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Kuan-Chen Huang Master Thesis

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Kuan-Chen Huang Master Thesis @ 2021 Kuan-Chen Huang ALL RIGHTS RESERVED STUDY THE APPLICATION OF NON-ISOCYANATE APPROACH IN POLYURETHANES AND DIOLS A Thesis Presented to The Graduate Faculty of The University of Akron In Partial Fulfillment of the Requirements for the Degree Master of Science Kuan-Chen Huang May, 2021 STUDY THE APPLICATION OF NON-ISOCYANATE APPROACH IN POLYURETHANES AND DIOLS Kuan-Chen Huang Thesis Approved: Accepted: ______________________________ ___________________________ Advisor Department Chair Dr. Qixin Zhou Dr. Lu-Kwang Ju ______________________________ ___________________________ Committee Member Interim Dean of the College Dr. Zhenmeng Peng Dr. Craig Menzemer ______________________________ ___________________________ Committee Member Dean of the Graduate School Dr. Junpeng Wang Dr. Marine Saunders ___________________________ Date ii ABSTRACT Conventional polyurethanes have been widely used over the world for foams, coatings, and food packaging films. However, conventional polyurethanes are produced from isocyanates which are harmful and toxic. Recently, scientists have developed alternative processes to produce polyurethanes without using isocyanates. The most used non-isocyanate method to obtain the urethane group is by the reaction of cyclic carbonates with amines. This method becomes popular is because various cyclic carbonates and amines can be selected. The work of this thesis is the application of the non-isocyanate approach through the cyclic carbonate/amine method. In this thesis, a non-isocyanate polyurethane (NIPU) and urethane diols were developed using the non-isocyanate approach. In Chapter 3, a zinc phosphate pigmented NIPU was designed to improve the corrosion resistance of the polyurethane coating. In Chapter 4, urethane diols were produced by the non-isocyanate approach. And then, the urethane diols were crosslinked by a hexa(methoxymethyl) melamine (HMMM) crosslinker to increase the mechanical property of the coating. In Chapter 3, the NIPU was successfully synthesized from bisphenol A cyclic carbonate and fatty acid amine. Different weight percentages of zinc phosphate pigments were added to the NIPU. The corrosion resistance of the NIPU coating was investigated by electrochemical impedance spectroscopy and salt spray measurement. The corrosion resistance of the NIPU was increased by adding the zinc phosphate pigments. The NIPU iii coating with 5 wt. % zinc phosphate pigment showed the best corrosion resistance among the whole formulations. This study provides a capability for the application of NIPU in corrosion protective coatings. In Chapter 4, the urethane diols were produced by the non-isocyanate approach at room temperature without using any catalyst. Two urethane diols with different middle chains were obtained by the reaction of 1,4-diaminobutane or 1,6-diaminohexane with ethylene cyclic carbonate, respectively. Different weight percentages of HMMM crosslinker were mixed with urethane diols. The mechanical property of the coating was investigated by tensile test, adhesion test, and conical mandrel bend test. The HMMM crosslinker can react with urethane diols to form a polymer network to generate a coating film. This study provides a non-isocyanate way to produce urethane diols and successfully used them in melamine-formaldehyde coatings. The urethane diols can be further utilized for producing coatings and polymers. In general, this thesis successfully synthesized NIPU and urethane diols through a non-isocyanate approach. By further adding the NIPU with zinc phosphate pigments or crosslinking the urethane diols with HMMM crosslinkers, this thesis intends to expand the non-isocyanate method for the application in corrosion protective coatings. This work would encourage the replacement of conventional polyurethanes or urethane diols for green and environmentally friendly alternatives. iv ACKNOWLEDGEMENTS I would like to show my sincere appreciation to Dr. Qixin Zhou for her patience, motivation, research suggestion, and encouragement. Her valuable guideline helped me throughout my entire master’s study. I would also like to express my appreciation to the committee members: Dr. Peng and Dr. Wang for their comments. I also much appreciate Dr. Lingyan Li and Mr. Will Imes for their help with instrumental support. I would also like to thank all my group members, Haoran Wang, Cheng Zhang, Weixiu Zeng, and Zichen Ling. Finally, I would like to express special thanks to my parents, who have always been supporting me in my master’s study. v TABLE OF CONTENTS LIST OF FIGURES ..................................................................................................... ix LIST OF TABLES ....................................................................................................... xi CHAPTER I INTRODUCTION ....................................................................................................... 1 1.1 Overview of Work ................................................................................................ 1 1.2 Research Objectives .............................................................................................. 2 CHAPTER II BACKGROUND ......................................................................................................... 3 2.1 Organic Coating .................................................................................................... 3 2.2 Polyurethane Binder ............................................................................................. 3 2.3 Melamine Formaldehyde Binder .......................................................................... 5 2.4 Characterization .................................................................................................... 7 2.4.1 Electrochemical Impedance Spectroscopy (EIS) .................................... 7 2.4.2 Fourier Transform Infrared Spectroscopy (FTIR) .................................. 8 2.4.3 Salt Spray Test ........................................................................................ 8 2.4.4 Tape Adhesion Test ................................................................................ 9 2.4.5 Flexibility Test ........................................................................................ 10 2.4.6 Tensile Test ............................................................................................. 11 CHAPTER III vi ANTI-CORROSION NON-ISOCYANATE POLYURETHANE WITH ZINC PHOSPHATE PIGMENT COATINGS ...................................................................... 12 3.1 Introduction ........................................................................................................... 12 3.2 Experimental ......................................................................................................... 13 3.2.1 Material ................................................................................................... 13 3.2.2 Synthesis of BPA Cyclic Carbonate ....................................................... 14 3.2.3 Synthesis of Amine-terminated NIPU .................................................... 14 3.2.4 Preparation of NIPU Coatings with Pigments ........................................ 14 3.2.5 Instrumentation ....................................................................................... 16 3.3 Results and Discussion ......................................................................................... 16 3.3.1 Structural Characterization of BPA Cyclic Carbonate ........................... 16 3.3.2 Structural Characterization of Amine-terminated NIPU ........................ 20 3.3.3 Anti-corrosion Performance Evaluation: EIS ......................................... 20 3.3.4 Anti-corrosion Performance Evaluation: Salt Spray ............................... 25 3.4 Conclusion ............................................................................................................ 27 CHAPTER IV URETHANE DIOLS VIA NON-ISOCYANATE PROCESS AND ITS CHARACTERIZATION IN THE COATING ............................................................ 28 4.1 Introduction ........................................................................................................... 28 4.2 Experimental ......................................................................................................... 30 4.2.1 Material ................................................................................................... 30 4.2.2 Synthesis of Urethane Groups Diols ....................................................... 30 4.2.3 Preparation of Films ................................................................................ 31 4.2.4 Instrumentation ....................................................................................... 33 vii 4.3 Results and Discussion ......................................................................................... 34 4.3.1 Structural Characterization of Urethane Diols ........................................ 34 4.3.2 Films Properties ...................................................................................... 37 4.4 Conclusion ............................................................................................................ 42 CHAPTER V SUMMARY ................................................................................................................. 44 REFERENCES ............................................................................................................ 45 viii LIST OF FIGURES Figure 2. 1 The reaction of isocyanates with alcohols
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