臺灣博碩士論文加值系統

本研究中我們合成了13個具可見光吸收之查爾酮光起始劑(CY1~13)，經由核磁共振氫譜(1H-NMR)、碳譜(13C-NMR)及質譜法(FT-MS)進行其結構與分子組成確認。Part-1中，將具電子豐盈之三苯胺結構導入查爾酮之兩側，同時探討在三苯胺上有甲氧基結構對於性質上之差異，即無甲氧基結構為CY1，一個甲氧基結構為CY2，兩個甲氧基結構為CY3、CY4和四個甲氧基結構為CY5。Part-2中，於查爾酮結構的一側引入二甲基胺結構，而於另外一側同樣導入有無甲氧基之三苯胺結構(CY6~9)，利用二甲基胺自身提供氫的方式，使化合物不需要額外再添加氫予體。同時，亦探討另一側之三苯胺上有無甲氧基結構對於性質上之差異。於Part-3中，延續Part-2中具優良雙鍵轉化率的CY8進行一系列的改質藉以提升雙鍵轉化效率，將CY8中的三苯胺置換為其他共軛片段，如具有不同取代位置的萘環結構(CY10、CY11)，或苯並呋喃的CY12及苯並噻吩的CY13。經由Photo-DSC實驗，大部分化合物查爾酮所衍伸之光起始劑配方在三羥甲基丙烷三丙烯酸酯(TMPTA)的自由基聚合中均表現出較良好的雙鍵轉化效率。以UV為曝光光源下，Part-1中雙鍵轉化率為CY1 > CY4 > CY2 > CY5 > CY3，Part-2中雙鍵轉化率為CY8 > CY6 > CY7 > CY9，Part-3中雙鍵轉化率為CY12 > CY10 > CY11 > CY13;在LED@405 nm為曝光光源下，Part-1中雙鍵轉化率為CY4 > CY1 > CY2 > CY5 > CY3，Part-2中雙鍵轉化率為CY8 > CY6 > CY7 > CY9，Part-3中雙鍵轉化率則為CY12 > CY11 > CY10 > CY13。這些結果證明了苯胺衍生查爾酮為良好的光起始劑，可運用於UV及Vis不同光源，有助於光起始劑後續的發展。



關鍵字:自由基光聚合、UV光源、LED@405 nm光源、查爾酮光起始劑、三苯胺、二甲基胺、可見光

In this study, thirteen visible-light-absorbing chalcone photoinitiators have been synthesized and confirmed successfully through 1H-NMR、13C-NMR and Mass spectra. In Part-1, CY1~5 that contain peripheral triphenylamines at both sides with various methoxy substituents of the triphenylamine moiety were designed, that is hydrogen atoms only for CY1, one methoxy group on the triphenylamine for CY2, two methoxy groups on the triphenylamine for CY3 and CY4 and four methoxy groups on both triphenylamine sides for CY5. In Part-2, CY6~9 that contain one peripheral triphenylamine at one side with various methoxy substituents. At the same time, the dimethylamine is incorporated at another side. As a result, a series of one-component type II photoinitiators can be obtained. In Part-3, refer to the best double bond conversion efficiency in Part-2, ie. CY8, the triphenylamine moiety in CY8 was modified as a 1-, 2-position of naphthalene (CY10, CY11), a benzofuran of CY12 and a benzothiophene of CY13. Chalcone derivatives and their corresponding photoinitiator packages were prepared and employed to initiate the free radical photopolymerization of trimethylolpropane triacrylate (TMPTA) by using a photo-DSC instrument. Under UV lamp irradiation, the double bond conversion efficiency decreased in the following order: CY1 > CY4 > CY2 > CY5 > CY3 in Part-1, CY8 > CY6 > CY7 > CY9 in Part-2, and CY12 > CY10 > CY11 > CY13 in Part-3. Under LED light at 405 nm, the double bond conversion efficiency decreased in the following order: CY4 > CY1 > CY2 > CY5 > CY3 in Part-1, CY8 > CY6 > CY7 > CY9 in Part-2, and CY12 > CY11 > CY10 > CY13 in Part-3. Various results have proved that the chalcones are good photoinitiators, which can be used in UV and visible light irriadiation. This will help the subsequent development of photoinitiators, leading to more in-depth discussions in the future.




Keywords: Free radical photopolymerization, UV lamp, LED@405 nm, Chalcone photoinitiators, Triphenylamine, Dimethylamine, Visible light

目錄

摘要 i
ABSTRACT iii
致謝 v
目錄 vi
表目錄 xi
圖目錄 xii
一、緒論 1
二、文獻回顧與研究動機 2
2-1 光源介紹 2
2-1-1 UV光源 2
2-1-2 發光二極體(Light-emitting diode, LED) 2
2-2 深度聚合 4
2-3 光固化系統 5
2-3-1 光固化樹脂 6
2-3-2 光起始劑(Photoinitiator, PI) 7
2-3-2-1 陽離子型光起始劑 8
2-3-2-2 自由基型光起始劑 9
2-4 查爾酮固化系統 11
2-5 單分子系統(類Type I)取代雙分子系統(Type II) 16
2-6 三苯胺 17
2-7 研究動機 19
三、實驗方法 20
3-1 實驗架構 20
3-2 儀器設備 21
3-3 實驗藥品 25
3-4 溶劑 32
3-5 查爾酮衍生物之合成 35
3-5-1 三苯胺衍生查爾酮之合成(Part-1) 35
CY1-1 之合成(圖3-3) 36
CY1-2 之合成(圖3-4) 37
CY1 之合成(圖3-5) 38
CY2-1 之合成(圖3-6) 39
CY2-2 之合成(圖3-7) 39
CY2 之合成(圖3-8) 41
CY3-1 之合成(圖3-9) 42
CY3-2 之合成(圖3-10) 42
CY3 之合成(圖3-11) 44
CY4-1 之合成(圖3-12) 45
CY4 之合成(圖3-13) 46
CY5 之合成(圖3-14) 47
CYP1 之合成(圖3-15) 48
3-5-2 三苯胺改質衍生查爾酮之合成(Part-2) 49
CY6 之合成(圖3-17) 50
CY7 之合成(圖3-18) 51
CY8 之合成(圖3-19) 52
CY9之合成(圖3-20) 53
CYP2 之合成(圖3-21) 54
CY8’ 之合成(圖3-22) 55
3-5-3 末端推電子基衍生查爾酮之合成(Part-3) 56
CY10之合成(圖3-24) 57
CY11之合成(圖3-25) 58
CY12-1之合成(圖3-26) 59
CY12之合成(圖3-27) 60
CY13-1之合成(圖3-28) 61
CY13 之合成(圖3-29) 62
3-6 實驗方法 63
3-6-1熱性質分析 63
TGA 測量 63
DSC 測量 63
3-6-2紫外光/可見光光譜儀測量 63
3-6-3螢光光譜儀測量 63
3-6-4循環伏安法測量 64
3-6-5 Photo-DSC測量 64
3-6-6 LED@405nm測量 64
3-6-7 Photolysis測量 65
3-6-8電子順磁共振儀ESR測量 65
3-6-9 理論計算 65
四、結果與討論 67
4-1 查爾酮衍生物之結構鑑定 67
4-1-1 CY1之結構鑑定 67
4-1-2 CY2之結構鑑定 69
4-1-3 CY3之結構鑑定 72
4-1-4 CY4之結構鑑定 74
4-1-5 CY5之結構鑑定 77
4-1-6 CY6之結構鑑定 79
4-1-7 CY7之結構鑑定 82
4-1-8 CY8之結構鑑定 84
4-1-9 CY9之結構鑑定 87
4-1-10 CY10之結構鑑定 89
4-1-11 CY11之結構鑑定 92
4-1-12 CY12之結構鑑定 94
4-1-13 CY13之結構鑑定 97
4-2 熱性質 100
Part-1 100
Part-2 101
Part-3 103
4-3 光化學分析 106
4-3-1 UV/Vis及PL分析 106
Part-1 106
Part-2 108
Part-3 110
4-3-2 光解(Photolysis)分析 112
Part-1 112
Part-2 114
Part-3 115
4-3-3 電子自旋共振(ESR)分析 116
Part-1 116
Part-2 117
Part-3 118
4-4 電化學分析 120
Part-1 120
Part-2 122
Part-3 123
4-5 理論計算 125
Part-1 125
Part-2 127
Part-3 130
4-6 光聚合性質 134
Part-1光聚合 134
Part-2光聚合 140
Part-3光聚合 142
五、結論 146
六、參考文獻 147

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