跳到主要內容

簡易檢索 / 詳目顯示

研究生: 張榮宗
Jung-Tsung Chang
論文名稱: 2-胺基噻吖唑衍生物合成與其性質之探討
指導教授: 郭坤土
Kung-Tu Kuo
王天財
Ten-Tsai Wang
口試委員:
學位類別: 碩士
Master
系所名稱: 工學院 - 化學工程與材料工程學系
Department of Chemical & Materials Engineering
畢業學年度: 93
語文別: 中文
論文頁數: 87
中文關鍵詞: 噻吖唑偶氮染料吖次甲基染料
外文關鍵詞: azamethine, azo dyes, thiazole
相關次數: 點閱:12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
  • 本研究以酮類化合物與硫尿及碘反應合成五種2-胺基噻吖唑衍生物,並藉由其IR光譜圖來討論各官能基於圖譜上顯示之吸收峰來判斷此類化合物之形成。以2-胺基-4-苯基-1,3-噻吖唑為原料,該化合物之胺基重氮化與二甲基苯胺及γ酸偶合為偶氮染料,也與對二甲基胺苯甲醛在酸性乙醇下反應為吖次甲基染料兩大類。將所合成之染料與苯系染料比較,觀察其可見光譜之最大吸收波長之異同,所得結果噻吖唑系都有紅移現象。其中偶氮染料系在酸性溶液中紅移3~ 77 nm;在鹼性溶液中有沉澱現象,因此有些不能比較;吖次甲基類染料則紅位移波長達267及237 nm。


    The five derivatives of 2-aminothiazoles were obtained by reacting with ketone compounds and thiourea, iodine, and identified these com- pound with their several functional groups absorption peak of the IR spectra. Synthesis azo dyes were synthesized from amine of the 2-amino- 4-phenyl-1,3-thiazole diazotize to coupling with N,N-dimethylaniline or gamma acid, also reacted with the 4-Dimethylaminobenzaldehyde to form the azamethine dyes in the acid ethanol solution. Compare and observe the difference between thaizole’s dyestuffs and benzene’s dyestuffs there maximum of the absorptive wavelengths of the visible light, the result of the thaizole’s dyestuffs has been shown the bathochromic shift effect be- tween 3~77 nm in the acid solution, there is phenomenon of precipitating in the base solution, so some can''t compare; but azamethine dyestuffs ba- thochromic shift 267 and 237 nm.

    摘要------------------------------------------------------------------------Ⅰ Abstract--------------------------------------------------------------------Ⅱ 目錄------------------------------------------------------------------------Ⅲ 圖目錄----------------------------------------------------------------------Ⅴ 表目錄----------------------------------------------------------------------Ⅷ 第一章 緒論----------------------------------------------------------------1 第二章 文獻回顧------------------------------------------------------------5 第三章 實驗部分------------------------------------------------------------8 3-1 實驗儀器、藥品------------------------------------------------------8 3-2 合成流程-----------------------------------------------------------11 3-3 實驗步驟-----------------------------------------------------------14 第四章 結果與討論---------------------------------------------------------31 4-1 合成結果----------------------------------------------------------------31 4-2 結果討論----------------------------------------------------------------39 4-2-1 2-胺基-1,3-

    [1]郭惠宜, “植物性染料與金屬化合物染著棉纖維之色彩變化”,逢甲大學紡織工程研究所碩士論文,九十三年。
    [2]http://ttf.textiles.org.tw/news/cm92070403.htm
    [3]蔡弼丞, “吡唑[1,5-a]嘧啶系列衍生物之合成及性質探討”,國立台灣科技大學高分子工程研究所碩士論文,九十三年。
    [4]蕭伊伶, “吡酮雜環偶氮染料合成及其性質之研究”,國立台灣科技大學高分子工程研究所碩士論文,九十三年。
    [5]吳育松, “N-胺基-2-吡酮衍生物之合成及性質探討”,國立台灣科技大學高分子工程研究所碩士論文,九十年。
    [6]http://www.chemicalland21.com/arokorhi/specialtychem/finechem/2-AMINO-4-METHYLTHIAZOLE.htm
    [7]H. L. Liu, Z. C. Li and T. Anthonsen, “Synthesis and Fungicidal Ac- tivity of 2-Imino-3-(4-Arylthiazol-2-yl)-Thiazolidin-4-Ones and Their 5-Arylidene Derivatives”, Molecules, 5, 1055-1061(2000).
    [8]宋建宏, “單金屬配位含氫鍵引力之四分子盤狀液晶”,國立中央大學化學研究所碩士論文,八十九年。
    [9]小西謙三,黑木宣彥,“工業合成染料化學”,復漢出版,p.127. (1994)
    [10]The Society of Dyers and Colourists, “Color Index”, 3rd ed., vol.4, p.4154(1971).
    [11]陳姍玗, “偶氮染料褪色程序之開發與生態工程之探討”,逢甲大學化學工程研究所碩士論文,八十九年。
    [12]The Society of Dyers and Colourists, “Color Index”, 3rd ed., vol.4, p.4277(1971).
    [13]張俊雄, “ 含金屬偶氮染料之合成與性質之研究”,國立中央大學化工所碩士論文,八十二年。
    [14]陳彥達, “2-(4-胺基苯偶氮)-7-胺基-1-羥基-3-奈磺酸之合成研究”, 國立中央大學化工所碩士論文,八十三年。
    [15]黃茂村, “偶氮染料及其中間體合成的研究”, 國立中央大學化工所碩士論文,八十七年。
    [16]陳智能, “4,4''-雙胺基偶氮苯類化合物及其偶合染料之研究”, 國立中央大學化工所碩士論文,八十八年。
    [17]K. Venkataraman,”The Chemistry of Synthetic Dyes”,Vol. 3,p.281.(1970)
    [18]The Society of Dyers and Colourists, “Color Index”, 3rd ed., vol.4, p.4009,4094,4225(1971).
    [19]吳育松, “N-胺基-2-吡酮衍生物之合成及性質研究”, 國立台灣科技大學高分子工程研究所碩士論文,八十九年。
    [20]詹智揚, “氰基次甲基與氰基氮次甲基系衍生物之合成及其性質之研究”, 國立台灣科技大學高分子工程研究所碩士論文,九十一年。
    [21]邱永亮,魏盛德, “染色化學”,徐氏文教基金會,(2000),本論文中之化合物命名參考。
    [22]V. B. Kovalska, D. V. Kryvorotenko, A. O. Balanda, V. P. Tokar, M. Yu. Losytskyy, S. M. Yarmoluk, “Fluorescent Homodimer Styrylcya- nines: Synthesis and Spectral-luminescent Studies in Nucleic Acids and Protein Complexes”, Dyes and Pigments, 67, 47-54 (2005).
    [23]M. A. Metwally, E. Abdel-latif, A. M. Khalil, F. A. Amer, G. Kaupp, “New Azodisperse Dyes with Thiazole Ring for Dyeing Polyesterfa- brics”, Dyes and Pigments, 62, 181-195(2004)
    [24]G. Cilento, E. C. Miller, J. A. Miller, “On the Addition of Protons to Derivatives of 4-Aminoazobenzene”, J. Am. Chem. Soc., 78(8), 1718-1722(1956).
    [25]M. A. Abbady, Sh. H. Abdel-Hafez, M. M. Kandeel, M. I. Abdel- Monem, “Syntheses of New Unsymmetrical and Symmetrical Diarylsulphides and Diarylsulphones Containing Thiazolinyl and Thiazolidinonyl Moieties Using 4,4''-Diacetyldiphenylsulphide”, Molecules, 8, 622-641(2003).
    [26]Bruno Freitas Lira, Petrônio Filgueiras de Athayde Filho, Joseph Miller, Alfredo Mayall Simas, Aderson de Farias Dias, Maria Joaquina Vieira, “Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion”, Molecules, 7, 791-800(2002).
    [27]M. A. Metwally, E. Abdel-latif, F. A. Amer, G. Kaupp, “Synthesis of New 5-Thiazolyl Azo-disperse Dyes for Dyeing Polyester Fabrics”, Dyes and Pigments, 60, 249-264(2004).
    [28]W. S. McGUIRE, T. F. IZZO, SAVERIO ZUFFANTI, “The Structure of Protonated Molecules of Aminoazobenzene Derivatives”, J. Org. Chem., 21, 632-634(1956).
    [29]Alaaddin Cukurovali, Ibrahim Yilmaz, Habibe Ozmen, Misir Ahmedzade, “A New Mesitylenic Cyclobutane Substituted Schiff Base Ligand and its Co(II), Cu(II), Ni(II), and Zn(II) Complexes”, Heteroatom Chemistry, 12, 42-46(2001).
    [30]Alaaddin Cukurovalı, Ibrahim Yılmaz, Misir Ahmedzade, Sevda Kırbag, “Antimicrobial Activity Studies of the Metal Complexes Derived from Cyclobutane-Substituted Thiazole Carbamate Ligands”, Heteroatom Chemistry, 12, 665-670(2001).
    [31]Metin Koparır, Ahmet Cansız, Misir Ahmedzade, Ahmet Cetin, “Cy- clobutane-Substituted Diacetamido Sulfides and 2,5-Diacylthio- phenes”, Heteroatom Chemistry, 15, 26-31(2004).
    [32]Ibrahim Yilmaz, Alaaddin Cukurovali, “Salicylaldehyde Thiazolyl Hydrazones as Ligands”, Heteroatom Chemistry, 14, 617-621(2003).
    [33]Cengiz Soykan, Ibrahim Erol, Sevda Kırbag, “Synthesis and Charac- terization of Poly(1,3-thiazol-2-ylcarbomoyl) Methyl Methacrylate: Its Metal Complexes and Antimicrobial Activity Studies”, Journal of Applied Polymer Science, 90, 3244-3251(2003).
    [34]R. Salzmann, M. Wojdelski, M. McMahon, R. H. Havlin, E. Oldfield, “A Solid-State Nitrogen-15 Nuclear Magnetic Resonance Spectro- scopic and Quantum Chemical Investigation of Nitrosoarene-Metal Interactions in Model Systems and in Heme Proteins”, J. Am. Chem. Soc., 120, 1349-1356(1998).
    [35]Kyungsoon Kim, Hae-Yong Shin, “Bioreduction of N,N-dimethyl- p-nitrosoaniline”, Journal of Biochemistry and Molecular Biology, 34, 225-229(2001).
    [36]T. Konstantinova, P. Petrova, “On The Synthesis of some Bifunc- tional Reactive Triazine Dyes”, Dyes and Pigments, 52, 115-120(2002).
    [37]P. Petrova-Miladinova, T. N. Konstantinova, “On The Synthesis of some Reactive Triazine Azodyes Containing Tetramethylpiperidine Fragment”, Dyes and Pigments, 67, 63-69(2005).
    [38]Joon-Kyun Lee, Seong-il Um, Yonghan Kang, Dae-jin Baek, “The Synthesis and Properties of Asymmetrically Substituted 4,40-bis- (1,3,5-Triazin-6-yl)diaminostilbene-2,20-disulfonic Acid Derivatives as Fluorescent Brighteners”, Dyes and Pigments, 64, 25-30(2005).
    [39]M. Christoff, S. B. Yamaki, M. G. de Oliveira, T. D. Z. Atvars, “De- tection of Residual Acidic Groups in Several Poly(Nalkyl metha- crylate)s Using Photophysical and Photochemical Probes”, Journal of Applied Polymer Science, 92, 830-838(2004).
    [40]Ming Shien Yen, Ing Jing Wang, “A Facile Syntheses and Absorption Characteristics of some Monoazo Dyes in bis-Heterocyclic Aromatic Systems Part II: Syntheses of 4-(p-Substituted)phenyl-2-(2-pyrido- 5-yl and 5-pyrazolo-4-yl)azo-thiazole Derivatives”, Dyes and Pigments, 63, 1-9(2004).
    [41]Kyriaki L. Georgiadou, Eforia G. Tsatsaroni, “Hetarylazo Disperse Dyes Derived from Substituted N,N-bis-β-hydroxy- and N,N-bis-β- acetoxy-ethylaniline”, Dyes and Pigments, 53, 73-78(2002).
    [42]Hitoshi Kusama, Hironori Arakawa, “Influence of Aminothiazole Additives in Redox Electrolyte Solution on Ru(II)-dye-sensi- tized Nanocrystalline TiO2 Solar Cell Performance”, Solar Energy Materials & Solar Cells, 82, 457-465(2004).
    [43]Alan R. Katritzky, Xiaohong Cai, Boris V. Rogovoy, “Solid Phase Synthesis and Application of Trisubstituted Thioureas”, J. Comb. Chem., 5, 392-399(2003).
    [44]Bo Tang, Guo-Ying Zhang, Yang Liu, Fang Han, “Studies on Cata- lytic Spectrophotometry Using β-cyclodextrin Polymer-Schiff Base Metal Complex as Mimetic Enzyme”, Analytica Chimica Acta, 459, 83-91(2002).
    [45]Naozumi Nishizono, Kazuaki Oda, Yutaka Kato, Kosei Ohno, Masaru Minami, Minoru Machida, “Synthesis of Fluorescent Deriva- tization Reagents: Reaction of Isatin with 3-Aryl-7-diethylaminocou- marins and Their Fluorescent Properties”, Heterocycles, 63, 1083-1091(2004).
    [46]John Griffiths, Won Jae Lee, “Synthesis, Light Absorption and Fluorescence Properties of New Thiazole Analogues of The Xanthene Dyes”, Dyes and Pigments, 57, 107-114(2003).
    [47]Daniel E. Lynch, Ian McClenaghan, Mark E. Light, Simon J. Coles, “The Hydrogen-Bonding Networks of 2-Amino-4-phenyl-1,3-thia- zole Derivatives”, Crystal Engineering, 5, 123-136(2002).

    QR CODE
    :::