Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/3609
標題: 溶媒對合成隱性有機顏料影響之研究
The Study on the Effect of Solvent Properties in the Preparation of Latent Pigment from Diketopyrrole
作者: 蘇嘉榮
Su, Chia-Jung
關鍵字: Latent pigment;溶劑效應;Solvent effect;organic pigment;diketopyrrolopyrrole;有機顏料;吡咯並吡咯二酮顏料
出版社: 化學工程學系所
引用: 1.沈永嘉, “有機顏料–品種與應用”, 化學工業出版社, 1–10, 2001. 2.Temple C. Patton, “Pigment Handbook, vol. Ⅲ, Characterization and Physical Relationships”, A Wiley–Interscience Publication, 157–167, 1973. 3.Peter A. LEWIS, “Pigment Handbook, vol. Ⅰ, Properties and Economics” , A Wiley–Interscience Publication, 519–534, 1987. 4.Temple C. Patton , “Pigment Handbook, vol. Ⅱ, Application and Market”, A Wiley–Interscience Publication, 163–203, 1973. 5.Gu G. L., Wu S. L., “Art of Pigment”, Chemical Industrial Inc. Publication, 315–378, 1996. 6.ITRIUC-0267-T202(88), “ Marketing Analysis of Dyes & Pigments Industry in 1999 ”, ITRI, 1999. 7.Temple C. Patton, “ Pigment Handbook, vol. Ⅰ, Properties and Economics”, A Wiley–Interscience Publication, 493–504, 1973. 8.Heinrich Zollinger, “ Color Chemistry, Syntheses, Properties and Applications of Organic Dyes and Pigment”, New York :VCH Publisher Inc., 85–144, 1987. 9.H.A. Lubs, “ The Chemistry of Synthetic Dyes and Pigments”, American Chemical Society Publication, 662–679, 1955. 10.Hans F. Ebel, Christina Dyllick-Brenzinger, “Color Chemistry Syntheses, Properties and Applications of Organic Dyes and Pigment”, New York:CVH Publisher Inc., 1–7, 1987. 11.Olof Wallquist, R. Lenz, “20 Years of DPP Pigments – Future Perspectives”, Macromol. Symp., 187, 617–629, 2002. 12.Ulrich Schadeli, John S. Zambounis, Abul Iqbal, Zhimin Hao, Henri Dubas, “Compositions for making structured color images and application thereof”, Eur. Patent:0654711, 1995. 13.John S. Zambounis, Zhimin Hao, Abul Iqbal, “Latent pigments activated by heat” Nature, 388, 131–132, 1997. 14.Kunihiro Ichimura, Koji Arimitsub and Masaru Tahara, “Photoacid-catalysed pigmentation of dyestuff precursors enhanced by acid amplifiers in polymer film”, J. Mater. Chem., 14, 1164–1172, 2004. 15.Shirong Wang, Xianfeng Liu, Jinqiu Xiao, Bing Liu, “A study on the application behaviors of latent pigment”, Dyes and Pigments, 61, 99–102, 2004. 16.John S. Zambounis, Zhimin Hao, Abul Iqbal, “Pyrrolo [3 ,4-C] pyrroloes”, U.S. Patent:5484943, 1996. 17.Olof Wallquist, Zhimin Hao, Abul Iqbal, “Mixed crystals and solid solution of 1,4-diketopyrrololen”, Eur. Patent:0704497, 1996. 18.Viresh H R, Cava M P. “Thermolytic remove of t-butyloxycar-bonyl (BOC) protecting group on indoles and pyrroles”, Tetra-hedron Letters, 26, 6141–6142, 1985. 19.劉冰, 王世榮, 肖金秋, “顏料改性的新技術-隱顏料技術”, chemical industry and engineering progress, 第21卷第一期, 20–22, 2002. 20.O. Phanstiel, Q. X. Wang, D. H. Powell, M. P. Ospina, B. A. Leeson, “Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes”, J. Org. Chem., 64, 803–806, 1999. 21.John Zambounis, Manfred Hofmann, “Structured pigment coating and its preparation and use”, U.S. Patent:5840449, 1998. 22.Werner Sieber, Veronique Hall-Goulle, “Process for preparing fine pigment dispersions”, U.S. Patent:6071989, 2000. 23.Johannes Legus, Zhimin Hao, Abul Iqbal, “Reactive extrusion of latent pigments”, U.S. Patent:6160037, 2000. 24.Ulrich Schadeli, John S. Zambounis, Abul Iqbal, Zhimin Hao, “Compositions for making structured color images and application thereof”, U.S. Patent:5879855, 1999. 25.Ulrich Schadeli, John S. Zambounis, Abul Iqbal, Zhimin Hao, Henri Dubas, “Compositions for making structured color images and application thereof”, U.S. Patent:6040108, 2000. 26.Ulrich Schadeli, Eric Tinguely, Veronique Hall-Goulle, Heinz Wolleb, Zhimin Hao, Abul Iqbal, “Highly transparent, color-pigmented high molecular weight material”, U.S. Patent:6120944, 2000. 27.Nobuo Suzuki, Koji Inoue, Naoki Kato, “Photosensitive colored composition for color filter”, U.S. Patent:6140016, 2000. 28.Dennis P Parazak, “Ink-jet inks comprising pigment precursors”, U.S. Patent:6102996, 2000. 29.林敬二, “儀器分析”, 美亞書版股份有限公司, p.372, 1995. 30.林正雄, “粒徑分析儀(上)”, 科儀新知, 20(2), p.6, 1998. 31.林正雄, “粒徑分析儀(下)”, 科儀新知, 20(3), p.41, 1998. 32.詹德均, “以氧離子束輔助磁控濺鍍光學薄膜之研究”,國立中央大學博士論文, p.44, 2004. 33.林智仁, “材料分析技術專題”, 工業材料雜誌, NO.184, 93-95, 2002. 34.Y. Marcus, “The properties of solvents”, John Wiley and Sons Ltd, 85–154, 1999.
摘要: 
目前有機顏料作為著色劑被廣泛的應用在塗料、塑膠、印刷油墨及電子工業上。有機顏料和染料不一樣的地方是有機顏料沒辦法溶解在溶劑裡,而染料可以容易地溶解在溶劑並且可進行均勻的染色應用;有機顏料的應用則需要消耗大量的時間和能量在顏料分散的步驟。隱性顏料可以將溶解性和分散性差的顏料改質成溶解性佳具染料性質之隱性顏料。使其在介質間達到均勻分散之效果,並用加熱還原法始隱性顏料還原成母體顏料。
由文獻可知一般改質方法回收率過低,故提高隱性顏料的回收率以提高其應用性為本研究之目的。由於溶劑對顏料分散之穩定度及化學改質反應是ㄧ重要因素,故本研究針對不同溶劑的極性及體積大小和其對顏料分散的穩定度對改質回收率的影響做ㄧ系統之討論。本研究所選用的溶劑包含下列三種:chloroform、Tetrahydrofuran(THF)、Propylene glycol monomethyl ether acetate(PGMEA)。此三種溶劑的極性以chloroform最大,THF次之,PGMEA最小;而分子體積則以PGMEA最大,THF次之,chloroform最小;在溶劑對顏料分散之穩定性方面,以chloroform最佳,THF次之,PGMEA最差。實驗結果顯示,隨著溶劑對顏料分散的穩定性增加及其極性增加、分子體積較小可以有效地增加隱性顏料Boc-DPP的回收率。此外,隱性顏料Boc-DPP分散於壓克力型樹脂(acrylate type binder)中時,可經由加熱方式還原成母體顏料DPP,藉由SEM分析結果顯示,其還原成之母體顏料的粒子於薄膜中可分散均勻,粒徑約30~50 nm。

Organic pigments are used as colourants in paints, plastics, printing inks, and electronics industries. Organic pigments are insoluble in solvent, whereas dyes can easily be dissolved in solvent as uniform coloring agents. The technology of “latent pigments” can crucially improve dispersion process. This technique enables to make the convention pigment into latent pigments with properties similar to dyes which are soluble in organic solvents. The latent pigments can be transformed to the parent pigment by thermal treatment.
The purpose of this study is to improve the recovery yield of making latent pigments. Because the the dispersive stability and chemical modification is an important factor, this study emphasize on the issues of latent pigment recovery yield, product polarity, molecular volume, and dispersive stability in solvents. Three solvents, chloroform, tetrahydrofuran (THF); and Propylene glycol monomethyl ether acetate (PGMEA) have been studied. The relative polarity of three solvents is chloroform>THF>PGMEA; the magnitude of molecular volume is PGMEA>THF>chloroform; and the degree of dispersive stability is chloroform>THF>PGMEA. The results show the recovery yield of Boc-DPP latent pigment increases with fine dispersive stability, high polarity, and low molecular volume of solvent. In addition, the Boc-DPP can be converted back to DPP by thermal process in acrylate resin. After the dispersion procedures, the DPP pigment are found to be well-dispersed in the membrane, and the particle size is about 30~50 nm by FESEM.
URI: http://hdl.handle.net/11455/3609
其他識別: U0005-0502200814155400
Appears in Collections:化學工程學系所

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