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標題: | 新型仿生性兩性高分子材料合成及其在纖維素改性與色素吸附之應用 Synthesis and Application of Innovative Bio-mimic Zwitterionic Polymer in Cellulose Modification and Dye Adsorption |
作者: | 宋品儀 Pin-Yi Sung |
指導教授: | 梁文傑 Man-Kit Leung |
關鍵字: | 聚氨酯,兩性離子高分子,色素吸附,纖維素改性,紫外線/可見光分光光譜,貽貝黏附蛋白,鄰苯二酚, polyurethane,zwitterionic polymers,dye adsorption,cellulose modification,UV-VIS spectroscopy,mussel adhesive proteins,catechol, |
出版年 : | 2023 |
學位: | 碩士 |
摘要: | 本篇論文以二苯基甲烷二異氰酸酯做異氰酸酯官能基提供者,與帶有二元羥基的N-甲基二乙醇胺和自製含2,2-二甲基-1,3-苯並二氧戊環的三級胺化合物 (命名Cpd2) 分別進行加成聚合出聚氨酯同聚物,另結合兩者,以3:7之比例加成聚合出聚氨酯共聚物。
二苯基甲烷二異氰酸酯與N-甲基二乙醇胺同聚物以1,3-丙烷磺酸内酯修飾成兩性離子高分子,針對此化合物做色素吸附與纖維素改性實驗。用UV-VIS監測,可以發現經過1,3-丙烷磺酸修飾過的高分子在中性環境下即對吸附水性染劑甲基橙和亞甲基藍的效果良好,但對於非水性染劑的偶氮染色劑蘇丹三號就不具吸附能力,推測是因為聚氨酯本身就含有高極性的氨基甲酸酯基團,加上兩性離子高分子因為正負電荷分離而產生高極性,以至於對於僅溶在有機溶劑中的蘇丹三號不具吸附能力;除了本論文合成的兩性離子高分子,另使用三氧化二鋁和二氧化矽去做色素吸附比較。 將此高分子溶於三氟乙醇,在以纖維素為主要成分的定量濾紙上做表面塗層,不同介電常數 (Dielectric Constant) 的溶劑通過濾紙的趨勢有所不同。 另從自界中擷取貽貝黏附蛋白 (Mussel Adhesive Proteins, MAPs) 之靈感,貽貝黏附蛋白含有大量3,4-二羥苯丙氨酸,其中鄰苯二酚可以提供貽貝不怕水的黏著性,因此我們聚焦在鄰苯二酚,開發出1,3-苯駢二氧雜環戊熳和2,2-二甲基-1,3-苯並二氧戊環的去保護方式,產物命名為dCpd2,調和二苯基甲烷二異氰酸酯及dCpd2和兩性離子高分子共聚的比例,加入適量的軟鏈段、聚酯鏈段,可以應用在水性黏膠材料 (Waterborne Adhesive) 的開發。 This paper examines the synthesis of polyurethane copolymers using diphenylmethane diisocyanate as the provider of isocyanate functional groups. We form the copolymers through addition polymerization reactions involving N-methyl diethanolamine with binary hydroxyl groups and a tertiary amine compound called Cpd2, with a 2,2-dimethyl-1,3-benzodioxole ring structure synthesized in-house. Additionally, we synthesize a polyurethane copolymer by combining these components in a 3:7 ratio through addition polymerization. Furthermore, we investigate the synthesis of zwitterionic polymers by modifying diphenylmethane diisocyanate and N-methyl diethanolamine copolymers with 1,3-propane sultone. We then experimented with dye adsorption and cellulose modification using the modified polymers. Our UV-VIS monitoring results demonstrate that the sultone-modified polymers exhibit effective adsorption capabilities for water-soluble dyes such as methyl orange and methylene blue under neutral conditions. However, they do not possess adsorption capabilities for the non-aqueous dye Sudan III. This can be attributed to the high polarity of urethane groups in polyurethane and the high polarity resulting from separating positive and negative charges in the zwitterionic polymers. Consequently, the modified polymers cannot adsorb Sudan III, as it is solely soluble in organic solvents. We also compare the dye adsorption properties of the synthesized zwitterionic polymers with those of aluminum oxide and silica. When dissolving this polymer in trifluoroethanol and used for surface coating on quantitated filter paper with cellulose as the main component, it combined with custom-made glass for filtration experiments. In that case, the trend of solvent passage through the filter paper varies for single-layer, double-layer, and triple-layer surface coatings with different dielectric constants. Taking inspiration from mussel adhesive proteins (MAPs) obtained from self-adhering mussels, which contain a significant amount of 3,4-dihydroxyphenylalanine (DOPA), with its catechol group providing water-resistant adhesion, we focused on the catechol moiety. We developed deprotection methods for 1,3-benzodioxole and 2,2-dimethyl-1,3-benzodioxole, naming the products dCpd2. In the future, by finding the right balance between diphenylmethane diisocyanate, dCpd2, and zwitterionic polymers in copolymerization or by incorporating appropriate amounts of soft chain segments or polyester segments, we can explore their potential applications in the development of waterborne adhesive materials. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/91860 |
DOI: | 10.6342/NTU202304222 |
全文授權: | 未授權 |
顯示於系所單位: | 化學系 |
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