Iowa State University Capstones, Theses and Graduate Theses and Dissertations Dissertations 2014 Novel plant oil-based thermosets and polymer composites Kunwei Liu Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/etd Part of the Materials Science and Engineering Commons, and the Mechanics of Materials Commons Recommended Citation Liu, Kunwei, "Novel plant oil-based thermosets and polymer composites" (2014). Graduate Theses and Dissertations. 14213. https://lib.dr.iastate.edu/etd/14213 This Thesis is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Graduate Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. i Novel plant oil-based thermosets and polymer composites by Kunwei Liu A thesis submitted to the graduate faculty in partial fulfillment of the requirements for the degree of Master of Science Major: Materials Science and Engineering Program of Study Committee: Samy Madbouly, Co-major Professor Nicola Bowler, Co-major Professor Vinay Dayal Larry Genalo Iowa State University Ames, Iowa 2014 Copyright © Kunwei Liu, 2014. All rights reserved ii TABLE OF CONTENTS LIST OF TABLES ................................................................................................................... iv LIST OF FIGURES .................................................................................................................. v ACKNOWLEDGEMENTS ................................................................................................... viii CHAPTER 1 : GENERAL INTRODUCTION ........................................................................ 1 1.1 Thesis Organization......................................................................................................... 1 1.2 Background and Literature Review................................................................................. 2 1.2.1 The petroleum crisis and future trends of vegetable oil-based polymers ................. 2 1.2.1 Vinyl polymers derived from vegetable oils ............................................................ 5 1.3 Objectives .................................................................................................................. 14 1.4 Reference ................................................................................................................... 14 CHAPTER 2 : BIO-BASED THERMOSETTING POLYMER BASED ON SOYBEAN OIL AND EUGENOL ............................................................................................................ 19 2.1 Abstract ......................................................................................................................... 19 2.2 Introduction ................................................................................................................... 20 2.3 Experiment Details ........................................................................................................ 24 2.3.1 Materials ................................................................................................................. 24 2.3.2 Synthesis of methacrylated eugenol ....................................................................... 24 2.3.3 Free radical polymerization of AESO/ME copolymers ......................................... 25 2.3.4 Material Characterizations ...................................................................................... 26 2.4 Result and Discussion ................................................................................................... 28 2.4.1 Synthesis of AESO/ME copolymers ...................................................................... 28 2.4.2 NMR ....................................................................................................................... 30 2.4.3 Soxhlet extraction ................................................................................................... 33 2.4.4 Rheological properties ............................................................................................ 33 2.4.5 Thermal properties .................................................................................................. 36 2.4.6 Compression testing ............................................................................................... 41 iii 2.5 Conclusion ..................................................................................................................... 44 2.6 Acknowledgements ....................................................................................................... 45 2.7 References ..................................................................................................................... 45 CHAPTER 3 : BIORENEWABLE POLYMER COMPOSITES FROM TALL OIL-BASED POLYAMIDE AND LIGNIN-CELLULOSE FIBER ........................................................... 50 3.1 Abstract ......................................................................................................................... 50 3.2 Introduction ................................................................................................................... 51 3.3 Experimental Procedure ................................................................................................ 55 3.3.1 Materials ................................................................................................................. 55 3.3.2 Composite Preparation ........................................................................................... 56 3.3.3 Morphological characterization .............................................................................. 56 3.3.4 Optical Microscopy ................................................................................................ 57 3.3.5 DMA measurements ............................................................................................... 57 3.3.6 DSC measurements................................................................................................. 57 3.3.6 TGA measurements ................................................................................................ 58 3.3.7 Rheological measurements ..................................................................................... 58 3.3.8 Mechanical testing .................................................................................................. 58 3. 4 Results and Discussion ................................................................................................. 59 3.4.1 Optical microscopy and SEM ................................................................................. 59 3.4.2 Rheology ................................................................................................................. 60 3.4.3 DMA ....................................................................................................................... 63 3.4.4 DSC ........................................................................................................................ 65 3.4.5 TGA ........................................................................................................................ 66 3.4.6 Mechanical testing .................................................................................................. 70 3.4 Conclusions ................................................................................................................... 73 3.5 Acknowledgements ....................................................................................................... 73 3.6 References ..................................................................................................................... 73 CHAPTER 4: GENERAL CONCLUSION ............................................................................ 78 4.1 Summary ....................................................................................................................... 78 4.2 Recommendation for future works ................................................................................ 80 4.3 Reference ....................................................................................................................... 83 iv LIST OF TABLES Table 1-1: Chemical structures and formulas for some common fatty acids [9, 10]. ............... 7 Table 2-1: Soxhlet extraction data for all copolymers. ........................................................... 33 Table 2-2: Glass transition temperature and storage modulus at room temperature. The glass transition temperatures is obtained from the maxima the tan δ curves obtained by DMA analysis. ........................................................................................................................ 38 Table 2-3: Important thermal degradation temperature for AESO/ME copolymers. ............. 41 Table 3-1: Important degradation temperature obtained from TGA. ..................................... 69 v LISTS OF FIGURES Figure 1-1: Chemical structure of triglycerides. ....................................................................... 6 Figure 1-2: Chemical structures of styrene, divinylbenzene, soybean oil and their copolymers produced by cationic polymerization [17]. ........................................................... 9 Figure 1-3: Synthesis of soybean oil monoglyceride maleates and copolymerization with styrene