本研究使用精煉石油的副產物元素硫直接作為合成反應的原料，除基於2013年Pyun教授團隊所開發的逆硫化反應外，本研究也開發出新的硫化反應，據以製備新穎的含硫高分子材料，並探討其性質以及可能的應用。藉由新的硫化反應的研究，為元素硫過剩的問題提供新的出路，也開發出具有優異性質的新高分子材料。
本研究首先以含面體矽氧烷寡聚物(polyhedral oligomeric silsesquioxane, POSS)之(methyl-methacrylate-POSS, MMA-POSS)為單體，與元素硫直接進行逆硫化反應而製備具有反應性的POSS-硫複合高分子材料S-MMA-POSS。S-MMA-POSS可以藉由共交聯反應，有效地將自修復能力導入傳統的熱固性樹脂中，形成含有POSS的交聯高分子複合材料；此外，S-MMA-POSS也可以作為提升高分子材料在紅外光區穿透度的改質劑。其後，將元素硫的逆硫化反應擴展至米氏酸(Meldrum’s Acid)衍生物，以帶有苯乙烯基的米氏酸化合物(2,2,5-trimethyl-5-(4-vinylbenzyl)-[1,3]dioxane-4,6-dione, MA-MS)與硫進行加成反應，生成S-MA-MS高分子複合材料。進行逆硫化反應後，S-MA-MS因為含有動態的S-S鍵而具有自修復性質，且S-MA-MS仍然保有MA環的結構可供進一步進行開環交聯反應。因此， S-MA-MS可作為具有交聯以及自修復特性的功能性添加劑，賦予其他高分子自修復的性質。此外，具有四個氧原子的MA環與接上的S-S鏈段，增加材料對於Hg2+的親和性，加上MA環開環反應產生的二氧化碳帶來的自發泡性質，進一步製備出多孔性材料S-MA-MS-foamed，以提高材料的比表面積提升其吸附Hg2+的性能，應用於製備Hg2+吸附材料。
此外，本研究也開發一種直接利用元素硫為原料來製備高分子材料的反應，並命名為硫自由基轉移與偶合反應 (sulfur radical transfer and coupling reaction, SRTC reaction)。在這反應中，使用benzoxazine作為自由基受體，製備出具有高含硫成分的Polybenzoxazines，使用1H NMR與13C DEPT來分析元素硫與benzoxazine環之間的反應機制。此外，polybenzoxazine–sulfur複合材料具有動態S-S鍵，因此擁有自修復的特性。在此部分的研究中，展示如何使用新反應製備具自修復且具加工性的高分子材料，並且探討且提出此反應的反應機制。
本研究進一步發現元素硫與benzoxazine之間的反應機構與benzoxazine環的化學結構有關。使用13C DEPT來分析反應的機制，且得出以下結論:具有較高鹼度且較少立體結構障礙的benzoxazines傾向於進行thiolation反應形成硫酮官能基(C=S鍵)，形成硫酮化的benzoxazine。此反應提供新的且有方便的方法，利用元素硫來製備含有硫酮基的benzoxazine，除可以當作製備含硫熱固性樹酯的前驅物外，硫酮化後的benzoxazine也展現抗菌能力，尤其是對於對抗生素(penicillin)有抗性的菌種。

Elemental sulfur has been directly used as stock to prepare novel polymeric materials in this work to make all-out effort for the problem of excess sulfur. Besides using inverse vulcanization invented by Pyun groups at 2013 as our synthetic method, we also developed new reaction routes to prepare polymeric materials with intriguing properties.
First, a new reactive and functional hybrid (S-MMA-POSS) of polyhedral oligomeric silsesquioxane (POSS) and sulfur was prepared with a direct reaction between a multifunctional methacrylated POSS compound (MMA-POSS) and elemental sulfur (S8) through the “inverse vulcanization” process. This preparation bases on the design of a reactive building block possessing POSS cages and sulfur (S-S) chains for building up POSS-based self-healing materials, which could be obtained with self-curing the S-MMA-POSS hybrid and use of the S-MMA-POSS hybrid as a reactive and functional additive for conventional thermosetting resins. Moreover, the presence of the sulfur chains is also effective to enhance the transparency of the self-healing materials in mid-infrared region.
In the second part, a new reactive and functional polysulfide (S-MA-MS) possessing Meldrum's Acid (MA) moieties was prepared with a direct reaction between a MA compound (MA-MS) and elemental sulfur through the “inverse vulcanization” process. S-MA-MS is an effective building block for imparting self-healing ability to the corresponding thermally crosslinked MA-containing nanocomposites through a self-curing reaction and co-curing reaction with conventional thermosetting resins. This preparation is based on the design of a reactive building block possessing MA groups and polysulfide chains for building up MA-based self-healing materials, which could be obtained with self-curing the S-MA-MS and use of the S-MA-MS as a reactive and functional additive for conventional thermosetting resins. The presence of the polysulfide chains and MA groups can increase the mercury binding sites and self-foamed ability of S-MA-MS can extend the surface area. Both properties can effectively enhance mercury capture ability of material.
In the third part, the work reports a novel approach to prepare polymeric materials using elemental sulfur as a feedstock through the newly developed sulfur radical transfer and coupling (SRTC) reaction. With benzoxazine compounds as exmaples of radical acceptors in the SRTC raction, polybenzoxazines possessing high sulfur contents have been prepared. The reactions between elemental sulfur with benzoxazine rings have been traced with FT-IR, 1H NMR, and 13C-DEPT to demonsrates the SRTC reaction mechanism. Moreover, the prepared polybenzxaozine-sulfur hybrid materials show attractive self-healing property based on the dynamic S-S liankges. An effective reaction route and the corresponding self-healing sulfur-possessing polymeric materials are demonstrated.
For the last part, the reaction routes between benzoxazine compounds and elemental sulfur has been demonstrated to be dependent on the chemical structure of benzoxazines. Benzoxazines having high basicity and less steric hindrance tend to undergo thiolation reaction with formation of thioxo (C=S) groups. The route of thiolation reaction provides a new and effective method for preparation of thioxo-containing benzoxazine compounds using elemental sulfur as a feedstock. The reaction mechanism between benzoxazine and sulfur have been determined with 13C-distortionless enhancement by polarization transfer nuclear magnetic resonance spectroscopy. The thioxo-containing benzoxazines could be utilized as precursorsfor preparation of sulfur-containing thermosetting resins. Moreover, they also exhibit favorable antibacterial activity against drug-resistant bacteria compared to the standard antibiotic ampicillin. This work has demonstarted an example of direct utilization of elemental sulfur as a feedstock in material synthesis .

摘要 I
Abstract IV
序言 VII
目錄 VIII
圖目錄 XI
表目錄 XXII
第一章 緒論 1
1-1 前言 1
1-2 元素硫之利用方法: 物理製程簡介 3
1-2.1 熔化擴散法 4
1-2.2 氣相及溶液分散法 5
1-3 元素硫之利用方法: 化學製程簡介 9
1-3.1 陰離子反應 9
1-3.2 自由基反應 11
1-3.3 其它直接利用元素硫的化學反應 15
1-4 由Pyun團隊開發的「逆硫化反應」 16
1-5 研究目的 19
第二章 由多面體矽氧烷寡聚物為單體利用逆硫化反應製備自修復光學材料 21
2-1 文獻回顧 21
2-2 實驗藥品與儀器設備 32
2-3 實驗流程 34
2-4 結果分析與性質討論 35
2-5 結論 53
第三章 由米氏酸為單體利用逆硫化反應製備汞離子吸附材料 54
3-1 文獻回顧 54
3-2 實驗藥品與儀器設備 61
3-3 實驗流程 62
3-4 結果分析與性質討論 64
3-5 結論 80
第四章 硫自由基轉移與偶合反應的開發與應用 81
4-1 文獻回顧 81
4-2實驗藥品與儀器設備 86
4-3 實驗流程 87
4-4 結果分析與性質討論 89
4-5 結論 104
第五章 開發簡易製備含有硫酮基分子的方法與應用 105
5-1 研究背景 105
5-2實驗藥品與儀器設備 110
5-3實驗流程 112
5-4 結果分析與性質討論 117
5-5 結論 138
第六章 總結與展望 139
第七章 參考文獻 141

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