交聯之離子化聚苯並咪唑製備與陰離子交換膜燃料電池之應用

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研究生：	Zelalem Gudeta Abdi Zelalem Gudeta Abdi
論文名稱：	交聯之離子化聚苯並咪唑製備與陰離子交換膜燃料電池之應用 Synthesis and Characterization of Crosslinked Ionic Polybenzimidazole-Based Anion Exchange Membrane for Fuel Cell Applications
指導教授：	陳志堅 Jyh-Chien Chen
口試委員:	Chin-Yang Yu Chin-Yang Yu Kung-Li Wang Kung-Li Wang Ru-Jong Jeng Ru-Jong Jeng Ping-Yen Chen Ping-Yen Chen
學位類別：	博士 Doctor
系所名稱：	工程學院 - 材料科學與工程系 Department of Materials Science and Engineering
論文出版年：	2021
畢業學年度：	109
語文別：	英文
論文頁數：	129
中文關鍵詞：	陰離子交換膜、Thiol-ene反應、聚苯並咪唑、離子交換容量、鹼性穩定性
外文關鍵詞：	alkaline stability
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電化學轉換之燃料電池作為未來再生能源的主力有許多優點，其中陰離子交換膜能使用非貴金屬催化劑之特性更受到了學者們的關注，但仍有些問題需要解決，如較低的離子傳導率與待提升的機械強度和尺寸穩定性等等。本篇研究主要以交聯的手法調整並提升交換膜整體的性質，在第一篇研究中，我們運用商用品m-PBI進行改質，將四級銨鹽和雙鍵基團接枝於主鏈上，再利用thiol-ene反應進行熱交聯，藉由調整四級銨與雙鍵的比例控制離子交換容量(Ion exchange capacity, IEC)於1.51至2.50 mmol/g之間，並於攝氏80度下得到介於14至58 mS/cm的離子傳導率之陰離子交換膜。在相近的IEC下，交聯的陰離子交換膜能有相似的傳導率，但有更低的吸水率與更好的尺寸穩定性，室溫下其濕膜之抗拉強度介於10.8至14.6 MPa。而IEC=2.46 mmol/g的陰離子交換膜經過交聯，浸泡於60度的1 M氫氧化鈉水溶液720個小時後，能保留84 %的傳導率。
第二部分，我們同樣利用第一部分之陰離子交換膜，但另外導入疏水的乙烷基，能增加其溶解度，並使IEC的改質範圍增大至0.75~2.55 mmol/g。經過交聯過後的陰離子交換膜傳導率於80度時介於16~86 mS/cm之間，濕膜也有不錯的機械強度，抗拉強度介於12.2~20.1 MPa之間，楊式係數介於0.67~1.45 GPa。穩定性的測量上，0.40Q0.60Et1.00Pr (IEC=0.95 mmol/g)在經過80度的1 M氫氧化鈉水溶液720個小時後，只損失7.9 %傳導率。單電池性能上，60度時功率密度最高能到達136 mW/cm2，最大電流密度到達377 mA/cm2。本篇也會同時與第一篇中未加入乙烷基的陰離子交換膜做比較。
最後，我們同樣利用商用品m-PBI作為主鏈，四級銨作為側鏈，我們改以聚氯苯甲氯乙烯(PVBC)進行交聯，以重量比1:1的方式進行溶液塗佈以維持機械強度，其中1.35QPBI-PVBC具有108 mS/cm之離子傳導率，該薄膜具有更低的吸水率及更好的機械強度與尺寸穩定性。此外，其鹼性穩定性在經過80度的1 M氫氧化鈉水溶液720個小時後，只損失4.9 %傳導率與4.4 % IEC。經過一系列的研究後，我們認為這一系列交聯之PBI薄膜有做為陰離子交換膜之潛力。

Fuel cells are electrochemical tools that have been set up to lead the transition to renewable energy technology and will become the future energy efficient source. Among fuel cell system anion exchange membrane fuel cells are recently attention given. The basic environment opens the door for anion exchange membrane, the use of cheaper catalysts, which lower the cost barrier associated with proton exchange membrane fuel cells. However, anion exchange membranes exhibited, low ionic conductivity, low dimensional stability, and poor mechanical strength compared to proton exchange membrane, offsetting any potential cost advantage that may afford.
This dissertation demonstrates the crosslinking approaches of polybenzimidazle-based AEMs to solve the dilemma between ionic conductivity and dimensional change problem as well as to improve the alkaline stability of AEMs.
In the first work, we developed new anion exchange membranes using m-polybenzimidazole (m-PBI) as polymer backbone grafted with quaternary ammonium group and alkene group as side chains. Thiol-ene reaction was used to crosslink these ionic m-PBIs under thermal conditions. The ion exchange capacity (IEC) values and crosslinking degrees were monitored separately using the amount grafted quaternary ammonium groups and alkene groups, respectively. The prepared AEMs, IEC values ranged from 1.51 to 2.50 mmolg-1 show hydroxide conductivity of 14 to 58 mS/cm at 80 °C. With similar IEC values, crosslinked membranes consume less water but have similar hydroxide conductivity and greater dimensional stability than uncrosslinked membranes. A crosslinked membrane with an IEC value of 2.46 mmolg-1 will maintain 84% of its pristine hydroxide conductivity after being soaked in 1.0 M sodium hydroxide solution at 60 °C after 720 h. These membranes are also mechanically robust in the hydrated state, with tensile strengths ranging from 10.8 to 14.6 MPa at room temperature.
In the second work, new anion exchange membranes (AEMs) based on crosslinked polybenzimidazole (m-PBI) with quaternary ammonium groups, crosslinkable allyl groups, and hydrophobic ethyl groups as side chains are synthesized. The introduction of ethyl groups improved the solubility of ionic PBIs even at very low IEC values by eliminating the hydrogen bonding interaction of imidazole rings. This method allows ionic PBIs with broad IEC values, from 0.75 to 2.55 mmolg-1, to be prepared. The broad IEC values were achieved by independently controlling the numbers of quaternary ammonium groups, allyl groups, and hydrophobic ethyl groups during preparation. The crosslinked ionic PBIs showed hydroxide conductivity from 16 to 86 mS/cm at 80 °C. The wet membranes also showed excellent mechanical strength with the tensile strength of 12.2 to 20.1 MPa and Young’s Modulus of 0.67 to 1.45 GPa. The hydroxide conductivity of a crosslinked membrane (0.40Q0.60Et1.00Pr, IEC=0.95 mmolg-1) decreased only 7.9% after the membranes were immersed in a 1.0 M sodium hydroxide solution at 80 oC for 720 h. A single fuel cell based on this membrane showed a maximum peak power density of 136 mW/cm2 with a current density of 377 mA /cm2 at 60 °C. Introduction of the hydrophobic side chain to ionic PBI-based AEMs improved the alkaline stability, mechanical strength, and a single cell performance compared with that of without hydrophobic side chain as studied in the first work.
In the final work, to prepare the anion exchange membranes, which have high ionic conductivity, low dimensional change, and excellent alkaline stability, new crosslinked polybenzimidazole-based AEMs with poly(vinylbenzyl chloride) were synthesized. The partial quaternized polybenzimidazole is covalently crosslinked with poly(vinylbenzyl chloride) using solution casting methods. The mass ratio of partially quaternized polybenzimidazole to poly(vinylbenzyl chloride) was controlled by one to one, to maintained good mechanical strength. It demonstrated that the developed AEMs, show a well-defined nano-phase separation structure, leading to relatively high hydroxide conductivity of 108.56 mS/cm for 1.35QPBI-PVBC membrane. The prepared AEMs, relatively exhibit less water uptake and dimensional change, because of the existence of a strong crosslinking structure between the two polymers. In addition, the developed AEMs, also have good mechanical strength and excellent alkaline stability. 1.35QPBI-PVBC membrane, with higher ion exchange capacity (IEC=2.52 mmolg-1), only 4.9% hydroxide conductivity loss and 4.4% loss in ion exchange capacity observed, after soaking into 1.0 M KOH at 80 °C for 720 h. Based on our findings, crosslinked ionic m-PBIs We prepared to appear to be a promising candidate for use in fuel cells application as anion exchange membranes.

摘要    i
Abstract    iii
Acknowledgment    vi
Acronym    viii
List of Figures    xiii
List of Tables    xvi
List of Schemes    xvii
Chapter 1: Introduction    1
1. Background of Fuel Cells    1
2. Proton Exchange Membrane Fuel Calls (PEMFCs)    1
3. Anion Exchange Membrane Fuel Cells (AEMFCs)    3
Chapter 2: Literature Review    6
1. Materials as Anion Exchange Membranes    6
1.1. Polymer Backbone    6
1.1.1. AEMs Based on Poly(sulfone)s    7
1.1.2. AEMs Based on Poly(phenylene oxides) (PPOs)    9
1.1.3. AEMs Based on Poly(olefin)s    12
1.1.4. AEMs Based on Polybenzimidazoles (PBIs)    13
1.2. Cationic groups    18
1.3. The position of cationic group with the polymer backbone    19
2. Alkaline stability and degradation mechanism of AEMs    20
2.1. Alkaline stability of cationic groups    20
2.2. Alkaline stability of polymer backbone    21
3. Designed approaches    22
3.1. Crosslinked AEMs    22
3.1.1. Crosslinked AEMs via thiol-ene reaction    22
3.1.2. Crosslinked polybenzimidazole-based AEMs    25
3.2. Forming phase separation structure of AEMs    27
4. General Outline    28
5. Motivations and Objectives    29
5.1. Motivations    29
5.2. Objectives    30
Chapter 3: Experimental Section    32
1. Materials    32
2. Synthesis methods    32
2.1. Synthesis of m-polybenzimidazole (m-PBI)    32
3. Characterization methods    33
3.1. NMR characterization    33
3.2. Fourier transform infrared (FT-IR) spectroscopy characterization    33
3.3. Thermal gravimetric analyses (TGA)    33
3.4. Scanning electron microscope (SEM)    34
3.5. Atomic force microscope (AFM)    34
3.6. Mechanical testing    34
3.7. Ion exchange capacity (IEC) measurements    34
3.8. Water uptake (Wu) and dimensional change (DC) measurement    35
3.9. Gel fraction measurement    36
3.10. Hydroxide conductivity    36
3.11. Inherent viscosity    37
3.12. Alkaline stability    37
3.13. Fuel cell testing    38
Chapter 4: Anion Exchange Membranes Based on Ionic Polybenzimidazoles Crosslinked by Thiol-ene Reaction    39
1. Introduction    39
2. Synthesis methods    41
2.1. Grafting of m-polybenzimidazole with (5-bromopentyl) trimethyl ammonium bromide (Quaternary ammonium groups) (QA) and allyl bromide groups    41
2.2. Crosslinking membranes and anion exchange    42
3. Results and discussion    42
3.1. Synthesis of m-polybenzimidazole (m-PBI) and structural characterization    42
3.2. Synthesis and structural characterization of polybenzimidazoles grafted with (5-bromopentyl) trimethyl ammonium bromide (quaternary ammonium groups) and allyl bromide    44
3.3. Characterization of crosslinked AEMs    48
3.4. Properties of membranes    51
3.4.1. IEC, WU, DC, and hydroxide conductivity    51
3.4.2. Thermal stability of AEMs    55
3.4.3. Mechanical Properties of AEMs    56
3.4.4. Morphology of AEMs    58
3.4.5. Alkaline stability of AEMs    60
3.4.6. Single fuel cell performance    62
4. Summery    63
Chapter 5: Synthesis of Ionic Polybenzimidazoles-based Anion Exchange Membrane with Broad Ion Exchange Capacity Range for Fuel Call Application.    64
1. Introduction    64
2. Synthesis methods    67
2.1. Grafting of ethyl bromide, (5-bromopentyl) trimethylammonium bromide, and allyl bromide groups to m-PBI    67
2.2. Preparations of crosslinked AEMs and ion exchange    68
3.2. Membrane crosslinking and characterization    71
3.3. Membrane properties    74
3.3.1. IEC, WU, DC, gel fraction, and hydroxide conductivity    74
3.3.2. Thermal properties    77
3.3.3. Mechanical properties    78
3.3.4. Membrane morphology    79
3.3.5 Alkaline stability    80
3.3.6. Single fuel cell performance    82
4. Summery    83
Chapter 6: Synthesis of Crosslinked Ionic Polybenzimidazole-based Anion Exchange Membrane with Poly (vinylbenzyl chloride) for Fuel Cell Applications    84
1. Introduction    84
2. Synthesis methods    86
2.1. Synthesis of crosslinked xQPBI-PVBC AEMs    86
3.2. Membrane properties    92
3.2.1. IEC, WU, DC, gel fraction, and hydroxide conductivity    92
3.2.2. Thermal properties    95
3.2.3. Membrane mechanical properties    96
3.2.4. The morphology of the membrane    97
3.2.5. Alkaline stability    98
4. Summery    100
Chapter 7: Conclusions and Future Perspectives    102
1. Conclusions    102
2. Future perspectives    104
References    105
Appendixes    123

                                

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全文公開日期 2024/08/04 (校內網路)
全文公開日期 2031/08/04 (校外網路)
全文公開日期 2026/08/04 (國家圖書館：臺灣博碩士論文系統)

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