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ABSTRACT LI, MIN. Forensic Analysis of Organic Dyes on Trace Fibers

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ABSTRACT LI, MIN. Forensic Analysis of Organic Dyes on Trace Fibers ABSTRACT LI, MIN. Forensic Analysis of Organic Dyes on Trace Fibers and Their Photodegradation. (Under the direction of David Hinks and Nelson. R. Vinueza.) Trace evidence collected from difference sources (victims, suspects and the crime scene) can establish connections between the crime scene, suspects and victims if they are identical. In forensic analysis, textile fiber evidence is compared in terms of both physical properties and chemical composition, among which the organic dyes are important components. Therefore unambiguous identification of organic dyes is of significance in forensic fiber analysis. The dye concentration present in trace fibers is extremely low. Therefore, highly sensitive, efficient and accurate analytical techniques should be developed for forensic trace fiber analysis. Additionally, degradation associated with environmental exposures could influence comparative analysis. For example, a long time exposure to outdoor weathering could cause photodegradation of dyed fibers. Hence, the objective of this study is to develop analytical methods that can be used to detect and characterize organic dyes present in trace textile fibers with minimum sample consumption, and to understand the photodegradation process of a widely used disperse dye (C.I. Disperse Red 1) for polyester during outdoor weathering. Time-of-flight secondary ion mass spectrometry (TOF-SIMS) was successfully employed to detect trace amount of C.I. Acid Blue 25 and C.I. Disperse Red 1, by analyzing fiber cross sections of thickness 500 nm~700 nm. High resolution images demonstrating dye distribution and concentration were obtained. Additionally, operation conditions for an innovative sample preparation platform, automated microfluidic extraction device, were optimized to extract organic dyes with high efficiency to avoid the risk of contamination during sample preparation. With automated extraction, trace fibers (~2-3 mm) were successfully extracted within less than 10 min using around 9 µL solvent. Concentrated dye extracts from millimeter-length-threads and single fibers were collected and analyzed by subsequent high performance liquid chromatography separation followed by mass spectrometry. Single fibers (<5 mm length) containing 1% on- weight-of fiber (owf) were successfully detected. For comparative analysis, the most efficient and rapid method is to compare the unknown dyes to reference standards. In this aspect of the project, dye standards collected from different manufacturers were analyzed using a high performance liquid chromatography-photodiode array detection-electrospray ionization-quadrupole time of flight mass spectrometer (HPLC-DAD-ESI-QTOF-MS). Information regarding retention time, UV- vis absorption and mass spectra of the standards was recorded in a dye database for forensic purposes. For example, C.I. Direct Blue 106 contained two main components having retention times at 4.020 min and 4.353 min in HPLC-DAD chromatograms, and both components had an absorption maximum at 635 nm, and the doubly charged ions were identified as characteristic ions with a mass-to charge ratio (m/z) at 346.9890. Finally, a preilimanry photodegradation study of C.I. Disperse Red 1 on polyester by using tandem mass spectrometric analysis is presented. Three major degradation products were characterized by targeted collision-activated dissociation and the photofading pathway was established. In this regard, the predominant product (E)-N-ethyl-4-((4-nitrophenyl) diacetyl) aniline was produced rapidly and then was converted to (E)-4-((4-nitrophenyl) diazenyl) aniline. The photodegradation process was compared with that obtained in solution. © Copyright 2015 Min Li All Rights Reserved Forensic Analysis of Organic Dyes on Trace Fibers and Their Photodegradation by Min Li A dissertation submitted to the Graduate Faculty of North Carolina State University in partial fulfillment of the requirements for the Degree of Doctor of Philosophy Fiber and Polymer Science Raleigh, North Carolina 2016 APPROVED BY: ___________________________ ___________________________ David Hinks Nelson R. Vinueza Co-Chair of Advisory Committee Co-Chair of Advisory Committee ____________________________ ___________________________ Harold S. Freeman Ahmed El-Shafei _____________________________ Peter. Bloomfield BIOGRAPHY Min Li was born in Taiyuan, Shanxi, China. After completion of her high school education in 2006, she attended Beijing Institute of Fashion Technology, where she received two Bachelor Degrees of Engineering, one in Textile Chemistry and the other one in Fashion Design. Then she joined Novozymes. Inc. Beijing, China, where she worked as a lab assistant for textile industry in the department of research development. In 2012, she got her Master’s Degree in Textile Chemistry from North Carolina State University, and in the same year, she was awarded first place honors in the Herman and Myrtle Goldstein Student Paper Competition at the American Association of Textile Chemists and Colorists International Conference held in Charlotte, North Carolina for her paper entitled “An Environmentally Benign Approach to Cotton Preparation: One Bath Enzymatic Desizing, Scouring and Activated Bleaching.” In 2012 she continued her studies by pursuing a Ph.D. Degree in Fiber and Polymer Science (FPS). Her research focused on forensic analysis of dyed fibers, as well as the photodegradation of an important disperse dye under the guidance of Dr. David Hinks, Dr. Nelson R. Vinueza and Dr. Harold S. Freeman. ii ACKNOWLEDGMENTS My deep gratitude goes first to my advisors Dr. David Hinks and Dr. Nelson R. Vinueza, who expertly guided me through my graduate education and who shared the excitement of research and discovery. I would like to thank both of you for offering me the opportunity to pursue the doctoral degree in your research team and guiding me to grow as a research scientist. Your enthusiasm toward research has deeply inspired me to learn and grow. I would also like to thank my committee members, Dr. Harold S. Freeman, Dr. Ahmed El- Shafei, and Dr. Peter Bloomfield, for being my committee members and guiding my research. All of you provided your brilliant comments and suggestions during my research. Dr. Freeman offered me tremendous help in the research about photodegradation, and his wisdom, kindness, and enthusiasm toward research deeply influenced me. Dr. Peter Bloomfield, who is always nice, patient and ready to help, helped me in statistical data analysis and modeling. Grateful thanks are expressed to Elaine (Chuanzhen) Zhou, and everyone in AIF at NC State University. Elaine taught me about the concept and operation of Time-of-flight Secondary ion mass spectrometry, and offered me great suggestions on my research and personal life. I would thank Mr. Roberto Garcia, who offered training on cryomicrotoming and XRD. I thank Ms. Judy Elson, for her tremendous help with dye collection, microscopy training, weathering test and her patience and kindness. I would also thank Dr. Malgorzata Szymczyk for her guidance and help with the dye synthesis. I also thank everyone in my two research teams: Guan Wang, Nanshan Zhang, Sha Fu and Xiuzhu Fei in Dr. Hinks’ group, who are always supportive and helpful with my research. I iii thank Yufei Chen, Kelsey Boes, Emily Lichtenberger, and Nadia Sultana, who consistently offered help with my research and study. I really enjoyed working with them and learning from them. Finally, and most importantly, I am grateful to my family and friends, for their love, support and encouragement throughout my life. iv TABLE OF CONTENTS LIST OF TABLES .................................................................................................................. x LIST OF FIGURES .............................................................................................................. xii LIST OF ABBREVATIONS ............................................................................................. xxiii Chapter 1 Introduction........................................................................................................... 1 1.1. Motivation .................................................................................................................. 1 1.2. Literature Review ....................................................................................................... 4 1.2.1. Introduction to organic dyes ............................................................................... 4 1.2.2. Photodegradation of dyes .................................................................................. 16 1.2.3. Forensic fiber examination ............................................................................... 26 1.2.4. Analytical techniques for trace dye analysis ..................................................... 28 1.3. Instrumentation......................................................................................................... 44 1.4. Reference .................................................................................................................. 46 Chapter 2 Microfluidic System for Automated Dye Molecule Extraction and Detection and Characterization ............................................................................................................ 57 2.1. Preliminary study on dye extraction at conventional scale ...................................... 58 2.1.1. Dyes and chemicals........................................................................................... 58 2.1.2. Sample
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