研究生: |
翁郁雯 Yu-Wen Weng |
---|---|
論文名稱: |
新型丙烯酸酯單體合成及其網狀聚合材料的性質探討 Synthesis of New Acrylate Monomer and Research for the Properties of Their Polymer Networks. |
指導教授: |
何郡軒
Jinn-Hsuan Ho |
口試委員: |
王孟菊
Meng-Jiy Wang 林文賓 Wen-Pin Lin |
學位類別: |
碩士 Master |
系所名稱: |
工程學院 - 化學工程系 Department of Chemical Engineering |
論文出版年: | 2020 |
畢業學年度: | 108 |
語文別: | 中文 |
論文頁數: | 117 |
中文關鍵詞: | 丙烯酸酯 、紫光固化材料 、網狀聚合 |
外文關鍵詞: | UV-Curable Material, Polymer Network |
相關次數: | 點閱:200 下載:0 |
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本論文主要是合成出不同碳鏈長度差異的一系列新型具甲基丙烯酸酯之光固化單體,單體合成透過甲基丙烯酸環氧丙酯具有環氧基團之結構可於鹼性環境下,將環氧基團開環和具有羧酸基團分子進行酯化反應,爾後針對新型光固化單體與其光固化後之材料進行性質的探討。利用數位式旋轉黏度計(Viscometer)、核磁共振光譜圖譜(NMR)鑑定單體合成之反應程度,接著加入光起始劑2-Hydroxy-2-methylpropiophenone(Irgacure-1173)1 並添加不同比例之交聯劑1,6-Hexanediol- diacrylate(HDDA)2照光聚合,利用差掃瞄熱分析儀(DSC)、接觸角測量儀、平均膨潤動力分析法與萬能材料試驗機,分析光固化後材料之熱穩定性、表面親疏水性、平均膨潤度與速率及機械強度等性質進行比較。
In this research, we synthesized a series of new acrylate monomer with different carbon chain lengths. Under basic conditions, the epoxide group of glycidyl methacrylate was opened and reacted with other monomers that have carboxylic acids with different carbon chain lengths by esterification. Used the nuclear magnetic resonance spectroscopy (NMR) to identify the structures of monomer. we used photoinitiator (2-Hydroxy-2-methylpropiophenone,Irgacure-1173) and different proportions of cross-linking agent (1,6-Hexanediol- diacrylate,HDDA) to cure with UV light,then analyzed their properties,such as viscosity, the degree of polymerization, mechanical strength, thermal stability, hydrophilicity or hydrophobicity on the surface, swelling ratio and swelling rate by viscometer, Universal Testing , DSC, Contact Angle and swelling test.
1. Moon, J. H., Shul, Y. G., Han, H. S., Hong, S. Y., Choi, Y. S., Kim, H. T., A study on UV-curable adhesives for optical pick-up: I. Photo-initiator effects. International Journal of Adhesion and Adhesives 2005, 25 (4), 301-312.
2. HO, C. S., WANG, W. T., Effect of Formulation on Properties of Polyester Acrylate Resins. Journal of Science and Engineering Technology 2017, 35(2), 33-43.
3. Ibech CC. Thermoplastic Materials: Properties,Manufacturing Methods and Applications. Boca Raton, FL.
4. Voller, L. M., Warshaw, E. M., Acrylates: new sources and new allergens. Clinical and Experimental Dermatology 2020, 45 (3), 277-283.
5. Jiang, Y., Pan, M., Yuan, J., Wang, J., Song, S., Liu, G., Fabrication and structural characterization of poly(vinylidene fluoride)/polyacrylate composite waterborne coatings with excellent weather resistance and room-temperature curing. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2020, 598.
6. Liska, R.; Schwager, F.; Maier, C.; Cano-Vives, R.; Stampfl, J., Water-soluble photopolymers for rapid prototyping of cellular materials. Journal of Applied Polymer Science 2005, 97 (6), 2286-2298.
7. Abdel-Wakil, W., A new route for synthesis of polyurethane vinyl acetate acrylate emulsions as binders for pigment printing of cotton fabrics. Egyptian Journal of Chemistry 2020, 63 (3), 1063-1073.
8. Lakhera, N., Graucob, A., Schneider, A. S., Kroner, E., Arzt, E., Yakacki, C. M., Frick, C. P., Effect of viscoelasticity on the spherical and flat adhesion characteristics of photopolymerizable acrylate polymer networks. International Journal of Adhesion and Adhesives 2013, 44, 184-194.
9. Punyani, S., Deb, S., Singh, H., Contact killing antimicrobial acrylic bone cements: preparation and characterization. Journal of Biomaterials Science, Polymer Edition 2012, 18 (2), 131-145.
10. Elliott J. E., Lovell L.G., Bowman C.N., Primary cyclization in the polymerization of bis-GMA and TEGDMA: a modeling approach to understanding the cure of dental resins. Dental Materials, 2001, 17,221-229.
11. Lu, H., Stansbury, J. W., Nie, J., Berchtold, K. A.; Bowman, C. N., Development of highly reactive mono-(meth)acrylates as reactive diluents for dimethacrylate-based dental resin systems. Biomaterials 2005, 26 (12), 1329-36.
12. Nagai, K, New developments in the production of methyl methacrylate. Appl. Catal. A Gen. 2001, 221, 367–377.
13. Fischer .E., Arthur Speier. Darstellung der Ester. Chemische Berichte. 1895, 28,
3252–3258.
14. Salaklang, J., Maes, V., Conradi, M., Dams, R., Junkers, T., Direct synthesis of acrylate monomers in heterogeneous continuous flow processes. Reaction Chemistry & Engineering 2018, 3 (1), 41-47.
15. Twibanire, J. A. K., and Grindley, T. B., Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents. Org. Lett. 2011, 13 (12), 2988-2991.
16. Sun, L., Zhu, L., Xue, W., Zeng, Z., Kinetics of p-toluene-sulfonic acid catalyzed direct esterification of pentaerythritol with acrylic acid for pentaerythritol diacrylate production. Chemical Engineering Communications 2019, 207 (3), 331-338.
17. Niesbach, A., Fuhrmeister, R., Keller, T., Lutze, P., Górak, A., Esterification of Acrylic Acid and n-Butanol in a Pilot-Scale Reactive Distillation Column—Experimental Investigation, Model Validation, and Process Analysis. Industrial & Engineering Chemistry Research 2012, 51 (50), 16444-16456.
18. Sert, E.; Atalay, F. S., n-Butyl acrylate production by esterification of acrylic acid with n-butanol combined with pervaporation. Chemical Engineering and Processing: Process Intensification 2014, 81, 41-47.
19. Robert Thornton Morrison. Robert Neilson Boyd (民 81)有機化學1﹑2。台北:東華
20. Hui, G., Huang, W., Song, Y., Chen, D., Zhong, A., Synthesis and characterization of acrylate copolymer containing fluorescein functional group. Korean Journal of Chemical Engineering 2013, 30 (8), 1609-1613.
21. Neises B., Steglich W.. Simple Method for the Esterification of Carboxylic Acids. Angew. Chem. Int. Ed. 1978, 17, 522–524.
22. Ashjari, H. R., Ahmadi, A., Dorraji, M. S. S., Synthesis and employment of PEGDA for fabrication of superhydrophilic PVDF/PEGDA electrospun nanofibrous membranes by in-situ visible photopolymerization. Korean Journal of Chemical Engineering 2017, 35 (1), 289-297.
23. Ali, S., Cuchiara, M. L., West, J. L., Micropatterning of poly(ethylene glycol) diacrylate hydrogels. Methods Cell Biol 2014, 121, 105-19.
24. Salaklang, J., Maes, V., Conradi, M., Dams, R., Junkers, T., Direct synthesis of acrylate monomers in heterogeneous continuous flow processes. Reaction Chemistry & Engineering 2018, 3 (1), 41-47.
25. Evans S. B., Mulvaney J. E., Hall, Jr. H. K., On the Synthesis of Pure (Meth) acrylate Esters and Their Corresponding Homopolymers. J Polym Sci A Polym Chem 1990, 28, 1073-1078
26. Acik, G., Karatavuk, A. O., Synthesis, properties and biodegradability of cross-linked amphiphilic Poly(vinyl acrylate)-Poly(tert-butyl acrylate)s by photo-initiated radical polymerization. European Polymer Journal 2020, 127.
27. Moreno, M., Goikoetxea, M., Barandiaran, M. J., Biobased-waterborne homopolymers from oleic acid derivatives. Journal of Polymer Science Part A: Polymer Chemistry 2012, 50 (22), 4628-4637.
28. Jung, J., Choi, H., Hong, S., Yoon, S. J., Kim, T.-H., Lee, J. Y., Hong, Y. T., So, S., Surface-initiated ATRP of glycidyl methacrylate in the presence of divinylbenzene on porous polystyrene-based resins for boron adsorption. Desalination 2020, 473.
29. Chen1, J., Park K., Synthesis of fast-swelling, superporous sucrose hydrogels. Carbohydrate Polymers 2000, 41,259–268
30. Feng, Y., Hu, J., Wang, F., Huang, Q., Peng, C., Xu, Z., Synthesizing promising epoxy acrylate prepolymers applied in ultraviolet cured adhesives based on esterification reaction. Materials Research Express 2018, 5 (6).
31. Huang, W. T.; He, G. J.; Tang, W. D.; Cao, X. W., Ultraviolet‐induced chain extension of poly(ethylene terephthalate) based on radical reaction with the aid of trimethylolpropane triacrylate and glycidyl methacrylate during extrusion. Polymer International 2020, 69 (7), 611-618.
32. Ferreiraa, L., Vidala, M.M., Geraldesb, C.F.G.C., Gila M.H., Preparation and characterisation of gels based on sucrose modified with glycidyl methacrylate. Carbohydrate Polymers 2000, 41, 15–24.
33. Altintas, E. B., Turkmen, D., Karakoc, V., Denizli, A., Hemoglobin binding from human blood hemolysate with poly(glycidyl methacrylate) beads. Colloids Surf B Biointerfaces 2011, 85 (2), 235-40.
34. Erol, K., Uzunoglu, A., Kose, K., Sarica, B., Avci, E., Kose, D. A., Synthesis and characterization of Ag(+)-decorated poly(glycidyl methacrylate) microparticle design for the adsorption of nucleic acids. J Chromatogr B Analyt Technol Biomed Life Sci 2018, 1081-1082, 1-7.
35. Xiong, C., Wang, S., Zhang, L., Li, Y., Zhou, Y., Peng, J., Selective recovery of silver from aqueous solutions by poly (glycidyl methacrylate) microsphere modified with trithiocyanuric acid. Journal of Molecular Liquids 2018, 254, 340-348.
36. Galhoum, A. A., Elshehy, E. A., Tolan, D. A., El-Nahas, A. M., Taketsugu, T., Nishikiori, K., Akashi, T., Morshedy, A. S., Guibal, E., Synthesis of polyaminophosphonic acid-functionalized poly(glycidyl methacrylate) for the efficient sorption of La(III) and Y(III). Chemical Engineering Journal 2019, 375.
37. Karahan, O., Aydin, K., Edizer, S., Odabasi, N., Avci, D., Development of reactive methacrylates based on glycidyl methacrylate. Journal of Polymer Science Part A: Polymer Chemistry 2010, 48 (17), 3787-3796.
38. Cole, M. A., Jankousky, K. C., Bowman, C. N., Redox Initiation of Bulk Thiol-Ene Polymerizations. Polym Chem 2013, 4 (4), 1167-1175.