형광증백제로서 1,2-Bis(5-methylbenzoxazol-2-yl)ethylene 유도체의 합성

Abstract

Oxazole fluorescent whitening agents are generally nonionic and insoluble in water. For this reason, its usage is restricted to dyeing of hydrophobic synthetic fibers such as polyester and acrylic fiber. This study focused on developing various oxazole fluorescent whitening agents with better fluorescence and wide range of dyeing application by substituting various functional groups. First, 1,2-bis(5-methylbenzoxazol-2-yl)ethylene (2) was synthesized by dehydration reaction with 2-Amino-pcresol (1) and DL-malic acid. Next, the methyl group of compound 2 was substituted by Wohl-Ziegler bromination with NBS(N-bromosuccinimide) to synthesize 1,2-bis[5-(bromomethyl)benzoxazol-2-yl]ethylene (3). Finally, substitution of the bromomethyl group of compound 3 with various amine groups produced oxazole fluorescent whitening agents (4a~4f) with wide range of dyeing application. In this study, the chemical structures of all the oxazole fluorescent whitening agents (2, 3, 4a~f) were analyzed by IR, 1H and 13C NMR spectrometer. UV-Vis, Fluorescence spectrometer, and Color Difference Meter were used to measure λmax, fluorescence, and whiteness. From the results, we confirmed that the compounds have potential application as fluorescent whitening agents.; Benzoxazole계 형광증백제는 일반적으로 비이온성이며, 물에 용해되지 않는다. 이로 인해 폴리에스터 또는 아크릴 등의 소수성 합성섬유 염색에만 제한적으로 사용되는 단점이 있었다. 이에 본 연구에서는 다양한 작용기를 치환시켜 형광이 우수하고 넓은 범위의 염색 응용성을 갖는 여러 종류의 benzoxazole계 형광증백제를 개발하고자 하였다. 2-Amino-p-cresol (1)과 DL-malic acid를 탈수반응을 통해 1,2-bis(5-methylbenzoxazol-2-yl)ethylene (2)을 합성하고, 화합물 2의 methyl group을 NBS(N-bromosuccinimide)와의 Wohl-Ziegler bromination을 통해 치환하여 1,2-bis[5-(bromomethyl)benzoxazol-2-yl]ethylene (3)을 합성할 수 있었다. 이후 화합물 3의 bromomethyl group과 다양한 amine group의 치환반응으로 넓은 범위의 염색 응용성을 가지는 benzoxazole계 형광증백제(4a~4f)를 합성하였다. 본 연구에서 합성한 모든 benzoxazole계 형광증백제(2, 3, 4a~f)는 IR 및 1H NMR, 13C NMR spectrometer를 이용하여 화학적 구조를 분석하였고 UV-Vis 및 Fluorescence spectrometer와 분광측색기를 통해 각각 λmax와 형광도 및 백색도를 측정하여 물성을 확인하였으며, 그 결과 형광증백제의 사용 가능성을 확인하였다.|Oxazole fluorescent whitening agents are generally nonionic and insoluble in water. For this reason, its usage is restricted to dyeing of hydrophobic synthetic fibers such as polyester and acrylic fiber. This study focused on developing various oxazole fluorescent whitening agents with better fluorescence and wide range of dyeing application by substituting various functional groups. First, 1,2-bis(5-methylbenzoxazol-2-yl)ethylene (2) was synthesized by dehydration reaction with 2-Amino-pcresol (1) and DL-malic acid. Next, the methyl group of compound 2 was substituted by Wohl-Ziegler bromination with NBS(N-bromosuccinimide) to synthesize 1,2-bis[5-(bromomethyl)benzoxazol-2-yl]ethylene (3). Finally, substitution of the bromomethyl group of compound 3 with various amine groups produced oxazole fluorescent whitening agents (4a~4f) with wide range of dyeing application. In this study, the chemical structures of all the oxazole fluorescent whitening agents (2, 3, 4a~f) were analyzed by IR, 1H and 13C NMR spectrometer. UV-Vis, Fluorescence spectrometer, and Color Difference Meter were used to measure λmax, fluorescence, and whiteness. From the results, we confirmed that the compounds have potential application as fluorescent whitening agents.