含磷酸膽鹼雙離子之功能性嵌段共聚物塗層於熱塑型聚氨酯導管

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黃宇(Yu Huang) 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

含磷酸膽鹼雙離子之功能性嵌段共聚物塗層於熱塑型聚氨酯導管
(Functional Diblock Copolymer Containing Zwitterionic Phosphocholine and CHicable Benzophenone for Medical Coating on Thermoplastic Polyurethane Catheter)

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至系統瀏覽論文 (2027-9-1以後開放)

摘要(中)

熱塑性聚氨酯 (Thermoplastic polyurethane, TPU)是常見的生醫植入材料，具有優秀的生物相容性及機械性質。然而，TPU導管表面的高摩擦係數造成潤滑不足，嚴重影響病患的健康狀態。TPU的疏水性表面更易於吸引蛋白質與細菌的貼附，導致生醫材料長期使用下的不穩定與效能衰退。
為了克服這些缺點，我們選擇2-甲基丙烯醯氧乙基磷酸膽鹼 (MPC) ，以高生物相容性、親水性與防汙性質聞名的雙離子單體，應用於TPU表面改性。然而，礙於TPU表面的惰性與疏水性質，將親水性的MPC修飾並固定於TPU表面仍是一大挑戰。在本研究中，採用了帶有二苯甲酮基團的單體3-甲基丙烯醯氧基-2-羥基丙基-4-氧二苯甲酮 (MHPBP)。透過可逆加成-斷裂鏈轉移 (RAFT) 反應合成嵌段共聚物Poly (MPC-b-MHPBP)，經由簡易的浸塗處理對TPU導管進行了表面修飾。高分子鏈中的疏水結構MHPBP能透過二苯甲酮基團抓取TPU表面的氫原子，進行烴基插入交聯反應 (CHic) 將共聚物固定於TPU基材表層，將TPU導管修飾成親水潤滑的的表面。共聚物通過核磁共振氫譜 (1H NMR) 確認其組成與轉化率，再透過溶解度試驗決定適用的塗層用溶劑。塗層溶液由黏度計、表面張力計與紫外-可見光分光光譜儀分析其黏度、表面張力與透明度等物理性質。共聚物通過浸塗法沉積，在吸收UV光源的輻射能量後，在TPU導管表面進行光接枝反應。完成表面修飾後，使用全反射-傅立葉轉換紅外線光譜儀 (ATR-FTIR) 及X射線光電子能譜儀 (XPS) 確認雙離子共聚物 Poly (MPC-b-MHPBP) 與導管表面的鍵結；塗層的親水性由水接觸角測量驗證，並透過拉伸機進行摩擦試驗測量潤滑效果；進行細菌與蛋白質貼附實驗以檢驗導管表面的防汙性能；最後使用原子力顯微鏡 (AFM) 與掃描式電子顯微鏡 (SEM) 觀察薄膜表面型態與粗糙度。
本研究中，透過簡易的改質方式，將雙離子共聚物Poly (MPC-b-MHPBP)修飾於TPU表面，使導管表面具有良好的潤滑與防汙性能。得益於簡單而快速的塗佈程序，該光起始型MPC嵌段共聚物有望作為一種有效的表面改性材料應用於醫療器材領域。

摘要(英)

Thermoplastic polyurethane (TPU), is a common biomedical implant. However, the high friction and deficient lubrication of TPU catheters have a direct influence on the health status of each patient. Its hydrophobic surface also attracts bacterial adhesion and protein adsorption, resulting in long-term instability and failure of biomaterials.
To overcome these disadvantages, 2-methacryloyloxyethyl phosphorylcholine (MPC) which is known as a biocompatible, hydrophilic and antifouling monomer, was adopted in TPU surface modification. Nevertheless, immobilization of MPC on TPU remains a challenge. Due to the inertness and hydrophobicity of TPU, hydrophilic MPC was found difficult to adhere on TPU. In this study, benzophenone monomer 3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone (MHPBP) was developed. Diblock copolymer Poly (MPC-b-MHPBP) was synthesized via reversible addition-fragmentation chain transfer (RAFT) to modify TPU catheter via a simple dip coating process. MHPBP in the copolymer with hydrophobic domain was able to bind the copolymer to adjacent C-H groups on TPU surfaces via C, H insertion crosslinking (CHic) on the benzophenone group. The polymers were characterized by 1H nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), and solubility test. The coating solutions were analyzed by viscometer, surface tension, and UV-vis for transparency. The polymers were deposited via dip coating and photo-grafted on TPU tubes upon UV irradiation. The hydrophilicity of films was accessed by contact angle goniometer. The lubrication of modified TPU tube was measured by friction test using tensile machine. The immobilization of polymer on TPU substrate was studied with x-ray photoelectron spectroscopy (XPS). The roughness and morphology of coating films was characterized with atomic force microscopy (AFM). The antifouling properties were examined by bacterial adsorption test and protein adhesion test. In preliminary data, we found that the modified TPU surfaces became more hydrophilic, therefore provided good antifouling characteristic. Due to the simple, quick coating process, the photoreactive MPC-based diblock copolymer could be used as an efficient surface modifier.

關鍵字(中)

★ 光起始烴基插入交聯反應
★ 雙離子材料
★ 2-甲基丙烯醯氧乙基磷酸膽鹼
★ 可逆加成-斷裂鏈轉移聚合
★ 醫療塗層
★ 非特異性吸附
★ 熱塑型聚氨酯

關鍵字(英)

★ photo-induced C,H insertion crosslinking (CHic)
★ zwitterionic materials
★ 2-methacryloyloxyethyl phosphorylcholine (MPC)
★ reversible addition-fragmentation chain transfer (RAFT)
★ medical coatings
★ non-specific adsorption
★ thermoplastic polyurethane (TPU)

論文目次

中文摘要 i
Abstract iii
目錄 v
圖目錄 ix
表目錄 xi
化學品名詞簡稱 xii
聚合物名詞簡稱 xii
溶液名詞簡稱 xii
一、文獻回顧 1
1-1 熱塑型聚氨酯 1
1-1-1 熱塑型聚氨酯應用於醫療領域之優勢 1
1-1-2 熱塑型聚氨酯抗汙性能之缺陷 3
1-1-3 生物膜 3
1-1-4 熱塑性聚氨酯表面改質之研究 5
1-2 抗沾黏材料 8
1-2-1 聚乙烯吡咯烷酮(Polyvinylpyrrolidone, PVP) 8
1-2-2 雙離子高分子 9
1-2-3 2-甲基丙烯醯氧乙基磷酸膽鹼 (2-Methacryloyloxyethyl phosphorylcholine, MPC) 10
1-3 表面性質修飾方法 12
1-3-1 表面接枝 12
1-3-2 烴基插入交聯反應(C-H Insertion Crosslinking, CHic) 12
1-3-3 二苯甲酮(Benzophenone, BP) 13
1-3-4 二苯甲酮(BP)單體作為光起始劑之缺點 14
1-3-5 3-Methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone (MHPBP) 14
1-4 自由基聚合反應 (Free radical polymerization) 15
1-4-1 可逆加成斷裂鏈轉移 (Reversible addition-fragmentation chain transfer, RAFT) 15
1-4-2 可逆加成-斷裂鏈轉移聚合反應機制 16
1-4-3 鏈轉移試劑 17
1-4-4 鏈轉移試劑之選擇 18
1-4-5 起始劑之選擇 19
1-5 商用醫療裝置親水塗料 19
二、研究目的 20
三、實驗材料與方法 22
3-1 藥品與設備 22
3-1-1 藥品清單 22
3-1-2 儀器設備清單 23
3-2 材料合成與製備 23
3-2-1 合成Poly(2-methacryloyloxyethyl phosphocholine) (PMPC) 23
3-2-2 合成3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone (MHPBP) 24
3-2-3 合成Poly(MPC-b-MHPBP) (PMH) 24
3-2-4 熱塑性聚氨酯(TPU)基材準備 24
3-2-5 瓊脂平板(LB Agar Plate)製備 25
3-3 實驗方法 25
3-3-1 液態核磁共振氫譜 (1H NMR) 25
3-3-2 質譜法 (Mass Spectrometry, MS) 25
3-3-3 凝膠滲透層析儀 (Gel Permeation Chromatograph, GPC) 26
3-3-4 嵌段共聚物Poly(MPC-b-MHPBP)之溶解度 26
3-3-5 紫外-可見分光光度法 (Ultraviolet-Visible Spectrum Detector, UV-vis) 26
3-3-6 Poly(2-methacryloyloxyethyl phosphorylcholine-b-3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone), P(MPC-b-MHPBP)導管修飾 27
3-3-7 衰減全反射式傅立葉轉換紅外光譜儀 (Attenuated Total Reflectance-Fourier-Transform Infrared Spectroscopy, ATR-FTIR) 27
3-3-8 X射線光電子能譜儀 (X-ray Photoelectron Spectroscopy, XPS) 28
3-3-9 動態光散射儀 (Dynamic Light Scattering, DLS) 28
3-3-10 原子力顯微鏡 (Atomic Force Microscopy, AFM) 29
3-3-11 水下摩擦試驗 (Friction Test) 29
3-3-12 水接觸角測量 (Water Contact Angle Measurement) 30
3-3-13 蛋白質吸附測試 (Protein Adsorption Test) 30
3-3-14 細菌貼附測試 (Bacteria Adhesion Test) 31
3-3-15 統計學分析方法 31
四、結果與討論 32
4-1 聚合物性質測定 32
4-1-1 Poly (2-methacryloyloxyethyl phosphorylcholine-b-3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone), P (MPC-b-MHPBP)鑑定 (1H NMR) 32
4-1-2 質譜法 (MS)鑑定3-methacryloyloxy-2-hydroxypropyl-4-oxybenzophenone (MHPBP) 34
4-1-3 共聚物Poly(MPC-b-MHPBP)不同溶劑比例中溶解度測試 35
4-1-4 紫外-可見分光光譜儀分析 (UV-vis) 36
4-1-5 塗層溶液中共聚物粒徑分析 (DLS) 37
4-2 塗層性質檢驗 38
4-2-1 導管表面官能基測定 (ATR-FTIR) 38
4-2-2 表面元素測定 (XPS) 40
4-3 塗層表面形貌鑑定 43
4-3-1 原子力顯微鏡 (AFM) 43
4-4 浸塗表面修飾功能性測定 44
4-4-1 水下摩擦試驗 44
4-4-2 水接觸角測量 49
4-4-3 細菌貼附試驗 50
4-4-4 蛋白質吸附試驗 56
五、結論 60
六、未來展望 61
七、參考文獻 62

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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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