研究生: |
楊承學 Cheng-Hsueh Yang |
---|---|
論文名稱: |
含2,2'-Bipyridine側基的聚醯亞胺之合成及其在水溶液中重金屬離子去除應用之探討 Synthesis of Polyimides Containing 2,2'-Bipyridine Side Group and Their Application in the Removal of Heavy Metal Ions in Aqueous Solutions |
指導教授: |
陳志堅
Jyh-Chien Chen |
口試委員: |
陳志堅
游進陽 江騏瑞 |
學位類別: |
碩士 Master |
系所名稱: |
工程學院 - 材料科學與工程系 Department of Materials Science and Engineering |
論文出版年: | 2020 |
畢業學年度: | 108 |
語文別: | 中文 |
論文頁數: | 99 |
中文關鍵詞: | 聚醯亞胺 、吸附 |
外文關鍵詞: | polyimide, adsorption |
相關次數: | 點閱:183 下載:0 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
本篇論文利用4,4'-oxydianiline (4,4'-ODA)和2,2'-bipyridine (BPy)為起始物合成新型二胺單體2-(2-bipyridinyl)-4,4'-oxydianiline (BPyODA(6)),再將BPyODA(6)與三種不同的商用品二酸酐以一步法合成新型聚醯亞胺系列(BPyODA系列)。BPyODA系列的聚醯胺酸固有黏度(inherent viscosity)為1.77~1.98 dL/g (0.5 g/dL, NMP, 35 ℃)。BPyODA系列的聚醯亞胺展現良好的熱穩定性,其玻璃轉移溫度介於279~331 ℃,5%熱重損失之熱裂解溫度(Td5%)介在441~522 ℃,10%熱重損失之熱裂解溫度(Td10%)介在462~554 ℃,在800 ℃時之熱殘餘重介在54~63 %。
將PI7a與PI7b進行Cu2+、Ni2+動力與等溫吸附實驗,實驗結果顯示,反應一天後,PI7a對Cu2+、Ni2+的吸附量分別為7.63及9.98 mg/g,PI7b對Cu2+、Ni2+的吸附量分別為22.24及10.56 mg/g,且PI7a與PI7b重複單元吸附Cu2+及Ni2+之效率則為PI7b較佳。動力學實驗結果,PI7a、PI7b與Cu2+之吸附行為,以擬二級動力式所模擬出的結果較佳,與Ni2+之吸附行為則以擬一級動力式所模擬出的結果較佳。等溫實驗結果,因Langmuir isotherm之R2值比Freundlich isotherm來的高,故以Langmuir isotherm較符合等溫吸附行為。添加5 mL正丙醇可使系統界面張力之能障降低、增加整體親水性,進而提升吸附容量。競爭吸附實驗中,溶液中含有兩種金屬離子的情況下,其吸附量依序:Cu2+大於Ni2+。
In this study, a new diamine monomer 2-(2-bipyridinyl)-4,4'-oxydianiline (BPyODA (6)) were synthesized by using 4,4'-oxydianiline (4,4'-ODA) and 2,2'-bipyridine (BPy) as starting materials. A series of novel polyimides (BPyODA series) were prepared from BPyODA (6) with various commercially aromatic dianhydrides by one steps method. These polyimides had inherent viscosities from 1.77 to 1.98 dL/g (0.5 g/dL, NMP, 35 ℃). They also exhibited good thermal stability, without any significant weight loss up to 400℃. These polyimides had high glass transition temperatures in the range of 279-331 ℃. The decomposition temperatures of these polyimides at 5% weight loss under nitrogen were in the range of 441-522 ℃. The decomposition temperatures of these polyimides at 10% weight loss under nitrogen were in the range of 462-554 ℃, and these residual weight percentage at 800℃ were 54-63%.
The kinetic and isotherm adsorption experiments were conducted by using PI7a and PI7b as adsorbents. The adsorption kinetics was found to follow the pseudo-second-order kinetic model(for Cu2+) and the pseudo-first-order kinetic model(for Ni2+) respectively. The equlilbrium data were best represented by Langmuir isotherm.The uptake capacities of PI7a obtained varied between 7.63 mg (for Cu2+) and 9.98 mg (for Ni2+) per one gram of polymer;The uptake capacities of PI7b obtained varied between 22.24 mg (for Cu2+) and 10.56 mg (for Ni2+) per one gram of polymer.The addition of a small amount of propanol decreases the interfacial tension of system drastically and increases the capacity of adsorption.The result of competitive adsorption test showed that Cu2+ is more dominant than Ni2+.
1.Hasegawa, M.; Horie, K. Photophysics, photochemistry, and optical properties of polyimides. Progress in Polymer Science 2001, 26 (2), 259-335.
2.Bogert, M. T.; Renshaw, R. R., 4-Amino-0-phthalic acid and some of its derivatives. Journal of the American Chemical Society 1908, 30 (7), 1135-1144.
3.Edwards, W. M.; Maxwell, R. I. Polyimides of pyromellitic acid. U.S Patents US2710853A, June 14, 1955.
4.Murray, E. W. Polyamide-acids, compositions thereof, and process for their preparation. U.S Patents US3179614A, April 20, 1965.
5.Laszlo, E. A. Process for preparing polyimides by treating polyamide-acids with lower fatty monocarboxylic acid anhydrides. U.S Patents US3179630A, April 20, 1965.
6.Vinogradova, S. V.; Vygodskii, Y. S.; Korshak, V. V. Some features of the synthesis of polyimides by single-stage high-temperature polycyclization. Polymer Science U.S.S.R. 1970, 12 (9), 2254-2262.
7.Liaw, D.-J.; Wang, K.-L.; Huang, Y.-C.; Lee, K.-R.; Lai, J.-Y.; Ha, C.-S. Advanced polyimide materials: Syntheses, physical properties and applications. Progress in Polymer Science 2012, 37 (7), 907-974.
8.Malinge, J.; Garapon, J.; Sillion, B. New developments in polybenzhydrolimide resins: Application in the field of heat resistant coatings, adhesives and laminates. British polymer journal 1988, 20 (5), 431-439.
9.Farrissey, W.; Andrews, P., Soluble copolyimides. U.S Patents US3787367A, January 22, 1974.
10.Critchley, J. A review of the poly(azoles). Progress in Polymer Science 1970, 2, 51-161.
11.Harris, F. W.; Hsu, S. L.-C. Synthesis and characterization of polyimide based on 3,6-diphenylpyromellitic dianhydride. High Performance Polymers 1989, 1 (1), 3-16.
12.Harris, F.; Sakaguchi, Y. Soluble aromatic polyimides derived from new phenylated diamines.(Retroactive Coverage). Polymeric Materials: Science and Engineering. 1989, 60, 187-191.
13.Vinogradova, S.; Korshak, V.; Vygodskii, Y. S.; Zaitsev, V. Polyamides based on aromatic diamines containing a phthalide or phthalimide group in the side chain. Polymer Science USSR 1967, 9 (3), 736-741.
14.Harris, F. W.; Feld, W. A.; Lanier, L. H. Soluble aromatic polyimides. The polymerization of phenylated bis(phthalic anhydrides) with diamine. Appl Polym Symp 1975, (26), 421-428.
15.Imai, Y., Synthesis of novel organic-soluble high-temperature aromatic polymers. High Performance Polymers 1995, 7 (3), 337-345.
16.Yang, C.-P.; Hsiao, S.-H.; Chen, K.-H. Organosoluble and optically transparent fluorine-containing polyimides based on 4, 4'-bis (4-amino-2-trifluoromethylphenoxy)-3, 3', 5, 5'-tetramethylbiphenyl. Polymer 2002, 43 (19), 5095-5104.
17.Wang, Z. Y.; Qi, Y. Poly(aryl prehnitimide)s. Macromolecules 1994, 27 (2), 625-628.
18.Li, F.; Kim, K.-H.; Savitski, E. P.; Chen, J.-C.; Harris, F. W.; Cheng, S. Z. Molecular weight and film thickness effects on linear optical anisotropy of 6FDA-PFMB polyimides. Polymer 1997, 38 (13), 3223-3227.
19.Cheng, S. Z.; Arnold Jr, F. E.; Zhang, A.; Hsu, S. L.; Harris, F. W. Organosoluble, segmented rigid-rod polyimide film. 1. Structure formation. Macromolecules 1991, 24 (21), 5856-5862.
20.Chern, Y.-T.; Twu, J.-T.; Chen, J.-C. High Tg and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2, 6-di-tert-butylbenzene. European polymer journal 2009, 45 (4), 1127-1138.
21.Chern, Y.-T.; Tsai, J.-Y. Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1, 4-bis (4-aminophenoxy)-2, 6-di-tert-butylbenzene. Macromolecules 2008, 41 (24), 9556-9564.
22.Matsuura, T. Optical waveguides using perfluorinated polyimides and their optical device applications. Linear and nonlinear optics of organic materials IV, International Society for Optics and Photonics: 2004, pp 73-80.
23.Maksin, D. D.; Kljajevic, S. O.; Dolic, M. B.; Markovic, J. P.; Ekmescic, B. M.; Onjia, A. E.; Nastasovic, A. B. Kinetic modeling of heavy metal sorption by vinyl pyridine based copolymer. Hemijska Industrija 2012, 66(6), 795-804.
24.Ballantine, D. S.; Martin, S. J.; Ricco, A. J.; Frye, G. C.; Wohltjen, H.; White, R. M.; Zellers, E. T., Chapter 5 - chemical and biological sensors. Acoustic Wave Sensors, 1997, pp 222-330.
25.Kecili, R.; Hussain, C. M. Chapter 4 - mechanism of adsorption on nanomaterials. Nanomaterials in Chromatography, 2018, pp 89-115.
26.Lagergren, S.; Sven, K. Zurtheorie der sogenannten adsorption gelösterstoffe. 1898.
27.Ho, Y.-S. Review of second-order models for adsorption systems. Journal of Hazardous Materials 2006, 136 (3), 681-689.
28.Chanda, M.; Rempel, G. L., Selective chromate recovery with quaternized poly(4-vinylpyridine). Reactive Polymers 1993, 21 (1), 77-88.
29.Sun, C.; Qu, R.; Xu, Q.; Chen, H.; Ji, C.; Wang, C.; Sun, Y.; Cheng, G. Preparation of crosslinked polystyrene-supported ethylenediamine via a S-containing spacer and adsorption properties towards metal ions. European Polymer Journal 2007, 43 (4), 1501-1509.
30.Awual, M. R. Ring size dependent crown ether based mesoporous adsorbent for high cesium adsorption from wastewater. Chemical Engineering Journal 2016, 303, 539-546.
31.Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Serroni, S. Luminescent and redox-active polynuclear transition metal complexes. Chemical Reviews 1996, 96 (2), 759-834.
32.Hancock, R. D. The pyridyl group in ligand design for selective metal ion complexation and sensing. Chemical Society Reviews 2013, 42 (4), 1500-1524.
33.Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P. l.; von Zelewsky, A. Ru (II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence. Coordination Chemistry Reviews 1988, 84, 85-277.
34.Wang, B.; Wasielewski, M. R. Design and synthesis of metal ion-recognition-induced conjugated polymers: an approach to metal ion sensory materials. Journal of the American Chemical Society 1997, 119 (1), 12-21.
35.Cumper, C.; Ginman, R.; Vogel, A., Physical properties and chemical constitution. Part XXXV. The electric dipole moments of some phenanthrolines and bipyridyls. Journal of the Chemical Society (Resumed) 1962, 226,1188-1192.
36.Dong, Y.; Koken, B.; Ma, X.; Wang, L.; Cheng, Y.; Zhu, C. Polymer-based fluorescent sensor incorporating 2, 2'-bipyridyl and benzo [2, 1, 3] thiadiazole moieties for Cu2+ detection. Inorganic Chemistry Communications 2011, 14 (11), 1719-1722.
37.Talanova, G. G.; Zhong, L.; Bartsch, R. A. New chelating polymers for heavy metal ion sorption. Journal of applied polymer science 1999, 74 (4), 849-856.
38.Pearson, R. G. Hard and Soft Acids and Bases. Journal of the American Chemical Society 1963, 85 (22), 3533-3539.
39.Pearson, R. G. Hard and soft acids and bases, HSAB, part II: Underlying theories. Journal of Chemical Education 1968, 45 (10), 643.
40.Pearson, R. G. Hard and soft acids and bases, HSAB, part 1: Fundamental principles. Journal of Chemical Education 1968, 45 (9), 581.
41.Talanova, G. G.; Zhong, L.; Kravchenko, O. V.; Yatsimirskii, K. B.; Bartsch, R. A. Noble metal ion sorption by pyridyl and bipyridyl group‐containing chelating polymers. Journal of applied polymer science 2001, 80 (2), 207-213.
42.Qu, R.; Sun, C.; Jl, C.; Wang, C.; Zhao, Z.; Yu, D.; Qu, R.; Sun, C. Synthesis and adsorption properties of macroporous cross-linked polystyrene that contains an immobilizing 2,5-dimercapto-1,3,4-thiodiazole with tetraethylene glycol spacers. Polymer Engineering and Science 2005, 45 (11), 1515-1521.
43.Sanchez, J. M.; Hidalgo, M.; Valiente, M.; Salvadóe, V. New macroporous polymers for the selective adsorption of gold (III) and palladium (II). I. The synthesis, characterization, and effect of spacers on metal adsorption. Journal of Polymer Science, Part A: Polymer Chemistry 2000, 38 (2), 269-278.
44.Sánchez, J. M.; Hidalgo, M.; Salvadó, V. Selective adsorption of gold (III) and palladium (II) on new phosphine sulphide-type chelating polymers bearing different spacer arms. Equilibrium and kinetic characterization. Reactive and Functional Polymers 2001, 46 (3), 283-291.
45.Ji, C.; Song, S.; Wang, C.; Sun, C.; Qu, R.; Wang, C.; Chen, H. Preparation and adsorption properties of chelating resins containing 3-aminopyridine and hydrophilic spacer arm for Hg(II). Chemical Engineering Journal 2010, 165 (2), 573-580.
46.Song, S.; Ji, C.; Wang, M.; Wang, C.; Sun, C.; Qu, R.; Wang, C.; Chen, H. Adsorption of silver(I) from aqueous solution by chelating resins with 3-aminopyridine and hydrophilic spacer arms: Equilibrium, kinetic, thermodynamic, and mechanism studies. Journal of Chemical and Engineering Data 2011, 56 (4), 1001-1008.
47.Diniz, C. V.; Doyle, F. M.; Ciminelli, V. S. Effect of pH on the adsorption of selected heavy metal ions from concentrated chloride solutions by the chelating resin Dowex M-4195. Separation Science and Technology 2002, 37 (14), 3169-3185.
48.Nagib, S.; Inoue, K.; Yamaguchi, T.; Tamaru, T. Recovery of Ni from a large excess of Al generated from spent hydrodesulfurization catalyst using picolylamine type chelating resin and complexane types of chemically modified chitosan. Hydrometallurgy 1999, 51 (1), 73-85.
49.Gao, J.; Liu, F.; Ling, P.; Lei, J.; Li, L.; Li, C.; Li, A. High efficient removal of Cu (II) by a chelating resin from strong acidic solutions: Complex formation and DFT certification. Chemical engineering journal 2013, 222, 240-247.
50.Parr, R. G., Density functional theory. Annual Review of Physical Chemistry 1983, 34 (1), 631-656.
51.Huang, J.; Zheng, Y.; Luo, L.; Feng, Y.; Zhang, C.; Wang, X.; Liu, X. Facile preparation of highly hydrophilic, recyclable high-performance polyimide adsorbents for the removal of heavy metal ions. Journal of hazardous materials 2016, 306, 210-219.
52.Wang, R.; Men, J.; Gao, B. The adsorption behavior of functional particles modified by polyvinylimidazole for Cu (II) ion. Clean–Soil, Air, Water 2012, 40 (3), 278-284.
53.Tekin, K.; Uzun, L.; Şahin, Ç. A.; Bektaş, S.; Denizli, A. Preparation and characterization of composite cryogels containing imidazole group and use in heavy metal removal. Reactive and Functional Polymers 2011, 71 (10), 985-993.
54.Soleimani, B.; Taghavi, M.; Ghaemy, M. Synthesis, characterization and heavy metal ion adsorption behavior of imidazole-based novel polyamides and polyimides. Journal of the Mexican Chemical Society 2017, 61 (3), 229-240.
55.Chen, J.-C.; Wu, J.-A.; Li, S.-W.; Chou, S.-C. Highly phenylated polyimides containing 4,4'-diphenylether moiety. Reactive and Functional Polymers 2014, 78, 23-31.
56.Chen, J. C.; Liu, Y. T.; Leu, C. M.; Liao, H. Y.; Lee, W. C.; Lee, T. M. Synthesis and properties of organosoluble polyimides derived from 2, 2'‐dibromo‐and 2, 2', 6, 6'‐tetrabromo‐4, 4'‐oxydianilines. Journal of Applied Polymer Science 2010, 117 (2), 1144-1155.
57.Chen, J. C.; Wu, J. A.; Chang, H. W.; Lee, C. Y. Organosoluble polyimides derived from asymmetric 2‐substituted‐and 2, 2', 6‐trisubstituted‐4, 4'‐oxydianilines. Polymer international 2014, 63 (2), 352-362.
58.張惠雯, 「含不對稱結構的2-Bromo-與2,2',6-Tribromo-4,4'-Oxydianiline合成可溶性聚醯亞胺及其性質探討」, 碩士論文, 國立臺灣科技大學, 2011.
59.陳奕愷, 「由2,2'-bis(2,2'-bipyridinyl)-4,4'-oxydianiline合成聚醯亞胺及其性質探討」, 碩士論文, 國立臺灣科技大學, 2019.
60.Romero, F. M.; Ziessel, R. A straightforward synthesis of 5-bromo and 5, 5'-dibromo-2, 2'-bipyridines. Tetrahedron letters 1995, 36 (36), 6471-6474.
61.Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.; Larsen, R. D.; Reider, P. J. An improved protocol for the preparation of 3-pyridyl-and some arylboronic acids. The Journal of organic chemistry 2002, 67 (15), 5394-5397.
62.Cai, D.; Hughes, D. L.; Verhoeven, T. R. A study of the lithiation of 2, 6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010. Tetrahedron letters 1996, 37 (15), 2537-2540.
63.Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical reviews 1995, 95 (7), 2457-2483.
64.Yan, S.; Chen, W.; Yang, X.; Chen, C.; Huang, M.; Xu, Z.; Yeung, K. W.; Yi, C. Soluble polyimides based on a novel pyridine-containing diamine m, p-PAPP and various aromatic dianhydrides. Polymer Bulletin 2011, 66 (9), 1191-1206.
65.Larsen, J. W.; Freund, M.; Kim, K. Y.; Sidovar, M.; Stuart, J. L. Mechanism of the carbon catalyzed reduction of nitrobenzene by hydrazine. Carbon 2000, 38 (5), 655-661.
66.Cegłowski, M.; Schroeder, G. Removal of heavy metal ions with the use of chelating polymers obtained by grafting pyridine–pyrazole ligands onto polymethylhydrosiloxane. Chemical Engineering Journal 2015, 259, 885-893.
67.Ballal, D.; Chapman, W. G. Hydrophobic and hydrophilic interactions in aqueous mixtures of alcohols at a hydrophobic surface. The Journal of chemical physics 2013, 139 (11), 114706.
68.Soeno, T.; Inokuchi, K.; Shiratori, S. Ultra-water-repellent surface: fabrication of complicated structure of SiO2 nanoparticles by electrostatic self-assembled films. Applied Surface Science 2004, 237 (1), 539-543.
69.Saadeh, H. A.; Shairah, E. A. A.; Charef, N.; Mubarak, M. S. Synthesis and adsorption properties, toward some heavy metal ions, of a new polystyrene‐based terpyridine polymer. Journal of applied polymer science 2012, 124 (4), 2717-2724.