聚氧代氮代苯并環己烷 (polybenzoxazine，以下簡稱PBZ) 為一具自催化聚合效果的新型酚醛樹脂，近二十年來被廣泛的關注與研究也成為一新興的科研學門。PBZ 雖衍生自傳統的熱固性與熱塑性酚醛樹脂，青出於藍、更勝於藍，不僅傳統酚醛樹脂所具有的優點在其身上有了進一步突破，而且還具備許多獨有特異性質，諸如:硬化後收縮率極低、低熱膨脹係數、低介電性……等。但如此天賦異稟的新材料仍免不了產生了代償性的缺點：脆性，這對高分子材料而言是很大的致命傷，也大大限制了其可加工性與應用廣度，因此，PBZ增韌性質之探究與相關應用之拓展乃本篇研究的主要方向。
關於 PBZ 材料增韌性質之探討，主要利用兩種方式來進行實驗： (1)導入合成出的 PEO-b-PCL 高分子，利用其與 PBZ 基材產生的氫鍵作用力進行高分子混摻，使軟鏈高分子均勻分布於基材中以達增韌之效果； (2)將較柔軟的聚二甲基矽氧烷分別以合環和矽氫化反應共價鍵結 BZ 於主鏈上，來觀察韌性行為。以上兩實驗皆可在終端樣品上觀察到薄膜可撓曲現象，也增進了不少應用性。
另一方向的實驗主要以拓展應用為主，首先我們發現 PBZ 薄膜獨有的光熱性質在簡單連續的 UV 光照射和熱處理時於材料表面會產生氫鍵結構轉換現象，同時利用這種方法製備出 PBZ/silica 混摻薄膜，並發現這樣的薄膜具有超親水、超疏水的可逆性。其次，在聚二甲基矽氧烷與 PBZ 的系統中，我們利用其薄膜的低表面能疏水性，結合前段的薄膜光熱性質，利用簡單的光刻法在定義的面積處結合無電鍍法來建構一層金屬銅膜於其上，將可應用於軟性電路板。最後，新能源材料的開發在近期可說如雨後春筍，在聚二甲基矽氧烷與PBZ薄膜試片中我們觀察到疏油疏水的雙疏現象，無疑屬於綠色材料之範疇；此外，具偶氮苯和腈基並可形成高交聯密度的三嗪基團 (trazine ring) 之合成材料 PBZPhAzo-CN-A，也在實驗中顯現優越的熱性質和二氧化碳捕捉能力，可視為一新型的碳中和能源材料。

Albeit that the polybenzoxazine (PBZ) resin is derived from traditional phenolic resins, the performance in this kind of addition-polymerized and autocatalyzed phenolics system became an even more successful than that of conventional novolac, resole type phenolics and many other thermosets. However, these highly gifted properties were compensatory with added brittleness, this might devastatingly limit its potential applications and capabilities. In this study, we not only tried various means possible to overcome its shortcomings but also imperatively explore the new breakthrough of applications on PBZs.
The surface properties of PBZs were investigated in chapter 2 and chapter 4. It was found that an easy way of sequential UV and thermal treatments could be a switch between superhydrophobicity and superhydrophilicity, and the PDMS-PBZ system also shows an amphiphobic property which was capable of building up metal layers via electroless plating.
Chapter 3 and chapter 4 are related to the toughening effect on benzoxazine resin. The experiments were achieved by introducing flexible segments of PEO-b-PCL and polydimethylsiloxanes (PDMS) into PBZ thermosets, and utilized the methods of hydrogen-bonded blending and covalent bonded at the main chain, respectively.
In chapter 5, two nitrogen-doped microporous carbons (NMCs) were synthesized via polymerization, calcination, and KOH activation of BZAPh and BZACN. Both two NMCs displayed excellent thermal properties and CO2 uptake capacity

論文審定書 i
謝誌 ii
摘要 iv
Abstract v
Content vii
Figure Captions xii
Table Captions xix

Chapter 1 Introduction 1
1-1 Benzoxazine and Polybenzoxazine 1
1-2 Surface Properties of Benzoxazine 5
1-3 An Overview of Block Copolymer 7
1-4 Polydimethylsiloxane as a Toughening Segment for Thermosets 9
1-5 Polybenzoxazine: A New Candidate for CO2 Uptake and Sequestration 11
1-6 References 16

Chapter 2 Reversible Surface Properties of Polybenzoxazine and Silica Nanocomposites Thin Films 22
2-1 Background 22
2-2 Experimental Section 25
2-2.1 Materials 25
2-2.2 Synthesis of Allyl Functional Benzoxazine (B-ala) 25
2-2.3 Thin-Film Formation and Polymerization 25
2-2.4 Characterization 26
2-3 Result and Discussion 27
2-3.1 Thermal and UV Treatment of Cured BZ Films 27
2-3.2 Reversible Phenomenon upon the Surface of Cured BZ Films 28
2-3.3 X-ray Photoelectron Spectroscopy (XPS) of Cured BZ Films 29
2-3.4 Morphologies of PBZ-Silica Hybrid Thin Film and Reversible Cycle Times 32
2-3.5 Severe Hysteresis of ARCA on PBZ-Silica Superhydrophobic Surface 33
2-4 Conclusions 34
2-5 References 47

Chapter 3 Flexible Epoxy Resins Formed by Blending with the Diblock Copolymer PEO-b-PCL and Using a Hydrogen-Bonding Benzoxazine as the Curing Agent 51
3-1 Background 51
3-2 Experimental Section 54
3-2.1 Materials and Syntheses 54
3-2.2 Sample Preparation of Flexible Epoxy Resin 54
3-2.3 Characterization 55
3-3 Result and Discussion 56
3-3.1 Analyses of PA-OH and PEO-b-PCL 56
3-3.2 Analyses of Epoxy-Benzoxazine/PEO-b-PCL Mixtures Thermal Properties 56
3-3.3 Thermogravimetric Analysis of Cured PA-OH/Epoxy/PEO-b-PCL Blends 59
3-3.4 FTIR Spectroscopy Analysis of Cured PA-OH/Epoxy/PEO-b-PCL Blends 60
3-3.5 Mechanical Properties of Epoxy-Benzoxazine/PEO-b-PCL Mixtures 61
3-4 Conclusions 63
3-5 References 73

Chapter 4 Synthesis and Applications of Polysiloxane Containing Benzoxazine Moieties in the End Chain and Main Chain 77
4-1 Background 77
4-2 Experimental Section 79
4-2.1 Materials 79
4-2.2 Syntheses of P-ala 79
4-2.3 Synthesis of B-ala 80
4-2.4 Synthesis of P-ala-PDMS-580 via Hydrosilylation Reaction 80
4-2.5 Synthesis of B-ala-PDMS-580 via Hydrosilylation Reaction 81
4-2.6 Synthesis of Ph-PDMS-2500 81
4-2.7 Synthesis of BPA-PDMS-2500 81
4-2.8 Preparation and Thermal Treatment of BZs and BZ-PDMSs Samples 82
4-3 Result and discussion 83
4-3.1 Characterization of BZ and BZ-PDMS derivatives 83
4-3.2 DSC Curing Behavior of BZ and BZ-PDMS derivatives 84
4-3.3 Thermogravimetric Analysis of Cured BZ and BZ-PDMS Derivatives 85
4-3.4 Analyses of Glass Transition Temperature of DSC Thermograms and DMA- Tan δ
86
4-3.5 Surface Property (CAs) of Cured BZ and BZ-PDMS Derivatives and the Fingerprint Test 87
4-3.6 Application in Build up of a Cu(s) Metal Layer via Electroless Plating 89
4-4 Conclusions 89
4-5 References 100

Chapter 5 Nitrogen-Doped Microporous Carbons Derived from Azobenzene and Nitrile-Functionalized Polybenzo-xazines for CO2 Capture 104
5-1 Background 104
5-2 Experimental Section 107
5-2.1 Materials 107
5-2.2 Synthesis of AzoOHCN 108
5-2.3 Synthesis of BZAPh 108
5-2.4 Synthesis of BZACN 109
5-2.5 Thermal Curing Polymerization of BZAPh and BZACN 109
5-2.6 NMCs as The Derivatives of BZAPh and BZACN Monomers 109
5-3 Results and Discussion 110
5-3.1 Synthesis of the Monomers BZAPh and BZACN 110
5-3.2 Thermal Curing Polymerization of BZAPh and BZACN Monomers 111
5-3.3 Characterization of NMCs Deriving from BZAPh and BZACN Monomers 114
5-3.4 CO2 Capture Analysis of Poly(BZAPh)-A and Poly(BZACN)-A 117
5-4 Conclusions 118
5-5 References 131

Chapter 6 Conclusions and Future Outlook 136

About the Author 138

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