1,4-二氨基-2,3邻苯二甲酰亚胺蒽醌染料的合成与应用

Synthesis and Application of 1,4-Diamino-2,3- Phthalimide-Anthraquinone Dyes

摘要:

基于相似相溶原理，以1,4-二氨基-2,3-二羧酸酐蒽醌为原料，通过与不同碳链长度伯胺的取代反应制备了8种油溶性1,4-二氨基-2,3-邻苯二甲酰亚胺蒽醌类蓝色染料。对合成的8种染料在常见有机溶剂中的溶解度和紫外吸收性能进行了测试，结果表明，8种产物的最大吸收波长均在669～672 nm，不受产物中烷基链长度的影响。染料的油溶性相对于1,4-二氨基-2,3二羧酸酐蒽醌得到明显提升。其中1,4-二氨基-2,3-二羧酸酐蒽醌在四氢呋喃等有机溶剂中不溶，产物Anthra-n-6(正己胺取代)在四氢呋喃中的溶解度最大，可达到9×10-3 g/mL(25 ℃)。1,4-二氨基-2,3-二羧酸酐蒽醌无法作为打印染料而Anthra-n-6打印效果最好，打印的色密度值为1.17，Lab值分别为79.7、-10.2、-25.9。

Abstract:

Based on the principle of like dissolves like principle, 1,4-diamino-2,3-dicarboxylic anhydride anthraquinone was used as a raw material to prepare eight oil-soluble 1,4-diamino-2,3-phthalimide anthraquinone dyes by substitution reaction with primary amines of different carbon chain lengths. The solubility and UV absorption properties of the synthesized 8 dyes in common organic solvents were tested. The results show that the maximum absorption wavelengths of the eight products are all in the range of 669～672 nm, which is not affected by the length of the alkyl chain in the product. The oil solubility of dyes is significantly improved relative to 1,4-diamino-2,3 dicarboxylic anhydride anthraquinone. Among them, 1,4-diamino-2,3-dicarboxylic anhydride anthraquinone is insoluble in an organic solvent such as tetrahydrofuran, and the product Anthra-n-6 (n-hexylamine substituted) has the highest solubility in tetrahydrofuran which can reach 9×10-3 g/mL (25 ℃). 1,4-Diamino-2,3-dicarboxylic anhydride anthraquinone can not be used as a printing dye and Anthra-n-6 has the best printing effect. The printed density value was 1.17, and the Lab values were 79.7, -10.-2, -25.9, respectively.