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Influence of Electrostatic Interactions and Hydrogen Bonding on the Thermal and Mechanical Properties of Step-Growth Polymers

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Influence of Electrostatic Interactions and Hydrogen Bonding on the Thermal and Mechanical Properties of Step-Growth Polymers Influence of Electrostatic Interactions and Hydrogen Bonding on the Thermal and Mechanical Properties of Step-Growth Polymers Sharlene R. Williams Dissertation submitted to the faculty of the Virginia Polytechnic Institute and State University in partial fulfillment of the requirements for the degree of Doctor of Philosophy In Chemistry Timothy E. Long, Chair Thomas C. Ward, Member S. Richard Turner, Member Maren Roman, Member Susan E. Duncan, Member October 21, 2008 Blacksburg, Virginia Keywords: Hydrogen bonding, Electrostatic Interactions, Michael Addition, Polyurethane, Ionene, Thermomechanical Behavior Influence of Electrostatic Interactions and Hydrogen Bonding on the Thermal and Mechanical Properties of Step-Growth Polymers Sharlene R. Williams ABSTRACT Current research efforts have focused on the synthesis of novel, segmented, cross-linked networks and thermoplastics for emerging technologies. Tailoring macromolecular structures for improved mechanical performance can be accomplished through a variety of synthetic strategies using step-growth polymerization. The synthesis and characterization of novel Michael addition networks, ionene families, and ion-containing polyurethanes are described, with the underlying theme of fundamentally investigating the structure-property relationships of novel, segmented macromolecular architectures. In addition, it was discovered that both covalent and electrostatic crosslinking play an important role in the mechanical properties of all types of polymers described herein. Novel cross-linked networks were synthesized using quantitative base-catalyzed Michael chemistry with acetoacetate and acrylate functionalities. These novel synthetic strategies offer unique thermo-mechanical performance due to the formation of a multiphase morphology. In order to fundamentally elucidate the factors that influence the kinetics of the Michael addition reaction a detailed analyses of model compounds were conducted in the presence of an in-situ IR spectrometer to optimize reaction conditions using statistical design of experiments. Networks were then prepared based on these optimized conditions. The mechanical performance was evaluated as a function of molecular weight between crosslink points. Furthermore, the incorporation of hydrogen bonding within the monomer structure enhanced mechanical performance. The changes in morphological, thermal, and mechanical properties evaluated using dynamic mechanical analysis (DMA) and tensile behavior are described. In addition, the use of preformed urethane segments provides a safer method for incorporating hydrogen bonding functional groups into macromolecules. In order to compare the thermomechanical and morphological properties of ion- containing polyurethanes to non-charged polyurethanes, poly(tetramethylene oxide)-based polyurethanes containing either a novel phosphonium diol or 1,4-butanediol chain extenders were prepared using a prepolymer method. The novel phosphonium polyurethane was more crystalline, and it was presumed that hydrogen bonding in the non-charged polyurethane restricted polymer mobility, and reduced PTMO crystallinity, and hydrogen bonding interactions were significantly reduced due to the presence of phosphonium cations. These results correlated well with mechanical property analysis. The phase separation and ionic aggregation were demonstrated via wide-angle X-ray scattering, small-angle X-ray scattering, scanning transmission electron microscopy, and energy-dispersive X-ray spectroscopy during STEM imaging, as described herein. In addition, a novel polyurethane containing imidazolium cations in the hard segment was synthesized and behaved very similarly to the phosphonium cation- containing polyurethane. Ammonium ionenes, which contain quaternary nitrogen in the macromolecular repeating unit, have many potential uses in biomedical applications. They offer interesting coulombic properties, and the charge density is easily controlled through synthetic design. This property makes ionenes ideal polyelectrolyte models to investigate the influence of ionic aggregation on iii many physical properties. Ammonium ionenes were prepared via the Menshutkin reaction from 1,12-dibromododecane and 1,12-bis(N,N-dimethylamino)dodecane. The absolute molecular weights were determined for the first time using an on-line multi-angle laser light scattering (MALLS) in aqueous size exclusion chromatography (SEC). Tensile testing and DMA were used to establish structure-property relationships between molecular weight and mechanical properties for a series of 12,12-ammonium ionenes. Furthermore, degradation studies in the presence of base support the possibility for water-soluble coatings with excellent mechanical durability that are amenable to triggered depolymerization. A novel synthetic strategy was utilized to prepare chain extended 12,12-ammonium ionenes containing cinnamate functional groups. In the presence of UV light, the polymers chain extended, and the resulting ionenes possessed enhanced thermomechanical properties and increased molecular weight. In addition, the novel synthesis of imidazolium ionenes was demonstrated, and the charge density was tuned for appropriate applications using either low molecular weight segments or oligomeric precursors. The change in charge density had a profound role in imidazolium ionene thermal and mechanical behavior. iv ACKNOWLEDGEMENTS I would like to thank my advisor, Tim Long, for his guidance throughout my graduate career. I thank all of my committee members for their interest and helpful suggestions concerning my research: Prof. Tom Ward, Prof. Richard Turner, Prof. Susan Duncan, and Prof. Maren Roman. My committee was also helpful with giving advice, especially Prof. Tom Ward. Various staff members made my stay at Virginia Tech a little easier, including Vicki Long, Millie Ryan, Laurie Good, Tammy Jo Hiner, Mary Jane Smith, Mary Dean Coleman, JaeHee Hong, and Jan McGinty, and I thank you for your assistance over the years. Filling the pages of this thesis would not have been possible without my collaborators, including Dr. Kevin Miller of Rohm and Haas, Prof. Craig Thatcher and Ben Lepene of Virginia-Maryland Regional College of Veterinary Medicine, Dr. Clay Bunyard of Kimberly-Clark, Prof. Karen Winey, Sunny Wang, and David Salas-de la Cruz of University of Pennsylvania. Working with a variety of people from different backgrounds made the research projects more interesting and gave the results greater depth than I could have ever accomplished alone. In addition, I acknowledge the funding sources for my research, including MILES IGERT, MAP MURI, ILEAD MURI, Rohm and Haas, and Kimberly-Clark. I would especially like to thank fellow group members, present and past, for their camaraderie and research assistance over the years, including Tomonori, Kalpana, Emily, Shijing, Serkan, Gozde, Qin, John, Ann, Matt M., Erika, Takeo, Funda, Bill, Andy, Matthew, Matt H., Mana, Akshay, Sean, Renlong, Eva, Steve, Matt G., and Tianyu. I appreciate everything that Afia and Casey helped me with during the beginning of graduate school, especially with making it through the first year and my first reactions. I thank Brian for help with research and friendship over the years. Rebecca made graduate school a little less painful and a lot more fun with her friendship. The assistance of my undergraduate students, especially Sophie Barta and Brian Mohns, is appreciated. My chemistry teacher at Northeastern High School, Beth Funderburg, provided inspiration to become a scientist, and I thank her for it. I also thank my professors at Wright State University, especially Prof. Eric Fossum and Prof. Kenneth Turnbull for the great experiences I had as an undergraduate researcher. I give my deepest thanks to my parents, Doug and Sharon Hopkins, for always believing in me and reminding me to do my very best. I thank v my brother Doug Jr., and his family, for providing support over the years. I also thank my entire family and friends, especially Jessica Maxson, for their support and love. Finally, I can’t imagine going though all of this without my husband, Larry. Thank you for all of your love, encouragement, and inspiration to do my best. vi Attributions • Timothy E. Long o VT Professor, graduate research advisor • Erika M. Borgerding o VT M.S., conducted aqueous SEC experiments and analyzed data • John M. Layman o VT Ph.D., conducted aqueous SEC experiments and analyzed data • Karen I. Winey o UPenn Professor, advisor to Wenqin Wang and David Salas, collaborator • Wenqin Wang o UPenn Ph.D. graduate student, conducted X-ray scattering experiments, analyzed data, and assisted with manuscript preparation and editing • Zsofia Barta o Visiting undergraduate student, assisted with synthesis and characterization of polymers • Sean M. Ramirez o VT associate research professor, synthesized a polymer and edited manuscript • David Salas o UPenn Ph.D. graduate student, conducted X-ray scattering experiments, analyzed data, and assisted with manuscript preparation and editing • Kevin M. Miller o Ph.D., Rohm and Haas, conducted experiments and assisted with manuscript preparation and editing • Brian D. Mather o VT Ph.D., assisted with data analysis and editing of manuscript • Benjamin S. Lepene o VMRCVM Ph.D. graduate student, assisted with experiments and manuscript editing • Craig D. Thatcher o Former VMRCVM professor, advisor to Benjamin Lepene, collaborator vii Table of Contents Chapter 1 : Introduction .............................................................................................................
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