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Rubia Tinctorum in Wool

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Rubia Tinctorum in Wool The chemical profile of Rubia tinctorum in wool dyeing and a novel fibre extraction method for compositional analysis Robert Lee Henderson Submitted in accordance with the requirements for the degree of Doctor of Philosophy The University of Leeds School of Design September 2013 The candidate confirms that the work submitted is his own and that appropriate credit has been given where reference has been made to the work of others. This copy has been supplied on the understanding that it is copyright material and that no quotation from the thesis may be published without proper acknowledgement © 2013 The University of Leeds and Robert Lee Henderson The right of Robert Lee Henderson to be identified as Author of this work has been asserted by him in accordance with the Copyright, Designs and Patents Act 1988. I Abstract This report describes the understanding of natural dyes and the work necessary for analysis of historical textiles. Chapter 1 provides a general introduction into the background of historical dyeing, the methods used to extract these natural dye compounds used and how synthetic dyes overtook natural dyes in the commercial world of dyeing. Chapter 2 introduces and discusses the research undertaken with one particular natural dyeing plant, Rubia tinctorum (common madder). Dyeing studies were all performed on wool, and explore the dyeing properties of the madder plant. Dyeing studies with pre-mordanting and post-mordanting were undertaken. Chapter 3 explores the extraction of natural dyes from Rubia tinctorum and their identification. Extraction and analysis studies were conducted to obtain the ideal method for acquiring glycosidic anthraquinone dye molecules that could be used in the dyeing process. Chapter 4 focuses on identifying new methods to successfully remove glycosidic anthraquinone dye compounds from wool fibres dyed with Rubia tinctorum, whilst keeping their chemical structure intact. Further work in this chapter is undertaken to analyse glycosidic anthraquinone dye compounds successfully removed from photo- degraded wool fibres and the comparison with current literature techniques used for historical sample analysis. II Acknowledgements Firstly I would like to thank Dr. Richard Blackburn and Professor Chris Rayner for giving me this opportunity to do this PhD. I would also like to thank them for their constant support and guidance throughout my first year. Secondly I would like to thank the Clothworkers’ Company for providing the funding for this research and subsequently for their continuous interest in the project. I would also like to thank Dr. Paul “Aglet” Rose for his never ending help and his unwavering knowledge in the field of chemistry and dyes. Dr. Thomas “Catan” Farmer for all the help not just with my report, but also his knowledge and understanding of all things chemistry plus making me look so good in the lab. The “GOD” over in the design building without whom I would never have got started and would still be trying to figure out how to use the dyeing machines. I would also like to thank all the people in both the Blackburn and Rayner groups especially Liam McCallister for his never ending helping and chats about anthraquinones plus always helping me find equipment even when it was right under my nose. I would also like to thank Aoife Hannigan for being a constant pillar of support throughout my PhD studies. Thank you for all the conversations when times were hard, for all the reassurances when I had moments of doubt and the times spent away from my studies just to give me a break. Those trips down to London were ultimately what got me through my studies and will forever stay with me. I will never be able to truly express how much I appreciated you being there through it all with me. Thank you!! III I would also like to say a huge thank you to all my family and for always being there to put a smile on my face. They have helped me all through my life and have given me extreme confidence and support not just through this PhD but also through my first degree that laid the foundations for me to able to accomplish everything I have up to date. I will be forever truly grateful to you all especially to my mum who has sacrificed so much for me and has given me everything I’ve asked for and so much more. IV Table of Contents 1. INTRODUCTION ........................................................................................................ 1 1.1. HISTORY OF TEXTILE DYEING .................................................................................. 1 1.1.1. Dyeing methods and natural dyes..................................................................... 4 1.1.2. Rubia tinctorum and the history of this famous red dye................................. 10 1.2. DYEING OF WOOL .................................................................................................. 14 1.2.1. Wool structure................................................................................................. 14 1.2.2. Mordanting process ........................................................................................ 16 1.2.3. Dye interactions with wool ............................................................................. 21 1.3. EXTRACTION OF NATURAL DYES............................................................................ 23 1.3.1. Historical procedures ..................................................................................... 23 1.3.2. A modern extraction of Rubia tinctorum ........................................................ 29 1.4. ANALYSIS OF HISTORICAL TEXTILES...................................................................... 30 1.4.1. Methods of analysis ........................................................................................ 30 1.4.2. Conclusions of analysis of historical textiles.................................................. 35 1.5. EXTRACTION OF DYE COMPOUNDS BY IONIC LIQUIDS ........................................... 36 1.6. AIMS OF THIS RESEARCH ........................................................................................ 37 2. DYEING WITH RUBIA TINCTORUM.................................................................... 38 2.1. BACKGROUND ........................................................................................................ 38 2.2. DYEING................................................................................................................... 38 2.2.1. Dyeing Studies of Synthetic Alizarin and Madder.......................................... 38 2.2.2. Dyeing Studies of Fresh Ground Madder Root .............................................. 46 2.2.3. Dyeing Study of Alizarin vs. Alizarin Glucoside............................................. 54 2.2.3.1. Nernst isotherm..................................................................................................................... 57 2.2.3.2. Langmuir Isotherm................................................................................................................ 58 2.2.3.3. Freundlich Isotherm.............................................................................................................. 60 IV 2.2.4. Isotherm Results of Dyeing with Alizarin and Alizarin Glucoside onto Wool With and Without a Pre-Mordant ................................................................................. 62 2.3. CONCLUSIONS ........................................................................................................ 66 3. EXTRACTION OF RUBIA TINCTORUM .............................................................. 68 3.1. EXTRACTION AND ANALYSIS ................................................................................. 68 3.1.1. Solvent Studies of Rubia tinctorum................................................................. 68 3.1.2. Water and Ethanol Used for the Extraction of Rubia tinctorum .................... 71 3.1.3. pH Studies of Known Samples ........................................................................ 81 3.1.4. Studies on Ruberythric Acid ........................................................................... 88 3.1.5. Recrystallisation studies of entry A4 .............................................................. 90 3.1.6. X-ray Crystallography Data of Lucidin Primeveroside ................................. 94 3.2. CONCLUSIONS ........................................................................................................ 97 4. ANALYSIS OF DYED WOOL SAMPLES.............................................................. 98 4.1. BACKGROUND ........................................................................................................ 98 4.2. BACK EXTRACTIONS .............................................................................................. 98 4.2.1.1. Analysis of the Madder Extract Before and After Dyeing ................................................... 99 4.2.2. Back Extraction of Wool Samples Dyed with Madder.................................. 102 4.2.2.1. Initial Back Extractions Using Known Methods ................................................................ 102 4.2.2.2. A Further Study into the Back Extractions of Dyed Wool with Madder Extract............... 113 4.2.2.3. Back Extractions Using Different Natural Sugar Compounds ........................................... 124 4.2.2.4. Back Extractions Using Different Molarities of HCl in H2O/MeOH................................. 128 4.2.2.5. Observations of wool dyeings with SEM ..........................................................................
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