申请人:MINNESOTA MINING AND MANUFACTURING COMPANY
公开号:EP0561686A1
公开(公告)日:1993-09-22
2-Methyl-4,4a-dihydro-3H-carbazolium salts that are useful as dye precursors and dyes derived from those precursors are disclosed. The salts are described by the formula
wherein R¹ represents an alkyl, aryl, sulfoalkyl, carboxyalkyl, sulfatoalkyl, alkoxyalkyl, acyloxyalkyl, dialkylaminoalkylene, cycloaminoalkylene, acyl, or alkenyl group having from 1 to 18 carbon atoms; R² represents an alkyl group having up to 18 carbon atoms; R³represents hydrogen or an alkyl group having from 1 to 18 carbon atoms; R⁴ represents hydrogen or an alkyl group having from 1 to 18 carbon atoms; R⁵ represents hydrogen, nitro, carboxyl, sulfo, hydroxy, halogen, phospho, or an alkoxy, thioalkoxy, oxyalkyl, acyl, alkyl, aryl, or amino group having up to 18 carbon atoms; wherein any two groups R⁵, or R⁴ and a group R⁵, or R¹ and R⁴ may together form a substituted or unsubstituted aryl, heteroaryl, aliphatic, or heteroaliphatic ring; X represents an anion; and a and b represent positive integers such that a equals b.
The salts have a partially saturated ring system that rigidifies the chromophore in the precursor and in dyes derived from it. The rigidified chromophores have narrowed absorption bands relative to corresponding non-rigid chromophores. Dyes prepared from the dye precursors of the invention typically have good solubility in non-polar solvents.
本发明公开了可用作
染料前体的 2-甲基-4,4a-二氢-3H-
咔唑盐以及由这些前体衍生的
染料。这些盐的结构式如下
其中 R¹ 代表具有 1 至 18 个碳原子的烷基、芳基、磺酰基、羧基、
硫代烷基、烷氧基烷基、酰氧基烷基、二烷基
氨基烷基、环
氨基烷基、酰基或烯基;R² 代表具有多达 18 个碳原子的烷基;R³ 代表氢或具有 1 至 18 个碳原子的烷基;R⁴ 代表氢或具有 1 至 18 个碳原子的烷基;R⁵ 代表氢、硝基、羧基、磺基、羟基、卤素、膦基或具有多达 18 个碳原子的烷氧基、
硫代烷氧基、氧代烷基、酰基、烷基、芳基或
氨基;其中任意两个基团 R⁵ 或 R⁴ 和一个基团 R⁵ 或 R¹ 和 R⁴ 可共同形成取代或未取代的芳基、杂芳基、脂族或杂脂族环;X 代表阴离子;a 和 b 代表正整数,使得 a 等于 b。
盐类具有部分饱和的环系统,可硬化前体和衍生
染料中的发色团。与相应的非刚性发色团相比,刚性发色团的吸收带变窄。由本发明
染料前体制备的
染料通常在非极性溶剂中具有良好的溶解性。