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

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,与不同碳链长度伯胺进行取代反应制备了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/m L(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,L、a、b值分别为79.7、?10.2、?25.9。

Based on the principle of like dissolves like,1,4-diamino-2,3-dicarboxylic anhydride anthraquinone was used as 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 wavelength of the eight products was in the range of 669~672 nm,which was not affected by the alkyl chain length.The oil solubility of dyes was significantly improved compared with that of 1,4-diamino-2,3 dicarboxylic anhydride anthraquinone.Among them,1,4-diamino-2,3-dicarboxylic anhydride anthraquinone was insoluble in tetrahydrofuran,and product Anthra-n-6(n-hexylamine substituted)had the highest solubility in tetrahydrofuran,which reached 9×10?3 g/mL(25℃).1,4-Diamino-2,3-dicarboxylic anhydride anthraquinone was not used as printing dye,while Anthra-n-6 exhibited the best printing effect.The printed density value was 1.17,L,a and b values were 79.7,?10.2,and?25.9,respectively.