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Development of Novel Cycloaliphatic Siloxanes for Thermal

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Development of Novel Cycloaliphatic Siloxanes for Thermal DEVELOPMENT OF NOVEL CYCLOALIPHATIC SILOXANES FOR THERMAL AND UV-CURABLE APPLICATIONS A Dissertation Presented to The Graduate Faculty of the University of Akron In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Ruby Chakraborty May, 2008 DEVELOPMENT OF NOVEL CYCLOALIPHATIC SILOXANES FOR THERMAL AND UV-CURABLE APPLICATIONS Ruby Chakraborty Dissertation Approved: Accepted: _____________________________ ______________________________ Advisor Department Chair Dr. Mark D. Soucek Dr. Sadhan C. Jana ______________________________ ______________________________ Committee Member Dean of the College Dr. Sadhan C. Jana Dr. Stephen Cheng ______________________________ ______________________________ Committee Member Dean of the Graduate School Dr. Erol Sancaktar Dr. George R. Newkome ______________________________ ______________________________ Committee Member Date Dr. George G. Chase ______________________________ Committee Member Dr. Chrys Wesdemiotis ii ABSTRACT Siloxanes have been extensively used as additives to modulate surface properties such as surface tension, hydrophobicity/hydrophobicity, and adhesion, etc. Although, polydimethyl -siloxane and polydiphenylsiloxane are the most commonly used siloxanes, the properties are at extremes in terms of glass transition temperature and flexibility. It is proposed that the ability to control the properties in between the these extremes can be provided by cycloaliphatic substitutions at the siloxane backbone. It is expected that this substitution might work due to the intermediate backbone rigidity. In order to achieve the above objectives, a synthetic route was developed to prepare cycloaliphatic (cyclopentane and cyclohexane) silane monomers followed by subsequent polymerization and functionalizations to obtain glycidyl epoxy, aliphatic amine and methacrylate telechelic siloxanes. The siloxanes were either thermally or UV- cured depending on end functionalizations. Chemical characterization of monomers, oligomers and polymers were performed using 1H, 13C, 29Si-NMR, FT-IR and GPC. The curing kinetics of photo-induced reactions were investigated through photo-differential scanning calorimetry (PDSC). The oxygen permeability, mechanical, coatings, and release properties of siloxanes were studied as a function of the backbone substitutions. The mechanical, coatings and released properties of cycloaliphatic siloxanes improved with respect to polydimethylsiloxanes. The thermal analysis of the cured films were carried out using differential scanning calorimetry (DSC). Viscoelastic properties of the iii cured siloxanes due to the variation of substitution at the siloxane backbone were measured using dynamic mechanical thermal analysis (DMTA). The cycloaliphatic substituted siloxanes showed an increased glass transition temperature and permeability but reduced crosslink density, conversion, and rate of curing with respect to polydimethylsiloxanes. Hybrids of siloxanes were prepared with linseed oil based alkyds to study the effect of variation of alkyd oil lengths and cycloaliphatic substitutions on siloxane backbone. The oil length of an alkyd resin is defined as the number of grams of oil used to produce 100 grams of resin. Three linseed oil based alkyds representing long, medium, and short oil lengths were grafted with siloxanes substituted with methyl, cyclopentyl, and cyclohexyl groups. The reaction was monitored through FTIR and 1H-NMR. The hybrids were formulated with standard drier package and thermally cured for detailed film characterization. Improvement in crosslink density, flexibility, and reverse impact resistance were found as function of oil length. However, tensile modulus, elongation, glass transition temperature, drying time and fracture toughness decreased with increase in oil length. For hybrids, the cycloaliphatic substituents at the siloxane backbone showed enhanced mechanical and coating properties as compared to hybrids with polydimethylsiloxanes. Random and block copolymer of polydimethylsiloxanes with polydicycloaliphatic- siloxanes were synthesized and compared with homopolymers of polydicycloaliphatic siloxanes. The chemical characterization of the copolymers and homopolymers were carried out through 1H, 13C, 29Si-NMR, and FT-IR. The glass transition temperatures (Tg) of the synthesized polymers were obtained through DSC and iv advanced rheometric expansion system (ARES). The Tg of random copolymers were found to be higher than the corresponding block copolymers. There was very small difference in Tg between cycloaliphaticsiloxanes homopolymers and corresponding random copolymers. From the above results, it can be inferred that the cycloaliphatic substitutions at the siloxane backbone can be used as a means to obtain properties intermediate to polydimethyl- and polydiphenyl siloxanes. v DEDICATION To my parents for their exceptional love and support vi ACKNOWLEDGEMEMNTS At this juncture of submitting my thesis, I would like to express my sincere appreciation to people who have made this possible. First of all, I would like to express my sincere gratitude towards my advisor Dr. Mark Soucek, for his exceptional guidance and support through out my stay at Polymer Engineering. My stay in this group has imparted in me the much needed multi tasking abilities and networking skills. Sincere thanks are due to my dissertation committee members who have taken time out of their hectic schedule to help me with this research work. I would like to express my special thanks to Dr. Jana, if it were not for him, I would not have landed in Akron. I would like to thank Dr. Venkat Dudipala for his help in setting up NMR experiments and Sham for helping with rheological measurement. Sincere thanks belong to Dr. Swain and Dr. Thatte for their valuable suggestions during this work. I would like to thank my group mates and friends Dr. Dworak, Dr. Nebioglu, Dr. Uma, Mayela, Elif, Serkan, Kosin, Jamie, Dr. Gua, Neel and Veronica for providing a healthy and happy environment to do research and have fun. Finally I would like to thank all faculty and staff of Polymer Engineering for directly or indirectly helping me in achieving this goal. vii TABLE OF CONTENTS Page LIST OF TABLES………………………………………………………………………xiii LIST OF FIGURES ……………………………………………………………………...xv CHAPTER I. INTRODUCTION ……………………………………………………………………1 II. BACKGROUND………………………………………………………………………5 2.1 An overview on polysiloxanes …………………………………………………..5 2.2 Nomenclature of polysiloxanes …………………………………………………7 2.3 Properties………………………………………………………………………...8 2.4 Monomer synthesis …………………………………………………………….12 2.4.1 Hydrosilation…………………………………………………………...14 2.5 Synthesis of polyorganosiloxanes ……………………………………………...17 2.5.1 Mechanism for polysiloxane synthesis ………………………………...17 2.5.1.1 Equilibrium polymerization ………………………………….19 2.5.1.2 Anionic polymerization………………………………………21 2.5.1.3 Cationic polymerization ……………………………………...24 2.5.2 Structure of synthesized polysiloxanes ………………………………...27 viii 2.5.2.1 Linear polysiloxanes …………………………………………27 2.5.2.2 Block and graft polysiloxanes ………………………………29 2.5.2.3 Side group modified polysiloxanes …………………………33 2.5.2.4 Polyorganosilesquioxanes ……………………………………34 2.6 Backbone substitution and functionalization of polysiloxanes ………………...36 2.7 Hybrids of siloxanes with other polymers…...…………………………………39 2.8 Curing of siloxanes …………………………………………………………….41 2.8.1 Radiation curing ………………………………………………………42 2.8.1.1 UV initiated cross-linking ……………………………………42 2.8.1.1.1 Free radical initiated UV-curing …………………44 2.8.1.1.2 Cationic UV-curing ……………………………45 2.8.1.2 Electron beam (EB) curing…………………………………...47 2.8.2 Thermally induced cross-linking……………………………………….47 2.8.3 Moisture induced cross-linking………………………………………...50 2.8.4 Addition Curing………………………………………………………...51 III. EXPERIMENTAL …………………………………………………………………...53 3.1 Materials ………………………………………………………………………53 3.2 Synthesis ………………………………………………………………………54 3.2.1 Synthesis of dicycloaliphatic dichlorosilane …………………………...55 3.2.2 Synthesis of cyclic oligomer of polydicycloaliphaticsiloxane …………55 3.2.3 Activation of ion exchange resin……………………………………….56 3.2.4 Synthesis of hydride terminated polydimethylsiloxane. ……………….57 3.2.5 Synthesis of hydride terminated polydicycloaliphaticsiloxane ………..57 ix 3.2.6 Synthesis of glycidyl epoxide terminated PDMS, PDPS, and PDHS ………………………………………………………58 3.2.7 Epoxy equivalent weight determination (EEW) ……………………...59 3.2.8 Synthesis of t-butoxycarbonyl (BOC) protected allyamine ……………60 3.2.9 Synthesis of amine terminated PDMS, PDPS, and PDHS……………..60 3.2.10 Synthesis of methacrylate terminated PDMS, PDPS, and PDHS ……...62 3.2.11 Synthesis of linseed oil based short oil, medium oil and long oil alkyds…………………………………………………………………...63 3.2.12 Synthesis of Block Copolymer of PDMS with PDPS PDMS-block-PDPS) and PDHS(PDMS-block-PDHS) ………………64 3.2.13 Synthesis of homopolymers of PDPS and PDHS………………………65 3.2.14 Synthesis of random copolymer of PDMS with PDPS (PDMS-ran-PDPS) and PDHS (PDMS-ran-PDHS) …………………..66 3.3 Characterization………………………………………………………………...67 3.3.1 Proton, Carbon and Silicon Nuclear Magnetic Resonance (1H NMR, 13C-NMR, and 29Si NMR) ………………………………….67 3.3.2 Fourier Transform Infrared Spectroscopy (FT-IR) …………………….67 3.3.3 Gel Permeation Chromatography (GPC) ………………………………67 3.3.4 Differential Scanning Calorimetry (DSC)……………………………...68 3.3.5 Photo-Differential Scanning Calorimetry (PDSC)……………………..68 3.3.6 Dynamic Mechanical Thermal Analysis (DMTA) …………………….68 3.3.7 Oxygen permeation analysis …………………………………………..69 3.3.8 X-Ray
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