N-烷基邻苯二甲酰亚胺分散染料合成与光谱性能(待续)
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摘要
以硝基取代邻苯二甲酰亚胺为原料,通过N-烷基化、硝基还原、溴基取代、氰基取代、重氮化偶合等反应制备了一系列染料中间体及乙基、丁基及其溴基和氰基取代等包括黄色、红色和蓝色色光的6只邻苯二甲酰亚胺分散染料,利用红外光谱、核磁共振谱、质谱和元素分析等对中间体和染料进行了表征。结果表明:乙基和丁基取代对染料最大吸收波长(λmax)的影响较小,邻苯二甲酰亚胺基团在苯环上取代溴基或氰基后对染料分别产生浅色效应和深色效应。溴原子的空间阻碍作用造成共轭体系破坏产生蓝移,氰基较强的吸电子效应使染料产生红移。相比三氯甲烷和甲苯,染料在介电常数较大的丙酮、DMF、乙醇溶剂中产生红移。
A series of intermediates and six N-alkyl(ethyl, butyl) substituted, dibromo-substituted and dicyano-substituted phthalimide azo disperse dyes, including yellow, red and blue color shade, were synthesized by nitro substituted phthalimide through alkylation, amination, bromination, diazotization coupling reaction. All of the synthesized intermediates and dyes had been characterized by FTIR, 1 H-NMR, MS and elemental analysis. The results showed that ethyl and butyl substitution had little influence on the UV-Vis maximum absorption wavelength(λmax) of dyes. Bromo and cyano substitution on the phthalimide ring resulted in hypsochromic and bathochromic effect on dyes, respectively. The space hindrance of bromine atoms destroyed the conjugated system and caused hypsochromicshift. The strong electron-withdrawing cycano substitution caused bathochromic shift. Compared with trichloro-methane and toluene, dyes in acetone, DMF and ethanol solvents with larger dielectric constant caused bathochromic shift.
A series of intermediates and six N-alkyl(ethyl, butyl) substituted, dibromo-substituted and dicyano-substituted phthalimide azo disperse dyes, including yellow, red and blue color shade, were synthesized by nitro substituted phthalimide through alkylation, amination, bromination, diazotization coupling reaction. All of the synthesized intermediates and dyes had been characterized by FTIR, 1 H-NMR, MS and elemental analysis. The results showed that ethyl and butyl substitution had little influence on the UV-Vis maximum absorption wavelength(λmax) of dyes. Bromo and cyano substitution on the phthalimide ring resulted in hypsochromic and bathochromic effect on dyes, respectively. The space hindrance of bromine atoms destroyed the conjugated system and caused hypsochromicshift. The strong electron-withdrawing cycano substitution caused bathochromic shift. Compared with trichloro-methane and toluene, dyes in acetone, DMF and ethanol solvents with larger dielectric constant caused bathochromic shift.
引文