Late 's. Took Place Here. The origins of the Brooklyn synthetic dye industry can be traced back to the efforts of Dr. August F. Partz, a German chemist who obtained two U.
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Textile Engineering & Fashion Technology
Metrics details. Natural indigoids such as indigo, woad, and Tyrian or shellfish purple served this purpose for millennia, but in the late s synthetic analogs, in particular indigotin, quickly replaced natural sources. Interestingly, these have not been significantly discussed in the literature, nor have they been found in forensic or technical art history investigations of textiles until now.
This paper reports the first identification in a museum context of this unusual synthetic brominated analog of indigo, discovered on three twentieth century Japanese yukata. Analytical data collected on reference materials using liquid chromatography-mass spectrometry, UV—visible spectroscopy, Raman microspectroscopy, Fourier transform infrared spectroscopy, and X-ray fluorescence spectroscopy are provided to assist with future identifications of this relatively unknown colorant.
The colors blue and purple have historically been prized in textile dyeing and have led to millennia of human exploration for new sources of these colored dyestuffs. Natural indigotin Fig. Natural indigo has traditionally been obtained from oxidation of precursor compounds isolated from the fermentation of macerated leaves of plants like Indigofera tinctoria , Isatis tinctoria, and Polygonum tinctoria [ 1 , 3 ], which are widely distributed around the globe.
Creating a colorant from indigo involves chemically reducing the insoluble indigotin to a water soluble leuco -form that can penetrate into the interstitial space within the fiber of a textile.
Re-oxidation of the leuco -indigotin by air or chemical means returns the compound to its insoluble form, trapping the colorant within the fiber.
Indigoids in the solid state are relatively photochemically inert and remain insoluble in aqueous and many organic solvents, making indigo dyed textiles both lightfast and wash resistant [ 1 ]. Depending on the number of repetitions through the dye bath, indigo can produce various shades of blue, ranging from sky blue to deep ocean blue and even black [ 1 ]. Additionally, indigo has traditionally been combined with a yellow or red dye to obtain green and purple colors, respectively [ 1 ].
Outside of being a textile dye, indigo is used to color leather, paint, and ink, to make cosmetics, and to treat illnesses as a folk medicine [ 1 ]. As a pigment suitable for nearly all media, its use can be found in Asian, Western, South American, and African artworks throughout time.
In the late s, chemical synthesis of new dyes provided inexpensive and readily available color alternatives, which competed with and quickly replaced their natural counterparts.
Studies on the chemical structure of natural indigo in Germany eventually led to its successful synthesis by Adolf von Bayer in the early s [ 5 ]. The European synthetic dye industry thrived. At the start of WWI, the Dow Chemical Company, which was based in Midland Michigan, saw that there would soon be a shortage of the dyes used by the textile makers in the USA and embarked on an effort to establish a manufacturing process using their own chemical building blocks for making synthetic indigo.
After several years of intensive laboratory investigation, their chemists evolved a complete synthesis of the dye based on the Heumann process. The operation of the indigo plant on a commercial scale was an acknowledged success in December, , thus initiating the first production of synthetic indigo in the USA [ 7 ]. The determination of the chemical composition of indigo, with its resultant commercial production, placed in the hands of the chemist a new basic material.
Derivatization of organic colorants can lead to dyes with new shades of color, improved fiber binding, and better lightfastness.
As the demand for indigo grew, derivatives were synthesized [ 5 ], and some were marketed [ 8 , 9 , 10 , 11 ]. Bromination or chlorination was found to yield products which dyed cloth further to the red or green shades and enhanced considerably the fastness.
This last addition to the projects of the Dow Chemical Company completed the series of blue dyes of the indigo group [ 11 ]. However, among those brominated derivatives of indigotin that were patented worldwide [ 13 ], it would appear that none of these made a significant and lasting commercial impact or challenged the supremacy of synthetic indigo as suggested by the scant scientific, trade, or industrial literature pertaining to them. In a telling example, a forensic study used absorption microspectrophotometry to search for indigo and its derivatives in samples from blue denim garments of various brands and manufacturers from Asia, Europe, and America [ 14 ].
The researchers found only indigotin, suggesting that rarely have the halogenated indigos been used as dyestuffs for denim in modern times. One of these, shown in their paper as Fig. Although fashion interest in these brominated indigos appears not to have been strong in the West, indigo and its halogenated analogs have recently been explored as possible additives to organic semiconductors [ 16 ], arguing for a more complete characterization of these dyes.
In preparation for a recent museum exhibition on the chemistry of color, scientists at the Indianapolis Museum of Art IMA at Newfields investigated four blue Japanese yukata as possible examples of artworks colored with indigo. Yukata are traditional Japanese summer garments that generally resemble silk kimonos, but are less formal and are often woven from cotton. Those with a deep blue coloration are usually thought to be dyed with indigo.
To achieve a pattern, the textile is tightly gathered and methodically stitched or bound creating a physical resist that protects the fabric from dye penetration.
The bound textile is then immersed into a dye bath, presumably indigo. Upon completion of the dye cycle the protective binding materials are removed and the undyed white patterned fabric is revealed. To specify the presence of natural or synthetic indigo, chemical studies were performed on blue threads from these garments. Surprisingly, the results from two of the four robes indicated that the dye was not indigo, but rather an unusual blue halogenated derivative little discussed in the scientific literature and unknown in technical art history.
The two relevant yukata are shown in Fig. Two cotton yukata dyed using the shibori method. Gift of Jeffery Krauss. Photo courtesy of Newfields. Synthetic indigotin C. A modern commercial sample was also obtained from the Sigma Aldrich Rare Chemical Library with no guarantee of purity or accuracy of contents PH After cooling, the almost colorless fiber was discarded, and the blue DMSO extract was filtered through a 0.
Reference material powders were similarly dissolved, heated, and filtered. Nitrogen sheath and auxiliary gases for the MS were delivered from a gas generator Peak Scientific at Considering the limited sample from artworks, the slow gradient elution was designed for detecting and identifying all possible extractable compounds from the sample in a single run. A solvent blank was run immediately before each sample to confirm there was no carryover.
CID was set to target singularly charged ions using an isolation width of 2. Raman spectra were acquired using a Bruker Senterra microspectrometer on a Z-axis gantry. A 50X ultra-long working distance objective was used to focus on dye agglomerates located on fiber samples or on pigment particles for neat samples of the dyes.
OPUS software allowed for automated cosmic spike removal, peak shape correction, and spectral calibration. Microsamples were crushed on a diamond compression cell and held on a single diamond window during the analysis. A vacuum attachment allowed for light element detection.
Analysis of the fiber extracts was performed for the original sample set of 4 yukata with the expectation that all would be dyed using natural or synthetic indigo. One of the textiles was found to contain indigo, and one contained a synthetic dye not shown that did not have the spectroscopic properties of an indigoid.
The robes shown in Fig. Comparison with the chromatogram for synthetic indigotin row 3 reveals that the yukata dye is not indigo. Spectra presented were subjected to a baseline correction routine that included a two-range subtraction using the regions immediately before and after the occurrence of the chromatographic peak.
Comparison of the data from the two yukata Fig. However, the yukata are a deep blue color and not purple, which is reflected in the solution absorption spectra of their dye extract as seen in the DAD data in the middle column of Fig.
Two other possible explanations for the anomalous color can be discounted based on the LC—MS experiment. First, only a single major chromatographic peak exists for the blue yukata dyes, ruling out the possibility of a dye mixture such as indigo and Tyrian purple.
Moreover, the FSMS spectra of the yukata dyes clearly indicate a dibrominated species in each instance. This dye has not appeared previously in cultural heritage studies and was unknown at the time by the authors. They surpass indigo in brilliancy, fastness, and affinity for the fibre. These dyes were marketed for their excellent fastness to acid, alkali, soap, light, and resistance to chlorine bleach.
The lower brominated products show close relationship to indigo, both as regards to their tinctorial behavior and their fastness. Company trade advertisements from the time, Fig. The exact dates of production for Midland Blue R could not be discovered, although company records indicate that it was still in production in along with the tetrabrominated Ciba Blue 2B [ 18 ]. Furthermore, a photograph found in the Dow archives held by the Chemical Heritage Foundation indicates production beyond that date.
Dow Chemical Company is said to have ended its indigoid dye manufacturing in the early s [ 8 ]. Samples of the colorant were acquired to compare to the dye extract from the two yukata.
The dye may even represent an as yet unknown Asian producer, but this can only be speculation at this point. Only the data from one yukata is provided, although both garments yielded identical results. It is clear from the comparison in Fig. However, the spectrum not shown revealed small band shifts and intensity variations compared to that of the dried extract. This has been reported for indigo as well where it was attributed to changes in the planarity of the molecule upon interaction with the fiber [ 15 ].
Peak wavenumbers are provided for the two isomers of DBI. For clarity, all vibrational modes from the DFT calculation are shown, but the Raman active modes are indicated by their A g and B g symmetries. The scaled calculated data represent the best fit between experiment and theory. Direct analysis of the dyed cotton fiber using FTIR attenuated total reflection ATR spectroscopy provided a spectrum dominated by cellulose with only a few very weak bands indicating the presence of the dye not shown.
Even when the undyed fiber was used for spectral subtraction, the resulting spectrum of the dye was noisy and yielded only the highest intensity IR bands. To confirm the identification and provide valuable reference data, FTIR microspectroscopy was performed on the dried crystallites obtained by extracting the yukata textile fibers with DMSO. These additional spectral features from the yukata dye are likely due to an unidentified organic material that was inadvertently leached from the fiber along with the blue dye by the DMSO extraction.
It is possible that an organic residue from the shibori dying or possibly a fabric treatment applied post dyeing could exist on the finished fiber. The question remains how common this dye might be in traditional twentieth century Japanese fashion.
To facilitate surveys of large museum textile collections, pXRF was explored as a rapid, sensitive, and non-invasive analytical technique capable of identifying blue brominated indigoids on museum textiles.
The potential for interferences from other brominated non-indigoid dyes or brominated fiber treatments was considered unlikely. The intensity of the Br signal relative to the background and scattered radiation suggests even shorter experiments could be used for the non-invasive screening for blue brominated dyes. Only a very weak Br signature was detected in the mostly white areas of the same garment as seen in Fig.
The spectra have been offset for clarity. One additional cotton yukata , Fig. The white cotton fabric in this yukata is a plain weave, with a pattern of deep blue squares and thin blue S-curve lines achieved not by the shibori method in this instance, but through the use of a paste resist applied through stencils to protect the white fabric from dye penetration.
The cloth was then immersed into a dye bath. Once the paste resist was removed the deep blue squares and curves are revealed.
The object was originally dated by the donor to the late Meiji Period —
Indigo dye is an organic compound with a distinctive blue color see indigo. Historically, indigo was a natural dye extracted from the leaves of certain plants, and this process was important economically because blue dyes were once rare. A large percentage of indigo dye produced today, several thousand tonnes each year, is synthetic. It is the blue often associated with denim cloth and blue jeans.
Metrics details. Natural indigoids such as indigo, woad, and Tyrian or shellfish purple served this purpose for millennia, but in the late s synthetic analogs, in particular indigotin, quickly replaced natural sources. Interestingly, these have not been significantly discussed in the literature, nor have they been found in forensic or technical art history investigations of textiles until now. This paper reports the first identification in a museum context of this unusual synthetic brominated analog of indigo, discovered on three twentieth century Japanese yukata. Analytical data collected on reference materials using liquid chromatography-mass spectrometry, UV—visible spectroscopy, Raman microspectroscopy, Fourier transform infrared spectroscopy, and X-ray fluorescence spectroscopy are provided to assist with future identifications of this relatively unknown colorant.
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Until the mids, all dyes came from natural sources, such as insects, roots, or minerals. Producing them was difficult and expensive. In , an year-old English chemist, William Henry Perkin, accidentally discovered one of the first synthetic dyes. In search of a treatment for malaria, Perkin experimented with coal tar, a thick, dark liquid by-product of coal-gas production.
Regret for the inconvenience: we are taking measures to prevent fraudulent form submissions by extractors and page crawlers. Received: August 18, Published: July 14, Citation: Choudhury AKR. Green chemistry and textile industry. J Textile Eng Fashion Technol. DOI: Download PDF. Contrary to non-sustainable, non-renewable fossil fuel-based conventional chemical processes, green reactions are sustainable, highly efficient fewer steps, fewer resources, less waste , much easy-to-use stable under ambient conditions and very much eco-friendly non-hazardous solvents and less hazardous minimized waste. They are assessed by twelve principles. The textile industry is considered as ecologically one of the most polluting industries in the world. Recently a number of steps have been taken to make textile processing greener.
Analytical characterization of 5,5′-dibromoindigo and its first discovery in a museum textile
Move the mouse pointer over a red word in the main text, to view the glossary entry for this word. Advances in organic chemistry in the 19th century prompted a revolution in German industry. Until the middle of the century the expanding textiles industry had used natural dyestuffs. While England and France were able to draw the required raw materials from their colonial empires, Germany was largely forced to rely on imports. The first artificial dye, mauveine, was developed by William Henry Perkin in The basic product for refining artificial dyes was aniline, which is derived from black coal. Coal tar, until then a waste product, was discovered to contain the aniline that could be used in producing coal-tar dyes. This led to a gradual liberation from natural raw materials and, in Germany, to the concerted building of aniline factories and the development of artificial dyestuffs.
Chemical building blocks and useful products
Textile industries are responsible for one of the major environmental pollution problems in the world, because they release undesirable dye effluents. Textile wastewater contains dyes mixed with various contaminants at a variety of ranges. Therefore, environmental legislation commonly obligates textile factories to treat these effluents before discharge into the receiving watercourses. The treatment efficiency of any pilot-scale study can be examined by feeding the system either with real textile effluents or with artificial wastewater having characteristics, which match typical textile factory discharges. This paper presents a critical review of the currently available literature regarding typical and real characteristics of the textile effluents, and also constituents including chemicals used for preparing simulated textile wastewater containing dye, as well as the treatments applied for treating the prepared effluents. This review collects the scattered information relating to artificial textile wastewater constituents and organises it to help researchers who are required to prepare synthetic wastewater. These ingredients are also evaluated based on the typical characteristics of textile wastewater, and special constituents to simulate these characteristics are recommended. The processes carried out during textile manufacturing and the chemicals corresponding to each process are also discussed. Textile industries positively affect the economic development worldwide. However, one of the problems associated with textile factories is the unacceptable effluent, especially dyes, which are difficult to degrade.
Paris, April 25th, Living colors: Biotech dyes help the textile industry go green.
Even benign chemicals like potato starch will kill fish and other aquatic life because they encourage the growth of algae which depletes all available oxygen, among other issues known as BOD or Biological Oxygen Demand. So be sure to buy fabric from a supplier who has water treatment in place. The other part of the equation is how the dye is formulated, because if toxic chemicals are used in the formulation then most of these chemicals remain in the fabric. If synthetic chemical dyestuffs contain chemicals which can poison us, then the use of natural dyes seems to many people to be a safer alternative.
Substantially revising and updating the classic reference in the field, this handbook offers a valuable overview and myriad details on current chemical processes, products, and practices. No other source offers as much data on the chemistry, engineering, economics, and infrastructure of the industry. The Handbook serves a spectrum of individuals, from those who are directly involved in the chemical industry to others in related industries and activities. Industrial processes and products can be much enhanced through observing the tenets and applying the methodologies found in new chapters on Green Engineering and Chemistry, Practical Catalysis, and Environmental Measurements; as well as expanded treatment of Safety and Emergency Preparedness.
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