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研究生： Livy Laysandra
Livy Laysandra
論文名稱： 可自我交聯之彈性自修復高分子開發暨其應用
The Design of Self-Crosslinkable Elastic Self-Healing Polymers and Their Application
指導教授： 邱昱誠
Yu-Cheng Chiu
口試委員: 邱昱誠
Yu-Cheng Chiu
張家耀
Jia-Yaw Chang
陳良益
Liang-Yih Chen
江偉宏
Wei-Hung Chiang
康敦彥
Dun-Yen Kang
李文亞
Wen Ya Lee
學位類別： 博士
Doctor
系所名稱： 工程學院 - 化學工程系
Department of Chemical Engineering
論文出版年： 2023
畢業學年度： 112
語文別： 英文
論文頁數： 164
中文關鍵詞： 自修復 、可自交聯 、分子擴散 、氫鍵 、薄膜
外文關鍵詞： self-healing, self-cross-linkable, molecular diffusion, H-bonds, thin film
相關次數： 點閱：55  下載：0 
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    • 開發具有強大機械性質的自修復可交聯聚合物在許多應用都是一值熱門的話題，特別為達到長期及安全的服務過程可不犧牲實際應用的預期性能。然而，重大的挑戰就是如何達到機械性質與自修復效率的良好平衡，所以開發出一個快速和簡單的方法可很容宜控制機械性質與自修復性質是一個重大的需求。這裡我們提出兩種可控制機械性質與自修復性質聚合物材料的合成方法包括自由基聚合的兩親性共聚物（AP）聚（（丙烯酸正丁酯）-co-[N-（羥甲基）丙烯醯胺]）（ PBA0.8-co-PNMA0.2) 和自由基改質的順式 1,4-聚異戊二烯 (rm-PI)。
    BA柔軟的特性可增強分子網路共聚物內鏈的流動性，以協助自修復的機制，而NMA的其動態氫鍵可產生自修復和自交聯能力。此外，AP的適用性在三個不同的應用領域皆已得到進一步證實，包括發光二極體（LED）、氣體分離和抗菌複合材料。對於第一個應用，將AP 與硼摻雜石墨烯量子點 (BGQD) 結合，可製備出發紅光的奈米複合薄膜以作為白光 LED (WLED) 發射層的應用。值得注意的是，PBA0.8-co-PNMA0.2中側鏈的存在可與BGQDs的官能基產生協同效應，增強奈米複合薄膜的發光穩定性及物理性能和機械性能。在第二個應用裡，利用AP當氣體分離膜卓越地分離CO2/N2。NMA鏈段上的-OH和-NH官能基可透過氫鍵與CO2相互作用，讓AP可作為氣體分離膜對CO2/N2有優異的選擇性，其性能接近商用的PEBAX-1657膜（22.92對20.09）。重要的是，不像PEBAX-1657膜，AP獨特的自修復性質可讓在真空抽水機的高吸力下破裂的膜啟動自我修復，因此AP的高透氣性和CO2/N2的選擇性還能被維持既使已透過好幾次的分離過程。對於第三個應用，將AP與兩種商用陽離子抗菌劑（即二甲基十八烷基（3-三甲氧基甲矽烷基丙基）氯化銨（DTSACL）和葡萄糖酸氯己定（CHG））結合，製備出新型多功能聚合物複合膜（(AP/b%CHG)-接枝-a%DTSACL)作為抗菌劑。具有加強熱穩定性、疏水性、機械強度和自修復能力的複合膜，可對革蘭氏陰性菌（大腸桿菌）和革蘭氏陽性菌（金黃色葡萄球菌）表出長期優異的抗菌活性（100%），還有防污功能。
    而另，由於利用具剛性特性N-乙烯基咔唑（NVC）當p型半導體材料和具軟特性2-[[(丁基氨基)羰基]氧基]丙烯酸乙酯（BACO）當自修復材料，rm-PI表出強大的自修復性能和綜合機械性質。透過合適NVC和BACO網路組成比例，自由基改質的PI獲得優秀機械性能（拉伸應力為2.91 MPa，最大應變為1086 %，韌性為25.27 MJ m-3）、缺口不敏感、快速恢復能力且連續25次循環測試後仍保持在初始耗散能量的96%。動態氫鍵網絡和聚合物鏈的物理擴散的協同作用讓已透過致命切割後有高自主修復效率高達>90%。我們預計這些研究成果可促進可行的方法發展多功能改質順式PI，作為潛力的未來p型半導體層於有機場效電晶體（OFET）裝置。
    我們的研究深入探討了可自修復材料的簡易開發方法，並對其機械性能進行了良好的折衷，使其可適用於廣泛的應用，包括 LED 設備、氣體分離膜、抗菌劑以及其他電子元件和裝置。

    The development of self-healing cross-linkable polymers with robust mechanical properties have been being the hot topics for a lot of applications, especially for long-term and safe service processes without sacrificing the intended application performances. However, the main challenge in such process is always how to achieve a good trade-off between the mechanical properties and self-healing efficiency. In this regards, developing a facile and simple route which allows ease of controllability between the mechanical and self-healing properties is highly demanded. Here we propose two methods in fabricating polymeric materials with controllable mechanical and self-healing properties, including free-radical polymerization of amphiphilic copolymer (AP) poly((n-butyl acrylate)-co-[N-(hydroxymethyl)acrylamide]) (PBA0.8-co-PNMA0.2) and radically modified cis 1,4-polyisoprene (rm-PI).
    The former mainly utilizes n-butyl acrylate (BA) and N-(hydroxymethyl)acrylamide (NMA) segments during the fabrication of these amphiphilic copolymers to offer easy tuning of mechanical and self-healing properties. BA with its soft characteristic, bestows enhancement chain mobility within the molecular network copolymers to assist the self-healing mechanism. Meanwhile, NMA was chosen due to the dynamic hydrogen bonds that can generate self-healing and self-crosslinker capabilities. Moreover, the applicability of AP is further demonstrated in three different application fields, including light-emitting diode (LED), gas separation, and antimicrobial composites. For the first application, the AP is incorporated with boron-doped graphene quantum dots (BGQDs) to fabricate red-emitting nanocomposite films as emissive layer for white LED (WLED) applications. It is worthy to note that the presence of side chains in PBA0.8-co-PNMA0.2 can initiate synergistic effects with the functional groups of BGQDs to enhance the luminescence stability, as well as physical and mechanical properties of the nanocomposite film. In the second application, the AP is employed as gas separation membrane for CO2/N2 separation with remarkable performance. The presence of –OH and –NH functional groups on the NMA segment can also interact with CO2 via hydrogen bonding, enabling the AP to be used as gas separation membrane with superior selectivity for CO2/N2 which is close to the commercially available PEBAX-1657 membrane (22.92 vs. 20.09). Importantly, unlike PEBAX-1657 membrane, the unique self-healing properties of AP can initiate self-auto membrane repair upon fracture by the high suction force of vacuum pump, thus the high gas permeability and CO2/N2 selectivity of AP can be maintained even after numerous separation processes. For the third application, the AP is combined with two types of commercial cationic antimicrobial agents (i.e. dimethyl octadecyl (3-trimethoxysilylpropyl) ammonium chloride (DTSACL) and chlorhexidine gluconate (CHG)) to fabricate a novel multifunctional modified polymer film ((AP/b%CHG)-grafted-a%DTSACL) as antimicrobial agents. The resulting copolymer/antimicrobial compound film with enhanced thermal stability, hydrophobicity, mechanical strength and self-healing capabilities enables long-term superior antibacterial activity (100 %) against Gram-negative (Escherichia coli) and Gram-positive bacteria (Staphylococcus aureus), and antifouling function.
    On the other hand, the rm-PI exhibit robust self-healing and comprehensive mechanical performances by utilizing rigid-characteristic of N-vinyl carbazole (NVC) as p-type semiconducting material and soft-characteristic 2-[[(Butylamino)carbonyl]oxy]ethyl acrylate (BACO) as autonomous self-healable material. Through appropriate ratio content of NVC and BACO network components, the radically modified PI achieved splendid mechanical properties (tensile stress of 2.91 MPa, a maximum strain of 1086 %, and toughness of 25.27 MJ m-3), notch-insensitive, and excellent fast recoverability that remained at 96% of initial dissipated energy after continuous 25 times cycle test. The synergism between the dynamic H-bonding networks and the physical diffusion of polymer chains contributed to a high autonomic self-healing efficiency of >90% after undergoing a deadly cut. These outcomes are expected to promote a viable approach for developing multi-feature modified cis-PI that could serve as a promising modern p-type semiconducting layer for organic field effect transistor (OFET) device applications.
    Our work provides insight into the facile and simple development of self-healable materials with good compromisation over their mechanical properties usable for broad applications, including LED devices, gas separation membranes, antimicrobial agents and other electronic devices.

    Abstract i 摘要 iii Acknowledgement v Publications vii Table of Contents ix List of Figures xii List of Tables xxii Chapter 1 – Introduction 1 Chapter 2 – Research Methodology 16 2.1. Summary Experimental Planning for Each Topic in the Form of Flow Chart. 16 2.2. Chemicals and Materials 18 2.3. Characterizations 19 2.4. Experimental Procedures for Chapter III. 22 2.4.1. Synthesis of amphiphilic copolymer 22 2.4.2. Synthesis of Boron-doped-Graphene Quantum Dots (BGQDs) 23 2.4.3. Preparation of the x% (w/w)@BGQDs/AP nanocomposite film 23 2.4.4. Fabrication of WLEDs 24 2.5. Experimental Procedures for Chapter IV. 24 2.5.1. Synthesis of the APNMA and APMAA 24 2.5.2. Fabrication of the APn membranes 25 2.5.3. Mechanical tests for the APn membranes 28 2.5.4. Conventional and vacuum-assisted self-healing 28 2.5.5. Gas permeation test 29 2.6. Experimental Procedures for Chapter V 30 2.6.1. Preparation of modified polymer (AP/b%CHG-grafted-a%DTSACL) in the bulk form 30 2.6.2. Preparation of (AP/b%CHG)-grafted-a%DTSACL in film form 31 2.6.3. Antimicrobial activity of (AP/b%CHG)-grafted-a%DTSACL against E. coli and S. aureus 31 2.6.4. Antifungal assessment 33 2.7. Experimental Procedure for Chapter VI 33 2.7.1. Synthesis of rm-PI 33 Chapter 3 – Optimizing the Use of Amphiphilic Copolymers as Protective Matrix for Boron-doped Graphene Quantum Dots: One Step Advance for WLED Application 36 3.1. Research Background 36 3.2. Results and Discussion 38 3.2.1. Characterization of BGQDs 40 3.2.2. Mutually synergistic effect of BGQDs/AP to the physical, mechanical, self-healing, and self-recoverability properties of nanocomposites. 43 3.2.3. x% (w/w)@BGQDs/AP nanocomposite film for LED Devices 51 Chapter 4 – Vacuum-Assisted Self-Healing Amphiphilic Copolymer Membranes for Gas Separation 55 4.1. Research Background 55 4.2. Results and Discussion 61 4.2.1. Characterization of APn 61 4.2.2. Adjustable physical and mechanical properties of APn based on thermal cross-linkable study 63 4.2.3. Conventional self-healing and self-recoverability properties 66 4.2.4. Vacuum-assisted self-healing 71 4.2.5. Membrane gas separation 73 Chapter 5 – Elastic and Self-Healing Copolymer Coatings with Antimicrobial Function. 80 5.1. Research Background 80 5.2. Results and Discussion 83 5.2.1. Optimized mechanical, self-recovery, and self-healing properties of the (AP/b%CHG)-grafted-a%DTSACL based on the synergistic effects of hydrogen bond interactions 86 5.2.2. Self-healing ability of transparent AP and modified polymers in micro-thick films 97 5.2.3. Effect of DTSACL and CHG on the hydrophobic properties of the modified polymer films 99 5.2.4. Antimicrobial evaluations 101 Chapter 6 – Radically Modified PI Toward a Multifunctional Rubber Moiety with Stretchable, Self-Healable, and Recyclable Properties 106 6.1. Research Background 106 6.2. Results and Discussion 109 6.2.1. Design and characterization of rm-PI 109 6.2.2. The proportion of NVC-segment in rm-PI/mx-mmol% 118 6.2.3. Molecular events during the damage-repair cycle 119 6.2.4. Self-healing performances of PI/m1_n2 in nano-scale thickness 126 6.2.5. Recyclability of PI/m1_n2 128 Chapter 7 – Conclusions and Future Works 130 7.1. Representative Conclusion for Chapter 3 130 7.2. Representative Conclusion for Chapter 4 130 7.3. Representative Conclusion for Chapter 5 131 7.4. Representative Conclusion for Chapter 6 132 7.5. Summary Conclusions 132 7.6. Future works 133 References 136

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