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Emulsion Polymerization of Ethylene‑Vinyl Acetate‑Branched Vinyl Ester Using a Pressure Reactor System

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Emulsion Polymerization of Ethylene‑Vinyl Acetate‑Branched Vinyl Ester Using a Pressure Reactor System This document is downloaded from DR‑NTU (https://dr.ntu.edu.sg) Nanyang Technological University, Singapore. Emulsion polymerization of ethylene‑vinyl acetate‑branched vinyl ester using a pressure reactor system Tan, Chee Boon 2005 Tan, C. B. (2005). Emulsion polymerization of ethylene‑vinyl acetate‑branched vinyl ester using a pressure reactor system. Master’s thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/6433 https://doi.org/10.32657/10356/6433 Nanyang Technological University Downloaded on 02 Oct 2021 13:42:12 SGT ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library EMULSION POLYMERIZATION OF ETHYLENE-VINYL ACETATE-BRANCHED VINYL ESTER USING A PRESSURE REACTOR SYSTEM TAN CHEE BOON SCHOOL OF MECHANICAL AND AEROSPACE ENGINEERING NANYANG TECHNOLOGICAL UNIVERSITY 2005 ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Emulsion Polymerization of Ethylene-Vinyl acetate-Branched Vinyl Ester Using a Pressure Reactor System Tan Chee Boon School of Mechanical & Aerospace Engineering A thesis submitted to the Nanyang Technological University in fulfilment of the requirement for the degree of Master of Engineering 2005 ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Acknowledgement This research project is made possible through the efforts and support of numerous people whom I am greatly indebted to. Firstly, I would like to express my gratitude to Professor Michael Tam Kam Chiu for advice, guidance, encouragement and support during the course of this study. I also thank my co-workers and friends in The Dow Chemical Company (formerly Union Carbide Corp.), in particular, Dr. Richard Jenkins, Dr. David Bassett and Dr. Kostas Avramidis who have worked on the BEEVA project for their support and encouragement. I would also like to thank the Dow Chemical Company for its financial support. I am also grateful to Prof. Gan Leong Huat for his support in the NMR work and the discussion on the project. I thank all friends and staffs in Materials Laboratory, particularly Dai Sheng, Wang Chang, Maureen, Lee Kia Li and Ang Moh Sing for their hospitality, support and assistance. Finally, I express my gratitude to my wife Vivian for both her physical and spiritual support and encouragement. i ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Table of Contents Acknowledgement i Table of Contents ii List of Figures v List of Tables viii Abstract ix CHAPTER 1 INTRODUCTION 1.1 Overview 1 1.2 Motivation and objectives for this study 2 CHAPTER 2 LITERATURE REVIEW 2.1 Relevance and motivations 4 2.2 Historical background of VAE pressure Latex 8 2.3 Review of patent literature on ethylene-based pressure latex 10 2.4 Typical monomer compositions used in pressure latexes 24 2.5 Plasticization of vinyl acetate 24 2.6 Comparison of ethylene vs. acrylates as co-monomer for vinyl acetate 32 2.7 Pressure emulsion polymerization techniques 35 2.8 Aspects of branched vinyl esters in vinyl latex polymerization 44 2.9 Physical properties of ethylene-based latex and analytical methods used 54 ii ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library CHAPTER 3 EXPERIMENTAL METHODS AND MATERIALS 3.1 Preparation of BEEVA latexes 61 3.1.1 Model BEEVA latexes 61 3.1.2 Materials used for synthesis of BEEVA latexes 64 3.1.3 Recipe for model BEEVA latexes 65 3.2 Preparation of samples 68 3.3 Rheological measurements 69 3.4 Contact angle measurements 69 3.5 Glass transition temperature measurements 70 3.6 Nuclear magnetic resonance (NMR) spectra measurements 70 3.7 Zeta potential and particle size measurements 71 CHAPTER 4 DESIGN OF PRESSURE REACTOR SYSTEM 4.1 Design of pressure polymerization hardware 72 4.1.1 Pressure vessel 74 4.1.2 Agitator 78 4.1.3 Feed tanks and pumps 80 4.1.4 Haskel pump 81 4.1.5 Temperature control 82 4.1.6 Research motor valves 84 4.1.7 Monomer preparation system 85 4.2 Safety features 86 4.2.1 Safety devices 86 iii ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library 4.2.2 Effluent handling system 87 CHAPTER 5 PHYSICAL PROPERTIES OF LATEXES 5.1 Introduction 89 5.2 Rheological properties 90 5.3 Determination of ethylene weight percentage using proton NMR 96 5.4 Glass transition temperature 108 5.5 Contact angle 112 5.6 Zeta potential and particle size 115 CHAPTER 6 CONCLUSIONS AND RECOMMENDATIONS 6.1 Conclusions 119 6.1.1 The design of a new pressure reactor system 119 6.1.2 The preparation of model BEEVA latexes 121 6.1.3 The physical properties of model BEEVA latexes 121 6.2 Recommendations 123 REFERENCES 125 APPENDIX: Standard Operating Procedures 130 iv ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library List of Figures Figure 2.1 Simplified diagram of the raw material chain from petroleum to monomer Figure 2.2 Vinyl Acetate-Butyl Acrylate and Vinyl Acetate-Ethylene Copolymers containing 25 mole % Acrylate and Ethylene, respectively. Figure 2.3 Mass Transfer with Chemical Reaction in the BEEVA Reactor Figure 2.4 Schematic of the DISPERSIMAX Agitator used in BEEVA Polymerizations Figure 2.5 Structure of Vinyl neo-Decanoate Figure 2.6 The generic structure of branched vinyl ester Figure 2.7 Structure of BEEVA polymer Figure 2.8 Description of contact angle measurement Figure 3.1 Ratio of Neo monomer to vinyl acetate in weight% and in mole ratio Figure 4.1 Overall process flow sheet Figure 4.2 The 5-gallon reactor assembly Figure 4.3 Top view of reactor cover Figure 4.4 Impellers Figure 4.5 Feed tanks and pumps Figure 4.6 Haskel pump and transfer of ethylene. Figure 4.7 Temperature control Figure 4.8 Research motor valves v ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Figure 4.9 Monomer preparation system Figure 4.10 Safety features Figure 4.11 Effluent handling system Figure 5.1 Shear viscosity versus shear rate of different polymer concentrations (wt%) of: (a) Neo-0-500; (b) Neo10-10-500; (c) Neo10-20-500; (d) Neo10-10-750; and (e) Neo9-10-500 Figure 5.2 Plot of viscosity for varying ethylene pressure of Neo10 at different polymer solution concentration and fixed Neo10 content Figure 5.3 Plot of viscosity for varying amounts of Neo10 at different polymer solution concentration and fixed pressure of 500 psig Figure 5.4 Plot of viscosity for varying Neo monomer type at different polymer solution concentration and fixed pressure of 500 psig Figure 5.5 Location of protons for vinyl acetate and branched vinyl ester Figure 5.6 Isomers of Veova 9 Figure 5.7 Proton NMR spectra of: (a) Neo-0-500; (b) Neo10-10-500; (c) Neo10-20- 500; (d) Neo10-10-750; (e) Neo9-10-500 and (f) Neo10-10-atm Figure 5.8 Amount of ethylene (wt%) versus ethylene pressure at fixed Neo10 amount of 10% by weight to vinyl acetate Figure 5.9 Amount of ethylene (wt%) versus amount of Neo10 at fixed pressure of 500 psig Figure 5.10 Amount of ethylene versus Neo type (9, 10 and 11) at fixed amount by weight and fixed ethylene pressure Figure 5.11 DSC thermograms for varying ethylene pressure at fixed Neo10 content vi ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Figure 5.12 DSC thermograms for varying Neo10 amount at fixed ethylene pressure Figure 5.13 Glass transition temperatures versus ethylene pressure at fixed Neo10 amount (10 wt% to vinyl acetate) Figure 5.14 Glass transition temperatures versus amount of Neo10 (by wt% to vinyl acetate) at fixed pressure of 500 psig Figure 5.15 Plot of contact angle against amount of Neo10 (by wt% to vinyl acetate) at fixed pressure of 500 psig Figure 5.16 Plot of contact angle against ethylene pressure at fixed Neo10 amount of 10 wt% to vinyl acetate Figure 5.17 Zeta potential versus pH of Neo10-10-atm and Neo10-10-500 Figure 5.18 Particle diameter versus pH of Neo10-10-atm and Neo10-10-500 Figure 5.19 Zeta potential versus pH for varying Neo monomer types Figure A.1 Recovery of product vii ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library List of Tables Table 2.1 Summary of patents reviewed as categorized by invention claims of composition, process and application Table 2.2 Glass Transition Temperatures of Selective Monomers Table 2.3 Glass Transition Temperatures, Formula and Total Mass of Vinyl Ester Monomers Table 2.4 Water Solubility of Monomers at 20°C Table 2.5 Calculated monomer reactivity ratios for copolymerization with vinyl Acetate (m1) Table 3.1 Ratio of Neo monomer to vinyl acetate in weight % and in mole ratio. Table 3.2 Recipe for BEEVA latex Neo10-10-500 Table 4.1 Specifications of pressure vessel Table 5.1 The average MW of copolymers used in the NMR calculations Table 5.2 Ethylene (wt%) in the BEEVA polymers Table 5.3 Glass transition temperature of BEEVA polymers Table 5.4 Contact angle of BEEVA polymer viii ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library Abstract A new pressure reactor system was designed to synthesize a novel branched ester- ethylene-vinyl acetate (BEEVA) emulsion polymer.
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