香豆素螢光染料之合成與應用

The Synthesis and Application of Coumarin Fluorescent Dyes

林奕德(Yi-De Lin)

指導教授 ： 趙豫

國立臺北科技大學/工程學院/有機高分子研究所/碩士(2011年)

摘要

隨著生活品質的提高，人們對於衣著的舒適度日漸重視，故潑水加工的需求量也不斷地增加。因此使得外出活動的衣著，均須可考濾潑水功能的設計，所以潑水加工已逐漸成為高附價值紡織的重要工程，但是織物經過了潑水加工處理後，不但手感變差，染色牢度也會降低，加上殘留的潑水劑隨著廢水流出，更造成環境生態污染，因此需要新製程與新藥劑之研發，以改善缺點。目前螢光染料應用在紡織染色、薄膜包覆以及塑膠的研究仍然不斷進行，為增加螢光強度、光安定性和熱安定性等性能。
在本研究中，主要目的在合成一系列潑水性染料以3-羰基、3-(苯並噻唑)、3-(苯並咪唑)香豆素螢光染料，並深入探討聚酯織物之染色性與潑水性以及各項物理性質。自製之染料係由1,3-丙酮二羧酸二甲酯、乙腈苯並噻唑、乙腈苯並咪唑，分別與2,4-二羥基苯甲醛、4-N,N-二乙基胺水楊醛、4-N,N-二丁基胺水楊醛、4-N,N-二己基胺水楊醛、4-N,N-二辛基胺水楊醛和4-N,N-二癸基胺水楊醛等苯甲醛中間體於哌啶存在下進行縮合反應而獲得。合成染料經再結晶純化後，分別以核磁共振光譜儀和質譜儀鑑定其染料結構，並以紫外光/可見光譜儀進行色彩性質探討及潑水性評估、耐水洗牢度、耐水堅牢度、耐汗液染色堅牢度、耐日光染色堅牢度以及表觀色力度之。結果顯示：7號位置增加碳鏈會增加表觀色力度且其水洗、耐汗、耐水牢度都具有4-5級，碳鏈達十個碳以上則具潑水效果。

關鍵字

潑水 ； 3-羰基香豆素 ； 1,3-丙酮二羧酸二甲酯 ； 乙腈苯並噻唑 ； 乙腈苯並咪唑 ； 聚酯 (PET)

並列摘要

With the improvement of quality of life, people pay attention to functional clothing gradually, therefore constantly the demand of water repellent finishingconstomtly increases. It makes the clothing of going out which needs to consider about water repellent, and it become a high value-added processing project. However, fabric process with water repellent finishing, not only hand feeling but dyeing fastness decline, besides, dyeing wastewater with residual water repellent agents result in environmental pollution, therefore it requiring new manufacture procedure and research and development of agents to improve drawbacks. Fluorescent dyes used textiles dyeing covered and plastic have researched, the main purposes were providing raising fluorescence intensity and looking for other applications, especially light stability and thermal stability.
In this study, Three series of Benzothlazole-2-acetonitrile, 2-Benzimidazoleaceto-
nitrile and 3-ketocoumarin.water repellent fluorescent dyes were synthesized and thorough discussion properties of dyeability and water repellency for polyester fabric.These dyes were obtained by condensation of 2,4-dihydroxybenzaldehyde, 4-N,N-diethylaminosalicylaldehyde, 4-N,N-dibutyl-aminosalicylaldehyde, 4-N,N- Dihexyl-aminosalicylaldehyde, 4-N,N-dioctylaminosalicylaldehyde and 4-N,N- didecylaminosalicylaldehyde derivatives with dimethyl 1,3-acetonedicarboxylate in absolute ethanol in the presence of piperidine.
Purification of these dyes was carried out by recrystallization with solvent. The resulting chemical structures of these dyes were subjected to 1H-NMR, mass and UV/Vis analysis for color characteristics. The dyed polyester fabric evaluated by
Water repellency: Spray test assessment, Color fastness to water, Color fastness to washing, Color fastness to perspiration and Color fastness to light of ISO and AATCC and Apparent color strength.
The results showing that color specification value increasing with the increase in the amount of carbon for chain extension of the seventh location of base structure. Simultaneously, the classes of color fastness to water, washing and perspiration are 4-5 or more, the location of structure with the amount of carbon above 10 that achieve water repellency.

並列關鍵字

water repellent ； l,3-ketocoumarin ； dimethyl-1,3-acetonedicarboxylate ； Benzothlazole-2-acetonitrile ； 2-Benzimidazoleacetonitrile ； Polyester (PET)

參考文獻

[5] 李賢斌, "香豆素衍生物之合成以及發光性質之探討, " 碩士倫文, 國立台北科技大學,有機高分子研究所,(2007),pp,8-14.

[8] Murray.R.D.H. "The Natural Coumarins,Occurrence,Chemistry and Biochemistry ", John Wiley and Sons, 1952

[14] Geigy, US Patent 3,014,041 (Dec. 19, 1961)

[15] Geigy, British Patent 914,347 (Jan. 2, 1963)

[16] Geigy, British Patent 1,085,456 (Oct. 4, 1967)