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研究生:林瑞崇
研究生(外文):Ruey-Chorng Lin
論文名稱:高效能與樹狀聚氧代氮代苯并環己烷:分子結構設計與特性行為研究
論文名稱(外文):High performance and dendritic polybenzoxazines: Molecular structure designs and characteristic behavior investigations
指導教授:郭紹偉郭紹偉引用關係
指導教授(外文):Shiao-Wei Kuo
學位類別:博士
校院名稱:國立中山大學
系所名稱:材料與光電科學學系研究所
學門:工程學門
學類:材料工程學類
論文種類:學術論文
論文出版年:2018
畢業學年度:106
語文別:英文
論文頁數:224
中文關鍵詞:香豆素樹枝狀高分子三苯胺聚氧代氮代苯并環己烷氫鍵高分子混摻氧代氮代苯并環己烷高分歧高分子
外文關鍵詞:BenzoxazineHyperbranched PolymerTriphenylamineDendrimerPolymer BlendingHydrogen BondingCoumarinPolybenzoxazine
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聚氧代氮代苯并環己烷發展至今已二十餘年,並受到許多相關的學術研究與工業應用的注視。在本研究中,針對高性能與樹狀等氧代氮代苯并環己烷衍生高分子進行研究。在高性能氧代氮代苯并環己烷衍生高分子的部份,藉由將其單體導入其他功能性官能基團 (如羧酸基團與香豆素基團),利用羧酸基團與聚乙烯吡咯烷酮混摻形成氫鍵交互作用力,以及經紫外光照射後香豆素基團進行[2π + 2π]環化加成反應與多價策略造成其交聯密度提升,皆能顯著提升其聚合物的熱穩定性。在樹狀氧代氮代苯并環己烷衍生高分子的部份,以便利的一鍋法曼尼希縮合聚合反應與獨特的投料程序,並選用三苯胺為分支單元,已成功合成一系列新穎的樹狀氧代氮代苯并環己烷衍生單體。氫與碳核磁共振光譜、紫外光/可見光吸收光譜、與螢光光譜可有效觀察單體的化學結構 (構型),尤其在不對稱結構之高分歧高分子的六元氧氮雜環會有特徵峰分裂的行為,以及其有效共軛長度隨著三苯胺單元數目增加而提升。特別的是樹枝狀高分子衍生物具有比高分歧高分子衍生物優異的熱穩定性,其可能的原因是樹枝狀高分子衍生物的核心單元使高分子鏈在高分子網狀結構中的移動性受到限制,以及其對稱性的結構所造成。在本研究中所有氧代氮代苯并環己烷衍生單體的熱開環反應放熱峰溫度皆比傳統的Pa型單體低 (263 oC),所以能有效改善氧代氮代苯并環己烷單體常見之高交聯溫度的問題。
Polybenzoxazines are developed for more than two decades and gained many attentions for academic researches and industrial applications. In this study, it focuses on the investigations of the high performance benzoxazine-base polymers and the dendritic benzoxazine-base polymers. For incorporating some functional groups (e.g., COOH and coumarin) into the benzoxazine monomers, the thermal stabilities of the polybenzoxazines can be enhanced significantly by using the hydrogen bonding interactions of the COOH moieties through blending with PVP [poly(N-vinyl-2-pyrrolidione)] and the crosslinking density increments through [2π + 2π] cycloaddition of the coumarin moieties upon UV irradiation as well as the multivalent strategies. A series of novel dendritic TPA-BZ monomers are synthesized successfully by using the triphenylamine as the branching group through facile one-pot Mannich condensations with a unique feeding approach. 1H and 13C NMR, UV-Vis absorption, and PL emission spectra can be used effectively to monitor the chemical constructions (conformations) of the dendritic TPA-BZ monomers, especially in the signal splitting behavior of oxazine rings for asymmetrical hyperbranched TPA-BZs and the effective conjugation length increment as the triphenylamine group increasing. Interestingly, the polymerized TPA-BZ dendrimers possess higher thermal stabilities than those of their hyperbranched counterparts, suggesting that the segmental mobilities in the polymer networks are restricted by the dendrimer core groups and their symmetrical chemical constructions. The temperatures of the exothermic peaks for all benzoxazine derivatives in this study are lower than that of the conventional Pa-type benzoxazine monomer (263 oC), resulting in improvement of the benzoxazine curing temperature too high issue.
Outline of Contents

論文審定書 i
謝誌 ii
摘要 iii
Abstract iv
Outline of Contents v
List of Tables x
List of Schemes xi
List of Figures xiv

Chapter 1 Introduction 1
1.1 Overview on Benzoxazines and Polybenzoxazines 1
1.1.1 Incorporating Reactive Groups into Benzoxazine Monomers 7
1.1.2 Intra- and Inter-Molecular Hydrogen Bonding Effect 10
1.2 Overview on Triphenylamines 15
1.3 Overview on Dendritic Polymers 16
1.3.1 Dendrimers 17
1.3.2 Hyperbranched Polymers 19
1.4 Motivation 23
1.5 References 25

Chapter 2 Coumarin- and Carboxyl-Functionalized Supramolecular Polybenzoxazines Form Miscible Blends with Polyvinylpyrrolidone 33
2.1 Background 33
2.2 Experimental 35
2.2.1 Materials 35
2.2.2 Synthesis of Coumarin-COOH BZ 35
2.2.3 Preparation of Coumarin-COOH BZ/PVP Blends 36
2.2.4 Photodimerization of Coumarin-COOH BZ 36
2.2.5 Poly(Coumarin-COOH BZ)/PVP Blends Through Thermal Curing 37
2.2.6 Measurements 37
2.3 Results and Discussion 38
2.3.1 Synthesis of Coumarin-COOH BZ Through Mannich Reaction of Coumarin-OH with 4-Aminobenzoic Acid and Paraformaldehyde 38
2.3.2 Thermal Polymerization of Coumarin-COOH BZ 39
2.3.3 Thermal Polymerization of Coumarin-COOH BZ/PVP Blends 43
2.3.4 Photodimerization of Coumarin Moieties Through [2π + 2π] Cycloaddition 49
2.4 Summery 54
2.5 References 55

Chapter 3 Multivalent Photo-Crosslinkable Coumarin-Containing Polybenzoxazines Exhibiting Enhanced Thermal and Hydrophobic Surface Properties 57
3.1 Background 57
3.2 Experimental 59
3.2.1 Materials 59
3.2.2 Synthesis of Bisphenol A-NO2 60
3.2.3 Synthesis of Bisphenol A-NH2 60
3.2.4 Synthesis of 1,3,5-Tris(4-nitrophenoxy)benzene 61
3.2.5 Synthesis of 1,3,5-Tris(4-aminophenoxy)benzene 62
3.2.6 Synthesis of Mono-Coumarin BZ 63
3.2.7 Synthesis of Di-Coumarin BZ 63
3.2.8 Synthesis of Tri-Coumarin BZ 65
3.2.9 Thermal Curing of Mono-, Di-, and Tri-Coumarin BZ 67
3.2.10 Photodimerization of Coumarin-Functionalized Benzoxazine 68
3.2.11 Samples of Coumarin-Functionalized Benzoxazines for Contact Angle Measurements 68
3.2.12 Measurements 69
3.3 Results and Discussion 70
3.3.1 Preparation for Three Different Functionalities of Coumarin Moieties Functionalized Benzoxazine Monomers 70
3.3.2 Characterization of Mono-Coumarin BZ 71
3.3.3 Characterization of Di-Coumarin BZ 73
3.3.4 Characterization of Tri-Coumarin BZ 76
3.3.5 TGA of Mono-, Di-, and Tri-Coumarin BZ 79
3.3.6 Photodimerization Through [2π+2π] Cycloaddition of Coumarin Moieties 81
3.3.7 Water Contact Angles of Photocrosslinked Coumarin-Functionalized PBZs 87
3.4 Summery 90
3.5 References 92

Chapter 4 Benzoxazine/Triphenylamine-Based Dendrimers Prepared Through Facile One-Pot Mannich Condensations 96
4.1 Background 96
4.2 Experimental 98
4.2.1 Materials 98
4.2.2 Synthesis of TPA-3NO2 99
4.2.3 Synthesis of TPA-3NH2 99
4.2.4 Synthesis of TPA-2NO2-OCH3 99
4.2.5 Synthesis of TPA-2NH2-OCH3 100
4.2.6 Synthesis of TPA-2NHCOCF3-OCH3 100
4.2.7 Synthesis of TPA-2NHCOCF3-OH 101
4.2.8 Synthesis of TPA-2NH2-OH 101
4.2.9 TPA-BZ Dendrimers 102
4.2.10 Thermal Curing of TPA-BZ Dendrimers 104
4.2.11 Measurements 104
4.3 Results and Discussion 105
4.3.1 Preparation of TPA-3NH2 as a Focal Group for TPA-BZ Dendrimers 105
4.3.2 Preparation of TPA-2NH2-OH as Branching Groups for TPA-BZ Dendrimers 107
4.3.3 Preparation of TPA-BZ Dendrimers of Various Generations 112
4.3.4 UV–Vis Absorption and PL Emission Spectra of TPA-BZ Dendrimers 121
4.3.5 Thermal Behavior of TPA-BZ Dendrimers 124
4.4 Summery 127
4.5 References 128

Chapter 5 Well-Defined Benzoxazine/Triphenylamine-Based Hyperbranched Polymers with Controlled Degree of Branching 131
5.1 Background 131
5.2 Experimental 136
5.2.1 Materials 136
5.2.2 Synthesis of TPA-BZ Monomer 136
5.2.3 Synthesis of TPA-BZ Trimer 137
5.2.4 Synthesis of Linear TPA-BZ Tetramer 138
5.2.5 Synthesis of TPA-BZ Tetramer 139
5.2.6 Synthesis of TPA-BZ DG1 140
5.2.7 Thermal Curing of Hyperbranched TPA-BZ Polymers 140
5.2.8 Measurements 141
5.3 Results and Discussion 141
5.3.1 Preparation of Four Types of Hyperbranched TPA-BZs and TPA-BZ DG1 141
5.3.2 1H NMR Spectral Analysis of Hyperbranched TPA-BZs and TPA-BZ DG1 144
5.3.3 13C NMR Spectral Analysis of Hyperbranched TPA-BZs and TPA-BZ DG1 163
5.3.4 DSC, FTIR, and MALDI-TOF Mass Spectroscopic Analyses of Hyperbranched TPA-BZs and TPA-BZ DG1 181
5.3.5 UV–Vis Absorption and PL Emission Spectra of Hyperbranched TPA-BZs and TPA-BZ DG1 184
5.3.6 Thermal Ring-Opening Polymerization of Hyperbranched TPA-BZs and TPA-BZ DG1 189
5.4 Summery 193
5.5 References 195

Chapter 6 Conclusions 199

Resume 202
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