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研究生: 張為舟
Wei-Chou Chang
論文名稱: 雙雜環單偶氮及雙偶氮染料之合成及性質探討
Synthesis and Properties of Bisheterocyclic Mono and Disazo Dyes based on 5-Amino-3-Methyl- Pyrazole Compound
指導教授: 王英靖
Ing-Jing Wang
口試委員: 許應舉
Ying-Gev Hsu
陳耿明
Keng-Ming Chen
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: 2006
畢業學年度: 94
語文別: 中文
論文頁數: 62
中文關鍵詞: 3-胺基丁烯腈苯騈噻唑吡唑
外文關鍵詞: 3-aminocrotononitrile, bezothiazole, pyrazole
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雙雜環單偶氮及雙偶氮染料之合成及性質探討
張為舟 王英靖
中文摘要
本研究以2-胺基-6-取代基-苯騈噻唑(1a、1b)為起始物,在硫酸與亞硝酸鈉0~5℃冰浴的條件下與3-胺基丁烯腈偶合,合成中間體3a、3b,隨後與聯胺(4)水解縮合反應成不同的4-(6’-取代基-苯騈噻唑-偶氮基)- 5-胺基-3-甲基-吡唑中間體(5a、5b)。緊接著分成兩條路徑進行,一方面與4-取代基-苯醛(6a~6c)在鹼的催化條件下,脫水反應成5-(4’-取代基-苯亞烯胺)-4-(6’-取代基-苯騈噻唑-偶氮基)-3-甲基-吡唑(7a~7f);另一條路徑則與4-取代基-苯環(8a~8c),在弱酸下偶合成5-(4’-取代基-苯偶氮基)-4-(6’-取代基-苯騈噻唑-偶氮基)-3-甲基-吡唑染料(9a~9f)。所合成之化合物均經TLC、FT-IR及1H-NMR等鑑定確定其化學構造。

關鍵字: 苯騈噻唑,3-胺基丁烯腈,吡唑


Synthesis and Properties of Bisheterocyclic Mono and Disazo Dyes based on 5-Amino-3-Methyl- Pyrazole Compound
Wei-Chou Chang,Ing-Ging Wang
ABSTRACT
In this study,5-amino-3-methyl-4-(6’-substituted-bezothiazol-ylazo)-pyrazole compounds have been synthesized by the
cyclocondensation reaction of 2-(2’-hydrozone-3’-ketimino-
butyro-nitrile)-6-substituted-benzothiazole with hydrazine
hydrate.The dyes were dehydrated with 4-substituted-benzal
-dehyde to give 5-(4’-substituted-benzylideneamino)-4-(6’-sub-stituted benzothiazolylazo)-3-methyl-pyrazole,and obtained 5-(4’-substituted-phenylazo)-4-(6’-substituted-benzothiazolylazo)-3-methyl-pyrazole by coupled with 4-substituted-benzene.
The structures of these compounds were determined by
spectrometry of FT-IR and 1H-NMR etc. We also research
in wavelength of bisheterocyclic mono and disazo dyes.
Keywords: bezothiazole,3-aminocrotononitrile,pyrazole

目錄 中文摘要 I ABSTRACT II 圖表目錄 1 第1章 實驗 6 1-1 實驗藥品 6 1-2 實驗儀器 7 1-3 合成方法 8 1-3-1 2-(2’-Hydrozone-3’-ketimino-butyronitrile)-6- substituted-benzothiazole之合成(3a、3b) 8 1-3-2 雜環單偶氮染料(Heterocyclic monoazo dyes) (5a-5b)之合成 9 1-3-3 5-(4’-substituted-benzylideneamino)-4-(6’-substituted- benzothiazolylazo)-3-methyl-pyrazole之合成(7a~7f) 10 1-3-4 雜環雙偶氮染料之合成(9a~9f) 13 第2章 結果與討論 16 2-1 化合物3a、3b之合成及光譜分析 16 2-1-1 化合物3a、3b之物理數據 16 2-1-2 化合物3a、3b之光譜數據分析 17 2-2 雜環單偶氮染料(Heterocyclic monoazo dyes) (5a、5b)之合成及光譜分析 19 2-2-1 化合物5a、5b之合成 19 2-2-2 化合物5a、5b的物理實驗數據及光譜數據分析 20 2-2-2-1 化合物5a、5b的UV光譜數據分析 22 2-3 化合物7a-7f及9a-9f之合成及光譜分析 23 2-3-1 5-(4’-取代基-苯亞烯胺)-4-(6’-取代基-苯騈噻唑-偶氮基)-3-甲基-吡唑(7a-7f)之合成 23 2-3-2 5-(4’-取代基-苯偶氮基)-4-(6’-取代基-苯騈噻唑-偶氮 基)-3-甲基-吡唑(9a-9f) 之合成 24 2-3-3 化合物7a-7f及9a-9f的物理實驗數據及光譜數據分析 25 2-3-3-1 化合物7a-7f及9a-9f的UV吸收光譜數據分析 ………………………………………………….38 第三章 結論 44 第四章 參考文獻 46

第四章 參考文獻

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