可控矽烷化：以耐水解甲基丙烯酸酯氮矽三環 於矽基材上作為功能性高分子之構成單元

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蔣竣東(Chun-Tung Chiang) 查詢紙本館藏

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化學工程與材料工程學系

論文名稱

可控矽烷化：以耐水解甲基丙烯酸酯氮矽三環於矽基材上作為功能性高分子之構成單元
(Controlled Silanization：Hydrolysis Resistance Methacrylate Silatrane as a Building Block for Functional Polymers on Silicon)

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至系統瀏覽論文 (2027-9-1以後開放)

摘要(中)

用於表面修飾的有機矽烷官能基(silane)因為其方便的快速製備、高實用性及對於不同表面材料皆有出色的效果而受到重視。商用的矽烷官能基3-(Trimethoxysilyl)propyl methacrylate (TMSPMA)已廣泛用在製備有機及無機混合材料，該結構的頭基具有三個甲氧基能與金屬表面的羥基反應形成穩定之共價鍵，而在末端官能基則有甲基丙烯酸官能基團能與其他單體進行高分子及交聯反應來形成帶有矽烷之功能性高分子。然而，矽烷官能基容易水解且不易保存的特性導致需要在無水的環境下進行反應，因此傳統的矽烷官能基限制了在工業上應用性。在本研究中，我們合成了具有三環籠狀結構和跨環狀氮矽配位鍵的甲基丙烯酸酯氮矽三環類化合物(Methylacrylate silatrane, MAST)，此結構在水中表現出優異的化學穩定性，此外MAST 能與生物啟發之雙離子材料 2-甲基丙烯醯氧基乙基磷酸膽鹼單體(2-Methacryloyloxyethyl phosphorylcholine, MPC)進行高分子反應並將抗汙性質應用在矽基材的表面。MAST 的化學結構使用了核磁共振光譜學(NMR) 及質譜儀(MS)來佐證其結構，另外利用了核磁共振光譜學、X射線光電子能譜學(XPS)、原子力顯微鏡(AFM)、橢圓偏光儀(Ellipsometry)及水接觸角(Water contact angle)等方法與商用矽烷官能基(TMSPMA)進行在水中的化學穩定性、分子取向、表面粗糙度、薄膜膜厚及潤濕性的比較。此外，抗污的雙離子材料MPC 與MAST 利用傳統自由基聚合成高分子用於玻璃修飾上，其出色的修飾平整性及親水能力，透過細菌及蛋白質的貼附測試來證實。本論文透過發展一種穩定且功能強大之甲基丙烯酸酯氮矽三環類化合物，並具有重複性、可定向性及性質定義明確以達到可控矽烷化的目的，進而推動於矽烷化學的發展。

摘要(英)

Organosilicons for surface modification are emphasized for their ease of rapid preparation high availability, and effective modification of different interfacial. The commercial silane 3- (Trimethoxysilyl)propyl methacrylate (TMSPMA) has been widely used in the preparation of organic/inorganic hybrid materials. The silane agent has a trialkoxysilyl group, which reacts with hydroxyl groups on the metal surface and then form Si-O-metal covalent bonds. The methacrylic functional group of the silane agent was firstly polymerized with the other monomers to form a silane-containing functional ploymer. However, TMSPMA is easy to be hydrolyzed, making it inconvenient to store, and requiring an anhydrous solvent for coating. The constrains of conventional metharylic silanes lead to troublesome for industrial implementations. In this study, we synthesized methylacrylate silatrane (MAST) with a tricyclic caged structure and a transannular N → Si dative bond, which shows excellent chemical stability in the presence of water. MAST was applied to co-polymerize with bio-inspired zwitterionic 2-Methacryloyloxyethyl phosphorylcholine (MPC) monomer for antifouling modification on silica surfaces. The chemical structure of the developed MAST was characterized by using nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS). The chemical stability in presence of water, molecular orientation, roughness, the film thickness and wettability of methacrylated silatranes were compared with commercially available TMSPMA by using NMR, X-ray photoelectron spectroscopy (XPS), atomic force microscope (AFM), ellipsometry, water contact angle, respectively. In addition, an antifouling zwitterionic MPC monomer was employed for constructing a functional copolymer with MAST by conventional free polymerization for surface deposition on silicon. The functionalities of coatings were verified by treating with hydrogel attachment, protein fouling test, and bacterial adsorption. The thesis contributes the advance of silane chemistry by developing a robust and stable acrylic organolsilane for reproducible, orderly oriented, well defined polymeric coating with an aim for controlled silanization.

關鍵字(中)

★ 可控矽烷化
★ 甲基丙烯酸酯矽烷官能
★ 非特異性吸附
★ 雙離子材料
★ 氮矽三環類化合物
★ 耐水解

關鍵字(英)

★ methacrylated silatranes
★ controlled silanization
★ zwitterionic materials
★ antifouling properties
★ hydrolysis resistance
★ silatrane

論文目次

中文摘要 i
Abstract ii
致謝 iv
目錄 v
圖目錄 viii
表目錄 x
一、文獻回顧 1
1-1 自組裝單層膜 1
1-1-1 矽烷官能基 2
1-1-2 氮矽三環類化合物 7
1-2 生物汙染 12
1-3 抗非特異性吸附之材料 13
1-3-1 非特異性吸附現象 13
1-3-2 抗沾黏材料特性 14
1-3-3 聚乙二醇材料 14
1-3-4 雙離子材料 15
1-3-5 PC類雙離子材料 16
二、研究目的 17
三、藥品清單與實驗設備 19
3-1 實驗藥品清單 19
3-2 實驗設備清單 21
3-3 材料合成 22
3-3-1 胺基氮矽三環(Amionpropyl silatrane, APS) 22
3-3-2 甲基丙烯酸酯氮矽三環(Methylacrylate silatrane, MAST) 22
3-3-3 合成p(MPC9-co-MAST1)高分子 23
3-3-4 合成p(MPC9-co-TMSPMA1)高分子 24
3-3-5 無水乙醇之製備 24
3-4實驗方法 25
3-4-1自組裝單層膜之製備 25
3-4-2 水接觸角之量測(Water contact angle) 25
3-4-3 薄膜厚度之量測(Ellipsometry) 25
3-4-5 表面型態之量測(AFM) 25
3-4-6 表面元素之量測(XPS) 26
3-4-7 甲基丙烯酸酯官能基活性之定性測試 26
3-4-8 凝膠滲透色譜分析(GPC) 26
3-4-9 細菌貼附測試(Bacteria attachment) 27
3-4-10 蛋白質貼附測試(Protein adsorption) 27
3-4-11 MAST與TMSPMA水解測試(Hydrolysis test) 28
3-4-12 統計分析 28
四、結果與討論 29
4-1 MAST化學結構鑑定與分析 29
4-1-1 胺基氮矽三環(APS)之1H NMR圖譜 29
4-1-2 甲基丙烯酸酯氮矽三環(MAST)之1H NMR圖譜 30
4-1-3 甲基丙烯酸酯氮矽三環(MAST)之質譜儀分析 31
4-2 比較使用MAST與TMSPMA進行表面修飾的差異性 32
4-2-1 MAST與TMSPMA水接觸角之量測 32
4-2-2 MAST與TMSPMA薄膜膜度之量測 33
4-2-3 MAST與TMSPMA 3D分子模型 34
4-2-4 MAST與TMSPMA表面元素分析 35
4-2-5 MAST與TMSPMA表面形貌分析 38
4-2-6 MAST與TMSPMA甲基丙烯酸酯官能基活性之定性測試 39
4-2-7 MAST與TMSPMA之水解測試 40
4-2-8 MAST與TMSPMA之FTIR圖譜 41
4-3高分子化學結構鑑定與分析 42
4-3-1 p(MPC9-co-MAST1)高分子之1H NMR圖譜 42
4-3-2 p(MPC9-co-TMSPMA1)高分子之1H NMR圖譜 43
4-3-3 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)高分子數據比較 44
4-4-1 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)水接觸角之量測 45
4-4-2 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)薄膜厚度之量測 46
4-4-3 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)表面元素分析 47
4-4-4 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)表面形貌分析 50
4-4-5 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)細菌貼附測試 51
4-4-6 p(MPC9-co-MAST1)與p(MPC9-co-TMSPMA1)蛋白質貼附測試 53
五、結論 54
六、未來展望 55
七、參考文獻 56

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指導教授

黃俊仁(Chun-Jen Huang)

審核日期

2022-9-12

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