運用合理策略改善燃料電池薄膜之導電度,穿透度及強度

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研究生：	曾吉永 Chi-yung Tseng
論文名稱：	運用合理策略改善燃料電池薄膜之導電度,穿透度及強度 Using rational strategies to improve the conductivity, permeability and strength of fuel cell membranes
指導教授：	黃炳照 Bing-Joe Hwang
口試委員:	高憲明 none 陳志堅 none 林智汶 none 劉豫川 none
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：	2011
畢業學年度：	99
語文別：	英文
論文頁數：	148
中文關鍵詞：	薄膜、燃料電池、磺酸、石墨烯
外文關鍵詞：	membrane, fuel cell, sulfonated, graphite
相關次數：	點閱：309 下載：5
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本研究主要以混摻及交聯二種策略進行燃料電池質子交換膜之改質，並輔以各種物理化學分析技術，以鑑定合成質子交換膜之特性，其概分為以下三個部分來討論。
本文中第一部分主要探討磺化聚亞醯胺-聚矽氧烷共聚物的結構-性質關係。由於矽氧烷鏈段不相容親水鏈段，因此會影響離子叢聚的大小與分布，進而造成相分離。藉由相分離的產生，形成大量的離子傳輸渠道，進而增加質子導電度。為了比較矽氧烷在性質上的影響，另外再以擁有良好成膜性之4,4'-二氨基二苯醚與1,4,5,8-萘四甲酸酐進行聚亞醯胺的反應，進而來做一系列詳細的比較。
本文中第二部分主要藉由交聯劑的調控，在維持一定的導電度下，使甲醇穿透度降低。首先成功製備出具有高磺酸量的聚乙烯醇 [sulfonated poly(vinyl alcohol); SPVA]，為了使磺化聚乙烯醇於水合狀態下更穩定，因此使用交聯劑之策略。為了達成此目的，首先導入4,4'-聯苯醚二酐 (ODPA)與磺化聚乙烯醇上之羥基反應，形成游離態的羧酸基，而此羧酸基又可進一步與環氧樹脂反應。另外，環氧樹脂也能夠與磺化聚乙烯醇上之羥基反應，藉由相互間的反應性，造成高交聯度的形成。由於環氧樹脂具有獨特的性質，如;高水解穩定性、高耐化性與優異的撓曲性。因此，經由網狀交聯的結構，不只可以降低吸水率與甲醇穿透的問題，同時也可改善機械強度與水解穩定性。
本文中第三部分主要在探討磺化聚亞醯胺(sulfonated polyimide; SPI)與石墨烯氧化物(graphene oxide; GO)及具有聚苯乙烯磺酸石墨烯於質子交換膜之相互作用力。相較於原始磺化聚亞醯胺薄膜，比例0.5 wt%的石墨烯氧化物複合膜，其導電度於80 °C下增加5倍，甲醇穿透度降低5倍，同時，其機械性質於30 °C也增加1.3倍。因此，透過GO/SPI複合膜之設計，可顯著增進質子交換膜的性質。綜合以上，GO/SPI複合膜同時擁有各項優異特性，為一極具潛力應用於燃料電池之高分子電解質膜。

In this study, we used the blend and cross-linke two kinds of strategy to modification the proton exchange membrane in fuel cell. The emphasis is classiﬁed into three categories:
(Part 1) The focus of this work was the siloxane segmented with sulfonated polyimide and to study their structural-property relationships. The siloxanes are incompatible with the polyimides main chain as they influence the ordering and distribution of ionic clusters resulting in phase segregation. In addition, the ﬂexibility of the siloxane segments was expected to inhibit the formation of a dense, well packed polyimide structure. The phase segregation of incompatible siloxane domains can lead to the formation of ion-rich channels and improved proton conduction. Sulfonated polyimides without siloxane segments were also prepared using 4,4’-oxydianiline (ODA) for comparison: such ODA based polyimides are reported to have good ﬁlm-forming ability.
(Part 2) The aim of this study was to adjust the cross-linking agent mass to reduce the methanol permeability while retaining the membrane’s proton conductivity. To achieve this objective, we synthesised and characterized PVA bearing a high content of sulfonic acid groups. To ensure the dimensional stability of the hydrated membranes, the cross-linking agents were employed. Initially, 4,4’-Oxydiphthalic anhydride (ODPA) was reacted with the hydroxyl groups of the SPVA to generate an ionizable carboxylic acid, which was then able to react with further epoxy groups. Additionally, the epoxy was able to further react with the hydroxyl groups of SPVA, leading to a higher degree of cross-linking. The addition of the epoxy provided unique properties such as: high hydrolytic stability, high chemical resistance and excellent flexibility. Therefore, the cross-linked network structure was expected to not only improve the mechanical properties and hydrolytic stability, but also reduce the water uptake and methanol permeability of the membranes.
(Part 3) The goal of our investigation revealed structure-property relationships between graphene oxide (GO) and sulfonated polyimide (SPI). In addition to this we also present a chemical strategy to increase the sulfonic acid content of SPI membranes by incorporating graphene in the presence of poly(sodium 4-styrenesulfonate) (PSS-G). Compared to pristine SPI, the composites with 0.5 wt% GO show a 5-fold increase in proton conductivity and a 5-fold decrease in methanol permeability (at 80 ºC). Thus, through GO/SPI composite processing, composite membranes have been specifically designed to promote internal self-humidification, thereby increasing the PEMs water retention properties while easing water management, even at high temperatures and low humidities. Accompanying the positive trends for proton conductivity and methanol permeability was an increase in tensile strength, which was found to increase by 1.3-fold at 30 ºC. Based on the above, the composite membrane formed by our rational approach has excellent properties and may be a good candidate for polymer exchange membrane fuel cell applications.

摘要	I
Abstract	IV
LIST OF SCHEME	IX
LIST OF FIGURES	X
LIST OF TABLES	XIII
CHAPTER 1	1
1.1. Introduction to Proton Exchange Membrane Fuel Cells	1
1.1.1 The Generation of Power in the Future	1
1.1.2. Chemical Reactions Responsible for the Operation of a Fuel Cell	1
1.1.2.1 Hydrogen Fueled Proton Exchange Membrane Fuel Cells (PEMFC)	2
1.2.2.2 Direct Methanol Fuel Cells (DMFCs)	2
1.1.3. The Development of Polymer Electrolyte Membranes for Direct Methanol Fuel Cells (DMFCs)	5
1.1.4. Requirements for DMFC Membranes	6
1.1.4.1. Conductivity	9
1.1.4.2. Methanol Crossover	10
1.1.4.3. Thermal Stability	10
1.1.4.4. Lifetime	11
1.1.5 Scope of the research	12
CHAPTER 2	13
2.1. Polymer Systems for Proton Exchange Membranes	13
2.1.1. Nafion and Other Poly(perfluorosulfonic acid) Membranes	13
2.1.2. PEMs Based on Poly(arylene ether)s	15
2.1.2.1. Postsulfonation of Existing Polymers	15
2.1.2.2. Direct Copolymerization of Sulfonated Monomers to Afford Random (Statistical) Copolymers	19
2.1.3. PEMs Based on Poly(vinyl alcohol)s	24
2.1.4. PEMs Based on Poly(imide)s	26
2.2. Graphene	33
2.2.1. Discovery of graphene	33
2.2.2. Polymer/graphene nanocomposites	34
2.2.2.1. Nafion/graphene nanocomposites	35
2.2.2.2. Polystyrene/graphene nanocomposites	35
2.2.2.3 Polyaniline/graphene nanocomposites	38
CHAPTER 3. Tuning transport properties by manipulating the phase segregation of tetramethyldisiloxane segments in modiﬁed polyimide electrolytes	41
3.1. Introduction	41
3.2. Experimental	43
3.2.1. Materials	43
3.2.2. Synthesis	43
3.2.3. Preparation of composite membranes.	44
3.2.4. Membrane Characterizations.	45
3.3. Results and Discussion	48
3.3.1. Characterization of composite membrane	48
3.3.2. Thermal properties of the membranes	50
3.3.3. Morphology analysis	51
3.3.4. Ionic exchange capacity (IEC), λ, water content	54
3.3.5. Proton conductivity	56
3.3.6. Methanol permeability	58
3.4. Summary	59
CHAPTER 4. Interpenetrating Network-Forming Sulfonated Poly(vinyl alcohol) Proton Exchange Membranes for Direct Methanol Fuel Cell Applications	60
4.1. Introduction	61
4.2. Experimental	64
4.2.1. Materials	64
4.2.2. Synthesis of sulfonated poly (vinyl acetal)s	64
4.2.3. Preparation of membranes	64
4.2.4. The characterization of the cross-linked SPVA membranes	66
4.3. Results and Discussion	70
4.3.1. Chemical structure evaluation	70
4.3.2. Thermal properties	73
4.3.3. Water content, ionic exchange capacity (IEC) and oxidative stability	74
4.3.4. Proton conductivity	77
4.3.5. Morphology	79
4.3.6. Methanol permeability	80
4.3. Summary	85
CHAPTER 5. Sulfonated Polyimide Proton Exchange Membranes with Graphene Oxide show improved Proton Conductivity, Methanol Crossover Impedance and Mechanical Properties	86
5.1. Introduction	86
5.2. Experimental	89
5.2.1. Materials	89
5.2.2. Preparation of graphene oxide (GO) and sulfonated polyimide (SPI)	89
5.2.3. Preparation of SPI/GO and SPI/PSS-G composites	91
5.2.4. Materials Characterization	91
5.3. Results and Discussion	94
5.3.1. Morphology analysis	94
5.3.2. Small angle X-ray scattering (SAXS)	95
5.3.3. Thermal properties of the membranes	96
5.3.4. IEC and uptake behavior	97
5.3.5. Proton conductivity	101
5.3.6. Methanol permeability	103
5.3.7. Mechanical Properties	106
5.4. Summary	107
CHAPTER 6	108
Conclusions	108
Curriculum Vitae	129


LIST OF SCHEME
Scheme 3-1.  Structures of SPI, SPI_DSX, and PI_DSX	49
Scheme 3-2. 	Scheme showing the segregation of hydrophilic/hydrophobic domains in the prepared membrane	54


LIST OF FIGURES
Figure 1-1. 	Phenomena in a PEM fuel cell: two-dimensional sectional view	4
Figure 1-2. 	XRF traces showing ruthenium crossover to the cathode for two used 	membranes (open circle and square) vs. an unused membrane (open triangle). 	Reproduced by permission of The Electrochemical Society.	7
Figure 1-3. 	Illustration of proton transport in acidic aqueous solutions and in protic ionic  	liquids. Top: Grotthuss mechanism; the protons are passed along hydrogen  	bonds. Bottom: vehicle mechanism: the proton movement occurs with the aid  	of a moving ‘’vehicle’’ e.q., H2O and [Im]	9
Figure 2-1.  	Chemical structure of Nafion. X and y represent molar compositions and do not imply a sequence length	13
Figure 2-2. 		Several possible poly(arylene ether) chemical structures	16
Figure 2-3. 		Chemical structures of unsulfonated and sulfonated PEEK	17
Figure 2-4. 		Placement of the sulfonic acid group in postsulfonation (activated ring) versus 		direct copolymerization (deactivated ring)	19
Figure 2-5. 	Synthesis of 3, 3’-disulfonated 4, 4’-dichlorodiphenyl sulfone and its sodium salt	20
Figure 2-6. 	Chemical structures of unsulfonated and sulfonated PEEK	21
Figure 2-7. 		Atomic force micrographs of BPSH-40 and Nafion 117	22
Figure 2-8. 	Swelling in 30 oC liquid water for the BPSH series of copolymers	22
Figure 2-9. 	Some possible chemical structures for sulfonated PEMs from poly(arylene ether)s	23
Figure 2-10. 	Reaction scheme for the membrane preparation: representative structure of	26
Figure 2-11. 	Synthesis of SPI, a sulfonated six-membered ring polyimide based on BDSA, ODA, and NTDA	28
Figure 2-12. 	Six-membered ring copolyimide prepared with bulky unsulfonated diamine	30
Figure 2-13. 	Sulfonated diamines for direct synthesis of sulfonated polyimides	31
Figure 2-14. 	Synthesis of a five-membered ring sulfonated polyimide containing phosphine oxide	32
Figure 2-15. 	Sulfonated six-membered ring polyimides with noverl sulfonated diamines	33
Figure 2-16.	Graphene (top left) is a honeycomb lattice of carbon atoms. Graphite (top right)   can be viewed as a stack of graphene layers. Carbon nanotubes are rolled-up cylinders of graphene (bottom left). Fullerenes (C60) are molecules consisting of wrapped graphene through the introduction of pentagons on the hexagonal lattice (Reproduced with permission from Neto et al.)	34
Figure 2-17. 	Shematic diagram of the in-situ formation of PS/GNS nanocomposites. First (i)    GO and styrene monomer are emulsiﬁed together in SDS, then (ii) styrene is polymerized using KPS, and ﬁnally (iii) GO is reduced using hydrazine monohydrate resulting in the formation of PS/GNS nanocomposites	37
Figure 2-18. 	TEM images of PS/GNS nanocomposites at different magniﬁcations. It reveals that polystyrene microspheres with diameters in the range of 90-150 nm are attached to the surface of graphene especially along the edges of the stacked nanosheets with thicknesses of several nanometers	37
Figure 2-19. 	Raman spectra of the pristine GNS and PS/GNS nanocomposites	38
Figure 2-20. 	Illustration of the process for preparing PANI/graphene composites. (i) Aniline and GO are dispersed in amedium, (ii) aniline is oxidized to PANI (EB) using APS, (ii) GO is reduced to graphene using hydrazine, but at the same time PANI (EB) is also reduced to PANI (LB), hence (iv) PANI (LB) is again oxidized to PANI (EB) using APS	39
Figure 2-21 	TGA curves of GO, graphene, PANI, PANI/GO, and PANI/graphene (heating rate = 10 °C /min under a nitrogen atmosphere)	40
Figure 3-1.  	The 1H-NMR spectrum of SPI_DSX .	50
Figure 3-2.   The FTIR spectrum of SPI, SPI_DSX, and PI_DSX .	50
Figure 3-3.  	TGA thermodiagram, temperature held under 100 °C for 30 min and then raised to 900 °C	51
Figure 3-4. 	TEM micrographs of composite membrane: (a) SPI, (b) SPI_DSX10, (c) SPI_DSX30,  (d) SPI_DSX50, (e) SPI_DSX75, (f) SPI_DSX100, (g) PI_DSX50. (h) EDX analysis  for the image [1(g)] at (a) position 1 and (b) position 2	53
Figure 3-5.  	The water uptake, IEC of composite membranes as a function of SPI DSX amount .	56
Figure 3-6.  	Proton conductivity of composite membranes and Naﬁon117 membrane as a function of temperature, at 100% relative humidity.	58
Figure 4-1. 	Schematic diagram of cross-linked sulfonated PVA with ODPA and epoxy cross-linkers	65
Figure 4-2.  	(a) 1H-NMR and 13C-NMR spectrum of the SPVA. (b) 13C CP/MAS NMR spectrum of SPVA15	72
Figure 4-3.  	The FTIR spectrum of PVA, SPVA, and SPVA15	72
Figure 4-4.  	TGA thermodiagram, temperature held under 100 °C for 30 min and then raised to 900 °C	74
Figure 4-5.  	TGA thermodiagram, temperature held under 100 °C for 30 min and then raised to 900 °C	76
Figure 4-6.  	DSC melting curve of swelling membrane	77
Figure 4-7.  	Proton conductivity of composite membranes and Nafion117 membrane as a function of temperature, at 100% relative humidity	79
Figure 4-8.  	TEM micrographs of composite membrane: (a) SPVA3, (b) SPVA7, (c) SPVA10,  (d) SPVA15, (e) SPVA50	80
Figure 4-9.  	Methanol permeability of composite membranes at 30 °C with different methanol concentration	81
Figure 4-10. 	Stress-strain curves of composite membranes	82
Figure 4-11. 	The performance comparison for the DMFCs with SPVA3, SPVA7 and Naﬁon117 membranes with a 3 M methanol fuel at 70 °C	84
Figure 5-1.  	Schematic representation of the preparation of the SPI.	90
Figure 5-2. 	TEM images of (a) 0 wt% (X400,000), (b) 0 wt% (X100,000), (c) 0.5 wt% (X100,000), (d) 0.9 wt% (X100,000); SEM images of SPI/GO:(e) 0.5 wt%, (f) 0.9 wt%	95
Figure 5-3.  	The SAXS data of ln[q4 I(q)] versus 10q2 curves of the membranes	96
Figure 5-4.  	TGA curves of GO and SPI/GO: 0 wt%, 0.5 wt%, 0.9 wt%.	97
Figure 5-5.  	Photographs of GO and PSS_G in deionized water, methanol and H2O/methanol dispersion	100
Figure 5-6.  	The water desorption curves of the composite membranes at 60 oC. The values correspond to the water diffusion coefﬁcients (×10−5 cm−2 s−1)	100
Figure 5-7.  	Influence of 60% relative humidity on the proton conductivity of the composite membranes at 60 oC and 90 oC	102
Figure 5-8.  	Proton conductivity of composite membranes and Nafion117 membrane as a  function of temperature, at 95% relative humidity	102
Figure 5-9.  	Methanol permeability of composite membranes at 30 oC and 80 oC	104
Figure 5-10. 	Scheme showing the GO loading in the prepared membrane	105
Figure 5-11. 	Selectivity of composite membranes and Naﬁon117 at 30 and 80 º C	105
Figure 5-12. 	Representative stress-strain behavior of the composite membranes.	106













LIST OF TABLES
Table 1-1.  	Classification of DMFC polymer membranes	8
Table 1-2.  	Effect of DMFC parameters on methanol crossover	11
Table 3-1. 	Characterization of IEC, Water uptake, Composition of state of water and Activation energy (Ea) of composite membranes and Nafion117	45
Table 3-2.  	Methanol transport properties of composite membranes and Nafion117	56
Table 4-1.   	The properties of membranes	66
Table 5-1.  	Properties of resultant composite membranes	99

                                

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