opi=89978449 (accessed 2023-07-15).

Montazer, M.; Parvinzadeh, M. Effect of ammonia on madder‐dyed natural protein fiber. J. Appl. Polym. Sci. 2004, 93, 2704-2710. DOI: doi.org/10.1002/app.20880.

Montazer, M.; Taghavi, F. A.; Toliyat, T.; Moghadam, M. B. Optimization of dyeing of wool with madder and liposomes by central composite design. J. Appl. Polym. Sci. 2007, 106, 1614-1621. DOI: doi.org/10.1002/app.26841.

Zhu, S.; Huang, Z.; Yu, X.; Wei, L.; Wang, H.; Huang, S.; Meng, X.; Han, Y. pH-responsive fibre dyed by natural madder dye. Coloration Technology 2022, 38, 304-314.

Ibrahim, N. A.; El-Gamal, A. R.; Gouda, M.; Mahrous, F. A new approach for natural dyeing and functional finishing of cotton cellulose. Carbohydrate Polymers 2010, 82, 1205-1211. DOI: 10.1016/j.carbpol.2010.06.054.

Yusuf, M.; Shahid, M.; Khan, M. I.; Khan, S. A.; Khan, M. A.; Mohammad, F. Dyeing studies with henna and madder: A research on effect of tin (II) chloride mordant. J. Saudi Chem. Soc. 2015, 19, 64-72. DOI: doi.org/10.1016/j.jscs.2011.12.020.

Imani, H.; Gharanjig, K.; Ahmadi, Z. A novel efficient method for eco-friendly deep dyeing of wool yarns by extracted madder dyes in the presence of additives. Industrial Crops and Products 2022, 183, 114970. DOI: doi.org/10.1016/j.indcrop.2022.114970.

Hosseinnezhad, M.; Gharanjig, K.; Razani, N.; Imani, H. Green Dyeing of Wool Fibers with Madder: Study of Combination of Two Biomordant on K/S and Fastness. Fibers and Polymers 2020, 21, 2036-2041. DOI: 10.1007/s12221-020-9311-3.

Hosseinnezhad, M.; Gharanjig, K.; Belbasi, S.; Seied Saadati, S.H. Green Dyeing of Silk Fabrics in the Presence of Pomegranate Extract as Natural Mordant. Prog. Color Colorants Coat. 2017, 10, 129-133. DOI: 10.30509/pccc.2017.75717.

Hosseinnezhad, M.; Gharanjig, K.; Jafari, R.; Imani, H. Green dyeing of woolen yarns with weld and madder natural dyes in the presences of biomordant. Progr. Color Colorants Coat. 2021, 14, 35-45. DOI: 10.30509/pccc.2021.81678.

Hosseinnezhad, M.; Gharanjig, K.; Rouhani, S.; Razani, N.; Imani, H. Environmentally friendly dyeing of wool yarns using of combination of bio‐mordants and natural dyes. Environmental Progress & Sustainable Energy 2022, 4, e13868. DOI: doi.org/10.1002/ep.13868.

Gupta, V.; Jose, S.; Kadam, V.; Shakyawar, D. B. Sol gel synthesis and application of silica and titania nano particles for the dyeing and UV protection of cotton fabric with madder. Journal of Natural Fibers 2022, 19, 5566-5576. DOI: doi.org/10.1080/15440478.2021.1881688.

Trepte, J.; Böttcher, H. Improvement in the leaching behavior of dye-doped modified silica layers coated onto paper or textiles. J. Sol-Gel Sci. & Technol. 2000, 19, 691-694. DOI: doi.org/10.1023/A:1008766807514.

Mahltig, B.; Knittel, D.; Schollmeyer, E.; Böttcher, H. Incorporation of triarylmethane dyes into sol–gel matrices deposited on textiles. J. Sol-Gel Sci. & Technol. 2004, 31, 293-297. DOI: doi.org/10.1023/B:JSST.0000048006.70681.7c.

Mahltig, B.; Textor, T. Combination of silica sol and dyes on textiles. J. Sol-Gel Sci. & Technol. 2006, 39, 111-118. DOI: doi.org/10.1007/s10971-006-7744-9.

Yuan, W.; Grethe, T.; Mahltig, B. Sol-gel coatings with the fluorescence dye Rhodamine B for optical modification of cotton. Communications in Development and Assembling of Textile Products – CDATP 2023, 4, 1-17. DOI: doi.org/10.25367/cdatp.2023.4.p1-17.

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.

Cyranski, M.K.; Jamroz, M.H.; Rygula, A.; Dobrowolski, J.C.; Dobrzycki, L.; Baranska, M. On two alizarin polymorphs. Cryst. Eng. Comm. 2012, 14, 3667-3676. DOI: 10.1039/c2ce06063a.

Mahkam, M.; Nabati, M.; Kafshboran, H.R. Isolation, identification and characterization of lawsone from henna leaves powder with Soxhlet technique. Iranian Chemical Communication 2014, 2, 34-38.

Trueb, L.F. Pflanzliche Naturstoffe, Borntraeger Verlagsbuchhandlung, Stuttgart, 2015.

Panfili, E.; Esposito, S.; Di Cara, G. Temporary black henna tattoos and sensitization to para-phenylenediamine (PPD): two paediatric case reports and a review of the literature. International Journal of Environmental Research and Public Health 2017, 14, 421. DOI: 10.3390/ijerph14040421.

De Groot, A.C. Side‐effects of henna and semi‐permanent ‘black henna’tattoos: a full review. Contact Dermatitis 2013, 69, 1-25. DOI: 10.1111/cod.12074.

Mudi, S. Y.; Ibrahim, H.; Bala, M. S. Acute toxicity studies of the aqueous root extract of Lawsonia inermis Linn. in rats. Journal of Medicinal Plants Research 2011, 5, 5123-5126.

Badri, B. M.; Burkinshaw, S. M. Dyeing of wool and nylon 6.6 with henna and lawsone. Dyes and Pigments 1993, 22, 15-25. DOI: doi.org/10.1016/0143-7208(93)80009-P.

Yusuf, M.; Ahmad, A.; Shahid, M.; Khan, M. I.; Khan, S. A.; Manzoor, N.; Mohammad, F. Assessment of colorimetric, antibacterial and antifungal properties of woolen yarn dyed with the extract of the leaves of henna (Lawsonia inermis). Journal of Cleaner Production 2012, 27, 42-50. DOI: doi.org/10.1016/j.jclepro.2012.01.005.

Alebeid, O.K.; Pei, L.; Zhou, W.; Wang, J. Sustainable wool fibers dyeing using henna extract in non-aqueous medium. Environmental Chemistry Letters 2020, 18, 489-494. DOI: doi.org/10.1007/s10311-019-00949-y.

Bhuiyan, M.A.R.; Ali, A.; Islam, A.; Hannan, M.A.; Kabir, S.M.F.; Islam, M.N. Coloration of polyester fiber with natural dye henna (Lawsonia inermis L.) without using mordant: a new approach towards a cleaner production. Fashion and Textiles, 2018, 5, 2. DOI: doi.org/10.1186/s40691-017-0121-1.

Saadaoui, S.; Youssef, M.A.B.; Karoui, M.B.; Gharbi, R.; Smecca, E.; Strano, V.; Mirabella, S.; Alberti, A.; Puglisi, R.A. Performance of natural-dye-senisitized solar cells by ZnO nanorod and nanowall enhanced photoelectrodes. Beilstein Journal of Nanotechnology 2017, 8, 287-295. DOI: 10.3762/bjnano.8.31.

Dama, L.B. Effect of naturally occurring napthoquinones on root-knot nematode Meloidogyne javanica. Indian Phytopath. 2002, 55, 67-69.

Wright, D.A.; Michelmore, C.L.; Dawson, R.; Cutler, H.G. The influence of water quality on the toxicity and degradation of juglone (5-hydroxy 1,4-napthoquinone). Environmental Technology 2007, 28, 1091-1101.

Mirjalili, M.; Nazarpoor, K.; Karimi, L. Extraction and identification of dye from walnut green husks for silk dyeing. Asian Journal of Chemistry 2011, 23, 1055.

Fernández-Agulló, A.; Pereira, E.; Freire, M. S.; Valentao, P.; Andrade, P. B.; González-Álvarez, J.; Pereira, J. A. Influence of solvent on the antioxidant and antimicrobial properties of walnut (Juglans regia L.) green husk extracts. Industrial Crops and Products 2013, 42, 126-132. DOI: doi.org/10.1016/j.indcrop.2012.05.021.

Bukhari, M.N.; Islam, S.; Shabbir, M.; Rather, L.J.; Shahid, M.; Singh, U.; Khan, M. A.; Mohammad, F. Dyeing studies and fastness properties of brown naphthoquinone colorant extracted form Juglans regia L on natural protein fiber using different metal salt mordants. Textiles and Clothing Sustainability 2017, 3, 3. DOI: 10.1186/s40689-016-0025-2.

Ebrahimi, I.; Gashti, M.P. Extraction of juglone from Pterocarya fraxinifolia leaves for dyeing, anti-fungal finishing, and solar UV protection of wool. Coloration Technol. 2015, 131, 451-457. DOI: 10.1111/cote.12180.

Arifeen, W.-U.; Rehman, F.U.; Adeel, S.; Zuber, M.; Ahmad, M.N.; Ahmad, T. Environmental friendly extraction of walnut bark-based juglone natural colorant for dyeing studies of wool fabric. Environmental Science and Pollution Research 2021, 28, 49958-49966. DOI: doi.org/10.1007/s11356-021-14277-8.

Gupta, D.B.; Gulrajani, M.L. Studies on dyeing with natural dye Juglone (5-hydroxy-1,4-napthoquinone). Indian Journal of Fibre & Textile Research 1993, 18, 202-206.

Lal, C.; Raja, A.S.M.; Pareek, P.K.; Shakyawar, D.B.; Sharma, K.K.; Sharma, M.C. Juglans nigra: Chemical constitution and its application on Pashmina (Cashmere) fabric as a dye. J. Nat. Prod. Plant Resour. 2011, 1, 13-19.

Mirjalili, M.; Nazarpoor, K.; Karimi, L. Extraction and Identification of Dye from Walnut Green Husks for Silk Dyeing. Asian Journal of Chemistry 2011, 23, 1055-1059.

Eser, F.; Onal, A.; Oztav, F. Investigation of the dyeing properties of wool fabrics with Alkanna tinctorial root extract. International Journal of Science Letters 2021, 3, 1-17. DOI: doi.org/10.38058/ijsl.786969.

Adeel, S.; Kiran; S., Alam; M., Farooq, T.; Amin, N.; Gulzar, T. Alkanna tinctoria-based sustainable alkanin natural colorant for eco-dyeing of wool. Environmental Science and Pollution Research 2022 1-8. DOI: doi.org/10.1007/s11356-022-23806-y.

Rehman, F.-U.; Adeel, S.; Liaqat, S.; Hussaan, M.; Mia, R.; Ahmed, B.; Wafa, Environmental friendly bio-dyeing of silk using Alkanna tinctoria based Alkannin natural dye. Industrial Crops and Products 2022, 186, 115301. DOI: doi.org/10.1016/j.indcrop.2022.115301.

Haldhar, R.; Prasad, D.; Saxena, A.; Kaur, A. Corrosion resistance of mild steel in 0.5 M H2SO4 solution by plant extract of Alkana tinctoria: experimental and theoretical studies. Eur. Phys. J. Plus 2018, 133, 1-18. DOI: 10.1140/epjp/i2018-12165-0.