具有自修復性之智能材料，不論在自修復機制的建立或是材料的應用方面，近年來都受到研究者廣泛的注意。對熱固性自修復高分子材料而言，其自修復機制大抵可以分為自發性與非自發性自修復材料。前者為使用內包埋修復劑，其自修復行為由破壞材料引發，屬於一次性自修復行為，雖具有優異的自修復性，但無法重複與長期使用，如做為塗料之應用，則需長期更換。而非自發性自修復為利用可逆交聯反應建構的高分子自修復材料，雖須外加環境刺激以啟動自修復行為，但自修復性質可以重複實施，對於塗料以及其他保護性材料的應用，有其優勢。
因此，本研究利用不含修復劑之可逆交聯結構建立熱固性高分子自修復材料，使用兩種不同的環境因子作為自修復行為的啟動機制，即電與熱之刺激應答，並且將其應用於防腐蝕與其他商業塗料之等等應用。本研究以四部分進行，包括:
第一部分，利用防腐蝕單體-苯胺三聚體(amine-capped aniline trimer，ACAT)分子與商業用之汽車修補漆分別摻混至電致可逆交聯主客錯合物PGMA-Fc/Bis-CD，比較兩者之自修復與防腐蝕之性質，證實摻混在汽車修補漆與防腐蝕單體-苯胺兩者其保護效率皆可達到88%以上，並且各別在給予傷痕後之電致修復下之保護效率也可達到86%以上，進而摻混後之塗料皆可同時具有防腐蝕與自修復之特性。而ACAT單體可與電致可逆交聯主客錯合物PGMA-Fc/Bis-CD有協同效應，可使塗層具有防腐蝕性並且增強其自修復效果，成為優異之電致自修復防腐蝕材料。
第二部分，進行多官能基之可逆交聯反應，合成帶有呋喃官能基之苯胺單體ACAT-Fu4，及兼具貼附性之米氏酸及呋喃官能基之單體MAFBCB，個別與多馬來醯胺與多呋喃官能基之單體，M3與TFY，以不同進料配置進行Diels–Alder反應，為熱致反應自修復與防腐蝕材料，命名為self-healing and anti-corrsion，SHAC樣品組，分別為SHAC-A與SHAC-MA組材料。SHAC-A50與SHAC-A20Y展現優異的效果，其保護效率皆超過98%，而在自修復防腐蝕性質中，在二次熱致修復後，其保護效率為96%以上；另外，SHAC-MA20與SHAC-MA20Y其保護效率達到90 %以上，並且SHAC-MA20、SHAC-MA50與SHAC-MA20Y，而自修復防腐蝕實驗中，在高溫熱致二次修復後與長時間日照下，其保護效率皆為88 %以上。
第三部分，發展可逆醯胺鍵結應用於自修復材料中，利用烯酮(ketene)官能基與具有側碳鏈之二級胺(amine)，在室溫下進行可逆醯胺反應，且於45 ℃左右進行逆反應，恢復回ketene與amine官能基的狀態；因而利用帶有米氏酸之聚二甲基矽氧烷(Meldrum’s acid-containing polydimethylsiloxane，PDMSMA)，使之進行開環成為帶有烯酮(ketene)官能基的PDMSMA-ketene再與具有側碳鏈之雙邊二級胺(amine)進行醯胺反應成為塊材材料PDMSMA-ketene/diamine，而當PDMSMA-ketene/diamine材料受到損傷時，可分別在室溫一天與戶外太陽光照射下靜置一天進行自修復，恢復材料樣貌，成為新穎的動態共價化學方式之自修復材料，並且摻混在商業用之汽車修補漆中，可使塗料具有自修復特性。
　　第四部分，利用無機之多面體低聚倍半矽氧烷(methacryl POSS，MMA-POSS)，其分子帶有八個甲基丙烯酸官能基與具有呋喃官能基之有機單體(furfurylamine)進行反應，追蹤其反應機制，證實利用Michael Addition反應形成交聯有機凝膠，並具有自組裝的排列，而在膠體乾燥下溫度120 ℃，12小時進行狄耳士-阿德爾(Diels–Alder)反應，使之具有自修復的特性。

Self-healing polymer are interested by researcher in recent years, whatever to found the self-healing mechanism or the application of materials. For thermosetting self-healing polymer, the self-healing mechanism can be divided into two categories, spontaneous and non-spontaneous self-healing materials. spontaneous self-healing materials use repair agent in internal, the healing behavior caused by the destruction of materials, is a one-time self-healing behavior, although with excellent self-repair, but can not be repeated with long-term use. The non-spontaneous self-healing use of reversible reaction of polymer, although it need environmental stimuli to start healing, but the self-healing properties are advantages, can be repeated for the application of coatings and protective materials in coatings.
Therefore, in this study, a thermosetting self-healing polymer is constructed by using a reversible cross-linked structure without repairing agent. Two different environmental factors are used as the start up mechanism of self-healing behavior, electric and heat. Furthermore, the self-healing application in anti-corrosion and other commercial coatings and so on. The study is conducted in four parts.

　　First, Using the anti-corrosion monomer, amine-capped aniline trimer (ACAT), and the commercially car paint are blended on the electro-reversible crosslinked host-guest complexes PGMA-Fc / Bis-CD. Both coatings protection efficiency can reach more than 88%. after the coatings have the damage and get the electric healing, the protection efficiency can reach more than 86%. In addition to the ACAT monomer has a synergistic effect with the electro-reversible crosslinked host-guest complexes PGMA-Fc / Bis-CD, which makes the coating corrosion-resistant and enhances its self-healing effect, making it an excellent self-healing material.

In the second part, the reversible crosslinked reaction of multi-functional groups was carried out to synthesize ACAT-Fu4, which have furan functional groups in aniline, and MAFBCB, which is a combination of Meldrum's acid and furan functional groups. And multi-maleimide and multi-furan groups molecules, M3 and TFY, are used to mixed in different equivalent with ACAT-Fu4 or MAFBCB in Diels-Alder reaction, become to thermally induced self-healing and anti-corrosion materials, SHAC-A and SHAC-MA group materials. In the part one, SHAC-A50 and SHAC-A20Y show excellent results, the protection efficiency is more than 98%. After the second thermal repair in the self-healing and anti-corrosion test, the protection efficiency is 96%. In the second parts, SHAC-MA20 and SHAC-MA20Y with the protection efficiency of more than 90%. And SHAC-MA20, SHAC-MA50 and SHAC-MA20Y in the self-healing and anti-corrosion test, protection efficiency is more than 88%, after secondary repair and long time sunshine.

In the third part, the development of reversible amide bond is applied to the self-healing material. The reversible amide reaction is carried out at room temperature by using a ketene functional group and an amine group, having a side chain. As well as reverse reaction in the 45 ° C, to becoming the ketene and the amine functional groups. Thus, the polydimethylsiloxane with Meldrum's acid was used to open the ring reaction to form a PDMSMA with a ketene functional group PDMSMA-ketene. Using PDMSMA-ketene reacts with secondary amine, who having a side-carbon chain, to form the bulk material PDMSMA-ketene / diamine. When the PDMSMA-ketene / diamine material is damaged, it can heal at room temperature. It is a novel dyamic covalent chemicals method in self-healing material. Finally, blended in a commercially car paint, it can make the coating having the self-healing properties.

In the fourth part, using inorganic polytrimethoxysilane siloxane (Methacryl POSS, MMA-POSS) with its molecules with eight methacrylic acid functional groups and reaction in furan functional groups of organic monomer (Furfurylamine). The reaction mechanism is Michael Addition reaction to form crosslinked organic gel, and has a self-assembled arrangement, while the colloid drying temperature of 120 ℃, 12 hours Diels-Alder reaction , So that it has a self-healing properties.

摘要 I
Abstract III
致謝 V
目錄 VI
圖目錄 IX
表目錄 XVIII
第一章 緒論 1
1-1 前言 1
1-2 自修復材料之結構方式簡介 2
1-2.1 自修復材料之修復方式 2
1-2.2 自發性自修復材料 3
1-2.3 非自發性自修復材料 6
1-2.3.1 可逆交聯之共價鍵結 7
1-2.3.2 可逆交聯之非共價鍵結 11
1-3 環境應答自修復材料 15
1-3.1 電致自修復材料 15
1-3.2 光致自修復材料 20
1-3.3 酸鹼值致自修復材料 23
1-3.4 氧化還原致自修復材料 26
1-3.5 熱致自修復材料 29
第二章 自修復材料之應用 43
2-1 自修復與防腐蝕之應用 46
2-2 研究動機 58
第三章 電致可逆交聯超分子錯合物之自修復性質與防腐蝕應用 61
3-1 文獻回顧 61
3-2 實驗方法 67
3-2.1 實驗藥品 67
3-2.2 實驗儀器設備 67
3-2.3 電致自修復材料之製備 69
3-2.4 防腐蝕單體ACAT之製備 71
3-2.5 電致自修復材料之防腐蝕檢測製備 72
3-2.6 電化學之防腐蝕檢測方法 74
3-3 結果與討論 76
3-4 結論 88
第四章 多官能基之可逆交聯反應應用於自修復與防腐蝕 89
4-1 文獻回顧 89
4-2 實驗方法 92
4-2.1 實驗藥品 92
4-2.2 實驗儀器設備 93
4-2.3 實驗製備 95
4-2.3.1 ACAT-Fu4單體合成 95
4-2.3.2 M3單體合成 96
4-2.3.3 TFY單體合成 97
4-2.3.4 熱致自修復材料之抗腐蝕檢測製備 98
4-2.3.5 電化學抗腐蝕檢測方法 99
4-3 結果與討論 101
4-3.1 ACAT-Fu4單體鑑定 101
4-3.2 M3單體鑑定 104
4-3.3 TFY單體鑑定 107
4-3.4 添加ACAT-Fu4之可逆交聯自修復防腐蝕 110
4-3.5 添加MAFBCB之可逆交聯自修復防腐蝕 128
4-4 結論 142
第五章 醯胺鍵結之動態共價化學自修復材料 143
5-1 文獻回顧 143
5-2 實驗方法 146
5-2.1 實驗藥品 146
5-2.2 實驗儀器設備 147
5-2.3 實驗製備 148
5-2.3.1 MA-VB單體合成 148
5-2.3.2 PDMSMA高分子合成 149
5-2.3.3 PDMSMA-Ketene/diamine自修復膜之製作方法 150
5-2.3.1 PDMSMA-Ketene/diamine摻混於商業用汽車修補漆之製作方法 150
5-3 結果與討論 153
5-3.1 PDMSMA-Ketene/diamine之反應追蹤實驗 153
5-3.2 PDMSMA-ketene/diamine之自修復檢測 159
5-3.3 PDMSMA-ketene/diamine摻混於汽車修補漆之自修復檢測 163
5-4 結論 165
第六章 有機無機摻混之自修復材料 166
6-1 文獻回顧 166
6-2 實驗方法 169
6-2.1 實驗藥品 169
6-2.2 實驗儀器設備 170
6-2.3 膠體製備 171
6-3 結果與討論 173
6-4 結論 184
總結 185
參考文獻 187
發表期刊 201

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