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The effect of light and dye composition on the color of dyeings with indigo, 6-bromoindigo, and 6,6′-dibromoindigo, components of Tyrian purple

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Abstract

Quantitative HPLC and colorimetry are used to study color variations in dyeings with indigo, 6-bromoindigo, and 6,6′-dibromoindigo, the main components of the historic dye Tyrian purple. For the first time, visible light is identified conclusively as a cause of debromination of the leuco form of 6-bromoindigo. A dyeing run using 6-bromoindigo alone is found to yield a dyed fabric containing large amounts of indigo, when the vat is exposed to visible light. The extent of debromination is dependent upon the pH of the dye bath and also the source of the visible light. This information allowed development of a dyeing procedure which is demonstrated to give consistent colors through two passes. Quantitative HPLC analysis of extracts from the dyed fabrics indicates that the leuco form of 6-bromoindigo vs. the leuco forms of indigo and 6,6′-dibromoindigo has the strongest affinity for wool fabric. This is postulated to be due to attractive electrostatic interactions between the leuco form of 6-bromoindigo and wool.

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Acknowledgments

Ms. Jo Kirby, formerly of The National Gallery, London, and Mr. Greg Rohaus of Konica Minolta are thanked for helpful discussions. Dr. Frank Jacob of Queensborough Community College is thanked for translating articles in Japanese. Akn Fabrics Inc. is thanked for supplying the wool fabric.

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Authors and Affiliations

  1. Department of Natural Sciences, Baruch College of the City University of New York, Box A0506, 1 Bernard Baruch Way, New York, NY, 10010, USA

    Keith Ramig, Aygul Islamova & John Scalise

  2. Department of Chemistry, Queensborough Community College of the City University of New York, 222-05 56th Ave., Bayside, New York, NY, 11364, USA

    Sasan Karimi

  3. Department of Biochemistry and Molecular Pharmacology, New York University School of Medicine, 180 Varick Street, Room 641, New York, NY, 10014, USA

    Olga Lavinda

  4. 59 Swiss Avenue, Watford, Hertfordshire, England, WD18 7LL, UK

    Christopher Cooksey

  5. University Ecclesiastical Academy of Thessaloniki, 54250, Thessaloniki, Greece

    Athina Vasileiadou & Ioannis Karapanagiotis

Authors
  1. Keith Ramig
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  2. Aygul Islamova
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  3. John Scalise
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  4. Sasan Karimi
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  5. Olga Lavinda
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  6. Christopher Cooksey
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  7. Athina Vasileiadou
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  8. Ioannis Karapanagiotis
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Correspondence to Keith Ramig or Ioannis Karapanagiotis.

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Additional information

This article is dedicated to our colleague and friend Professor Lou Massa, in honor of his 75th birthday. Lou kindly introduced this project to three of us (KR, OL, and SK) and collaborated in much of the previous work on it.

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Ramig, K., Islamova, A., Scalise, J. et al. The effect of light and dye composition on the color of dyeings with indigo, 6-bromoindigo, and 6,6′-dibromoindigo, components of Tyrian purple. Struct Chem 28, 1553–1561 (2017). https://doi.org/10.1007/s11224-017-0932-0

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  • DOI: https://doi.org/10.1007/s11224-017-0932-0

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