光交聯及生物啟發磷膽鹽雙離子共聚物連續沉積醫療塗層於熱塑型聚氨酯材料

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江筠漢(Yun-Han 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

光交聯及生物啟發磷膽鹽雙離子共聚物連續沉積醫療塗層於熱塑型聚氨酯材料
(Medical Coating on Thermoplastic Polyurethane by Sequential Deposition of Photo-crosslinkable and Bio-inspired Zwitterionic Phosphocholine Copolymers)

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至系統瀏覽論文 (2027-9-12以後開放)

摘要(中)

熱塑型聚氨酯(Thermoplastic polyurethane, TPU)具有優異機械性質，被廣泛應用於各種用途，如:鞋墊、油漆塗料及手機保護殼等，而此材料亦具有良好生物相容性，因此可應用於醫療器材，例如:心導管、尿導管等等。但是聚氨酯導管具有一項缺陷，即是其表面的疏水性質，可能會造成蛋白質或是細菌的貼附，更進一步導致血栓，甚至是造成病患受到感染，因此熱塑形聚氨酯的表面修飾是一個令人重視的議題，主要目標是將表面修飾為親水性表面，並同時具有對抗蛋白質及細菌貼附的能力。在植入性的醫療器材中，器材的使用壽命也是十分重要的，所以必須利用化學性修飾使功能性高分子穩固地鍵結於表面。在此研究中，我們利用三種嵌段組成醫療性塗層: 其一，疏水性單體丙烯酸丁酯(BMA)與甲基丙烯酸月桂酯(DMA)能夠使共聚高分子物理吸附於聚胺酯表面；其二，光起始交聯單體3-甲基丙烯醯氧基-2-羥丙基-4-氧化二苯甲酮(MHPBP)；其三，親水性雙離子單體2-甲基丙烯醯氧乙基磷酸膽鹼(MPC)，其擁有優異的抗沾黏及生物相容性質，因此被廣泛使用。我們的表面修飾是建構在雙層塗層的架構上，含有MHPBP之高分子透過光起始之烴基插入交聯反應，扮演聚氨酯基材和MPC共聚物間的橋接夾層；第二層修飾層為功能性塗層，共聚中的主要成分MPC賦予此塗層抗沾黏特性以及潤滑度。以上提及的兩種高分子皆是透過傳統的自由基聚合反應合成，反應後之產物利用核磁共振光譜儀以及紫外光¬-可見光光譜儀進行特性分析。使用接觸角測量儀量測修飾塗層的潤濕特性；X射線光電子能譜儀及衰減全反射傅立葉轉換紅外光譜儀分析修飾塗層表面組成及接枝情形；原子力顯微鏡及掃瞄電子顯微鏡檢測塗層表面粗糙度、表面形貌及修飾厚度；拉伸測試機透過摩擦力測試量測修飾後導管之潤滑度；蛋白質及細菌貼附測試檢測塗層的抗沾黏特性。在初步的實驗中，我們調整塗層配方以及探討操作參數對塗層的影響，例如:MHPBP在PX共聚物中所佔的莫耳比例、MPC在MPC共聚物中所的莫耳比例、PX共聚物的溶解度、共聚物濃度、紫外光曝照時間以及紫外光曝照波長。以上所提及之變因會藉由改變塗層之穩定性、抗沾黏特性及潤滑度，進而影響醫療塗層的品質。因為研究中所使用塗層是透過化學鍵結進行修飾，相較於物理吸附，化學鍵結具有較良好的穩定性，因此希望此塗層在未來能夠被應用於醫療器材的製造中。

摘要(英)

Thermoplastic polyurethane (TPU) is a widely used biomaterial. It was found to have some serious problems, such as thrombosis and bacterial or protein adsorption that will cause the infection of the patients due to its hydrophobic properties. Therefore, it is an important issue to modify the TPU surface with hydrophilic properties, and the properties to prevent the adsorption of bacteria and proteins. Chemical modification of functional polymers is crucial for long-term and indwelling applications for medical devices. In this work, we applied three building blocks for constructing medical coatings: First, hydrophobic monomers, butyl methacrylate (BMA), and dodecyl methacrylate (DMA), for physical adsorption of polymers on TPU. Second, photo-crosslinkable benzophenone monomer, 3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone (MHPBP). Third, hydrophilic 2-methacryloyloxyethyl phosphorylcholine (MPC), which is a widely applied zwitterionic monomer, due to its outstanding antifouling and biocompatibility. The coating strategy was established based on a two-layer scheme. The first layer as a mediate layer containing MHBPB to serve as a crosslinking adlayer between MPC copolymer and TPU through photo-induced C,H insertion crosslinking (CHic). The second layer as a functional layer with the major component of MPC for fouling resistance and high lubrication. Two polymers were synthesized by conventional free radical polymerization and characterized by Nuclear Magnetic Resonance spectroscopy (NMR) and Ultraviolet–visible spectroscopy (UV-Vis). The wettability of the coatings was tested by the contact angle goniometer. The immobilization of the layers was examined by X-ray photoelectron spectroscopy (XPS) and Attenuated total reflectance-Fourier transform infrared spectra (ATR-FTIR) measurement. The roughness and the morphology of the coating layers on TPU were examined by Atomic Force Microscope (AFM). The thickness of the coating layers was analyzed by Scanning Electron Microscope (SEM). Lubrication of the coating was characterized by friction tests with the universal test machine. The antifouling properties of the coated TPU tubes were studied by protein and bacterial adsorption tests. In preliminary data, we formulated the coating solutions and discovered some key operation parameters, the molar ratio of MHBPB in the copolymer of the first layer, the solubility of co-polymers, co-polymer concentration, UV time, and UV wavelength. Those can considerably affect the quality of medical coatings in terms of stability, antifouling properties, and lubrication. In the future, due to the stability of the chemical modification, hoping that the coating process can be applied to the manufacturing of medical devices.

關鍵字(中)

★ 光起始烴基插入反應
★ 雙離子材料
★ 2-甲基丙烯醯氧乙基磷酸膽鹼
★ 醫療塗料
★ 非特異性吸附
★ 熱塑性聚氨酯

關鍵字(英)

★ photo-induced C,H insertion crosslinking
★ zwitterionic materials
★ 2-methacryloyloxyethyl phosphorylcholine (MPC)
★ medical coating
★ non-specific adsorption
★ thermoplastic polyurethane

論文目次

中文摘要 i
Abstract iii
致謝 v
目錄 vi
表目錄 xiii
化學品名詞簡稱 xiv
共聚物名詞簡稱 xiv
一、文獻回顧 1
1-1 熱塑型聚氨酯(TPU)之應用與困境 1
1-2醫療設備相關感染 (Device-Associated Infection, DAI) 2
1-2-1生物薄膜之形成 3
1-2-2凝血級聯反應 4
1-3表面修飾之方法 5
1-3-1烴基插入交聯反應(C,H insertion crosslinking, CHic) 7
1-3-2水凝膠貼附 8
1-4使用二苯甲酮(BP)單體進行表面修飾之缺點 9
1-5具有未來展望之二苯甲酮丙烯酸酯(BPA)共聚物 9
1-6抗沾黏材料 10
1-6-1 聚乙二醇(poly(ethylene glycol), PEG) 10
1-6-2 聚乙烯吡咯烷酮(poly(vinylpyrrolidone), PVP) 11
1-6-3雙離子高分子 12
1-6-3-1 磷酸膽鹼(phosphorycholine, PC) 13
1-7 醫用親水塗料之商業性產品 17
二、研究目的 18
三、實驗藥品與實驗方法 20
3-1實驗藥品與設備 20
3-1-1 藥品清單 20
3-1-2 設備清單 21
3-2材料製備 22
3-2-1 3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone合成 22
3-2-2 Poly(3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone-co-butyl methacrylate), P(MHPBP-co-BMA)合成 22
3-2-3 Poly(2-methacryloyloxyethyl phosphorylcholine-co-dodecyl methacrylate), P(MPC-co-DMA)合成 23
3-2-4 TPU基材製備 23
3-2-5 瓊脂平板制備 23
3-3 實驗方法 24
3-3-1 液態核磁共振光譜儀(1H NMR) 24
3-3-2 質譜儀分析(Mass spectrometry) 24
3-3-3 共聚物P(MHPBP-co-BMA)之溶解度分析 24
3-3-4 共聚物P(MHPBP-co-BMA)與MHPBP單反應效率與紫外光曝照 24
3-3-5 P(MHPBP-co-BMA)及P(MPC-co-DMA)之TPU導管修飾 25
3-3-6 衰減全反射傅立葉轉換紅外線光譜(Attenuated total reflectance-fourier transform infrared spectra, ATR-FTIR)分析鑑定 26
3-3-7 X射線光電子能譜儀(X-ray photoelectron spectroscopy, XPS) 26
3-3-8 水下摩擦力測試 26
3-3-9 水接觸角測定 (Contact angle meter) 27
3-3-10 蛋白質貼附測試 (Protein Adsorption Test) 28
3-3-11 抗細菌貼附測試 (Bacteria attachment Test) 29
3-3-12 原子力顯微鏡 (Atomic Force Microscope, AFM) 29
3-3-13 掃描電子顯微鏡 (Scanning Electron Microscope, SEM) 30
四、結果討論 31
4-1 單體合成性質鑑定 31
4-1-1 3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone, MHPBP之1H NMR光譜鑑定 31
4-1-2 3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone, MHPBP之質譜分析33
4-2 共聚物性質鑑定 34
4-2-1 Poly(3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone-co-butyl methacrylate), P(MHPBP-co-BMA)之1H NMR鑑定 34
4-2-2 溶劑對共聚物Poly(MHPBP-co-BMA)合成之影響 36
4-2-3 Poly(2-methacryloyloxyethyl phosphorylcholine-co-dodecyl methacrylate), P(MPC-co-DMA) 之1H NMR鑑定 37
4-2-4 共聚物Poly(MHPBP-co-BMA)在不同比例混合溶劑中的溶解度測試 39
4-3 紫外光波長及光照時間對MHPBP單體及其共聚物使用效率影響 40
4-4 浸塗修飾表面潤滑度分析 43
4-4-1 P(MHB)及P(MD)之單體組成比例對水下潤滑度的影響 43
4-4-2 塗層濃度對塗層潤滑度的影響 46
4-4-3 橋接高分子MH對潤滑度及耐磨性的影響 49
4-4-4紫外光曝照時間對導管修飾的影響 50
4-5 修飾表面親水性分析 53
4-6 導管表面修飾組成分析 54
4-6-1 導管表面之衰減全反射傅立葉轉換紅外線光譜(FTIR)分析 54
4-6-2 X射線光電子能譜儀表面元素分析 56
4-7修飾層表面形貌 58
4-7-1 原子力顯微鏡表面形貌及粗糙度測試 58
4-7-2 掃描電子顯微鏡塗層厚度量測 59
4-8 修飾表面抗貼附測試 60
4-8-1 導管表面蛋白質貼附測試 60
4-8-2 導管表面細菌貼附測試 61
五、結論 64
六、未來展望 65
七、參考文獻 66

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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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