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研究生:蘇嘉榮
研究生(外文):Chia-Jung Su
論文名稱:溶媒對合成隱性有機顏料影響之研究
論文名稱(外文):The Study on the Effect of Solvent Properties in the Preparation of Latent Pigment from Diketopyrrole
指導教授:鄭文桐
學位類別:碩士
校院名稱:國立中興大學
系所名稱:化學工程學系所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2008
畢業學年度:96
語文別:中文
論文頁數:57
中文關鍵詞:隱性顏料溶劑效應有機顏料咯並吡咯二酮顏料
外文關鍵詞:Latent pigmentSolvent effectorganic pigmentdiketopyrrolopyrrole
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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.
目 錄

中文摘要-------------------------------------------------I
英文摘要-------------------------------------------------II
目錄 ----------------------------------------------------III
表目錄 --------------------------------------------------V
圖目錄 --------------------------------------------------VI
第一章 緒論 --------------------------------------------1
1-1 前言 -----------------------------------------------1
1-2 研究目的--------------------------------------------2
1-3 研究方法--------------------------------------------3
1-4 本論文架構------------------------------------------4
第二章 文獻回顧與研究動機 ------------------------------5
2-1 有機顏料的定義--------------------------------------5
2-2 有機顏料和染料的差異--------------------------------5
2-3 有機顏料的歷史與發展--------------------------------6
2-4 有機顏料改質----------------------------------------9
2-4-1 隱性顏料合成--------------------------------------9
2-4-2 隱性顏料的應用------------------------------------10
2-5 研究動機--------------------------------------------13
第三章 實驗方法-----------------------------------------14
3-1 實驗材料與儀器設備----------------------------------14
3-1-1 實驗材料------------------------------------------14
3-1-2 實驗儀器與設備------------------------------------16
3-2 實驗方法--------------------------------------------17
3-2-1 材料製備------------------------------------------17
3-2-2 儀器原理與分析------------------------------------19
第四章 結果與討論---------------------------------------25
4-1 隱性顏料Boc-DPP合成之確認---------------------------25
4-2 改質後隱性顏料Boc-DPP純化---------------------------27
4-3 溶媒對合成隱性顏料的影響----------------------------32
4-3-1 前處理的影響--------------------------------------32
4-3-2 極性與分子體積的影響------------------------------36
4-3-3 改質條件的影響------------------------------------38
4-3-4 改質選擇性的探討----------------------------------42
4-4 隱性顏料的加熱還原----------------------------------47
第五章 綜合結論與未來延續方向---------------------------53
5-1 綜合結論--------------------------------------------53
5-2 未來延續方向----------------------------------------54
參考文獻------------------------------------------------55

表 目 錄

表3-2-1-1有機顏料與改質劑的當量-------------------------18
表4-3-2-1溶劑的極性與分子體積---------------------------37

圖目錄

圖1-3-1 研究流程圖----------------------------------------3
圖2-4-1 顏料DPP與隱性顏料相互轉化示意圖-------------------9
圖3-2-2-1 傅利葉紅外線光譜分析儀原理示意圖----------------20
圖4-1-1 改質前顏料DPP與改質後隱性顏料Boc-DPP的IR光譜圖----26
圖4-1-2 隱性顏料Boc-DPP的1H-NMR光譜圖---------------------26
圖4-2-1 Chloroform系統產物純化次數為0時的1H-NMR光譜圖-----29
圖4-2-2 Chloroform系統產物純化次數為10時的1H-NMR光譜圖----29
圖4-2-3 Chloroform系統產物純化次數為15時的1H-NMR光譜圖----29
圖4-2-4 THF系統產物純化次數為0時的1H-NMR光譜圖------------30
圖4-2-5 THF系統產物純化次數為10時的1H-NMR光譜圖-----------30
圖4-2-6 THF系統產物純化次數為15時的1H-NMR光譜圖-----------30
圖4-2-7 PGMEA系統產物純化次數為0時的1H-NMR光譜圖----------31
圖4-2-8 PGMEA系統產物純化次數為15時的1H-NMR光譜圖---------31
圖4-2-9 PGMEA系統產物純化次數為20時的1H-NMR光譜圖---------31
圖4-3-1-1 顏料DPP前處理1小時的平均二次粒徑分佈圖----------33
圖4-3-1-2 顏料DPP前處理2小時的平均二次粒徑分佈圖----------33
圖4-3-1-3 顏料DPP前處理3小時的平均二次粒徑分佈圖----------34
圖4-3-1-4 顏料DPP前處理4小時的平均二次粒徑分佈圖----------34
圖4-3-1-5 顏料DPP前處理5小時的平均二次粒徑分佈圖----------35
圖4-3-1-6 平均二次粒徑對隱性顏料Boc-DPP回收率的影響-------35
圖4-3-2-1 隱性顏料Boc-DPP在三種不同溶劑下的回收率分佈圖---37
圖4-3-3-1 chloroform系統改質時間的紫外光譜圖--------------40
圖4-3-3-2 THF系統改質時間的紫外光譜圖---------------------40
圖4-3-3-3 PGMEA系統改質時間的紫外光譜圖-------------------40
圖4-3-3-4 chloroform系統改質後顏料DPP溶於溶劑的紫外光譜圖-41
圖4-3-3-5 THF系統改質後顏料DPP溶於溶劑的紫外光譜圖--------41
圖4-3-3-6 PGMEA系統改質後顏料DPP溶於溶劑的紫外光譜圖------41
圖4-3-4-1 Chloroform系統隱性顏料Boc-DPP的1H-NMR光譜圖-----44
圖4-3-4-2 Chloroform系統隱性顏料Boc-DPP在空氣環境下,以10℃/min的升溫速率從50到350℃的熱重分析-------------------44
圖4-3-4-3 THF系統隱性顏料Boc-DPP的1H-NMR光譜圖------------45
圖4-3-4-4 THF系統隱性顏料Boc-DPP在空氣環境下,以10℃/min的升溫速率從50到350℃的熱重分析-------------------------------45
圖4-3-4-5 PGMEA系統隱性顏料Boc-DPP的1H-NMR光譜圖----------46
圖4-3-4-6 PGMEA系統隱性顏料Boc-DPP在空氣環境下,以10℃/min的升溫速率從50到350℃的熱重分析-----------------------------46
圖4-4-1 隱性顏料Boc-DPP加熱後產物的紅外光譜圖-------------49
圖4-4-2 顏料DPP、隱性顏料Boc-DPP及隱性顏料Boc-DPP加熱後產物的紫外光譜圖----------------------------------------------49
圖4-4-3 顏料DPP和隱性顏料Boc-DPP於甲苯的溶解情形----------50
圖4-4-4 隱性顏料Boc-DPP於樹脂中在加熱120℃下隨著時間變化的實物圖,(1) 0分鐘、(2) 15分鐘、(3) 60分鐘-------------------50
圖4-4-5 隱性顏料Boc-DPP於樹脂薄膜中在加熱120℃,隨時間變化的紫外光譜圖------------------------------------------------51
圖4-4-6 隱性顏料Boc-DPP於樹脂薄膜中加熱還原的粒子分佈FESEM圖--------------------------------------------------------52
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