Patent DE-102007018380-A1 (DE)
Title: New cationic aza-benzene compounds useful for the preparation of the agent for dyeing and brightening keratin fibers, preferably human hairs, wool, fur and feathers
Inventor: GROS WIBKE
IPC: A61Q5/10
Filed: 2007-04-17
Abstract: Cationic aza-benzene compounds (I) are new, where (I) are preferably e.g. 5-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,4-dimethyl-4H-1,2,4-triazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-methyl-1,3-thiazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-methyl-1,3-oxazalium salt and 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,3-dimethyl-3H-1,3-imidazalium salt. Cationic aza-benzene compounds of formula (I), are new, where (I) are preferably 5-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,4-dimethyl-4H-1,2,4-triazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-methyl-1,3-thiazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-methyl-1,3-oxazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,3-dimethyl-3H-1,3-imidazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-methyl-1,3,4-thiadiazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3H-1,3-dimethylbenzimidazalium salt, 5-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,4-diallyl-4H-1,2,4-triazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-allyl-1, 3-thiazalium salt, 2-{[4-(1,4,7,10-Tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-allyl-1,3-oxazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,3-diallyl-3H-1,3-imidazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-allyl-1,3,4-thiadiazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3H-1,3-diallylbenzimidazalium salt, 5-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,4-diethyl-4H-1,2,4-triazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-ethyl-1,3-thiazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-3-ethyl-1,3-oxazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl)phenyl]diazenyl}-1,3-diethyl-3H-1,3-imidazalium salt, 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadecan-13-yl) phenyl]diazenyl}-3-ethyl-1,3,4-thiadiazalium salt and 2-{[4-(1,4,7,10-tetroxa-13-azacyclopentadeoan-13-yl)phenyl]diazenyl}-3H-1,3-diethylbenzimidazalium salt, Het+>thiazal-3-ium-2-yl group of formula (a), 2H-pyrazal-1-ium-3-yl of group (b), isothiazal-2-ium-5yl group of formula (c), isoxazal-2-ium-5-yl group of formula (d), 3H-imidazal-1-ium-2yl group of formula (e), [1,3,4]thiadiazal-3-ium-2yl group of formula (f), 4H-[1,2,4]triazal-1-ium-5yl group of formula (g), oxazal-3-ium-2yl group of formula (h), pyridinium-4-yl group of formula (i), pyridinium-2-yl group of formula (j), pyrazalo[1,5-a]pyrimidin-4-ium-5-yl group of formula (k) or pyrazalo[1,5-a]pyrimidin-4-ium-7-yl group of formula (l); either R1>, R2>, R4>, R5>H, 1-6C-alkyl, 2-6C-alkenyl, 1-6C-hydroxyalkyl, 2-6C-polyhydroxyalkyl, 1-5C-alkoxy, hydroxy-1-8C-alkoxy, 1-2C-alkoxy-2-6C-alkyloxy, hydroxy, NO2, amino, 1-6C-alkylamino, di-1-6C-alkylamino, halo, carboxyl, nitrile, carbamoyl, formyl, sulfoneamido, carboxamido, alkyloxycarbonyl or sulfonic acid; or R1>R2>an optionally saturated, optionally substituted carbocyclic or heterocyclic 5-6-membered ring; or R3>, R6>1-6C-alkyl, 2-6C-alkenyl, aryl or arylalkyl (all optionally substituted by OH, carboxyl, sulfonic acid, amino, 1-6C-alkylamino, di-1-6C-alkylamino or 1-6C-alkoxy); K1 : cyclic polyether group, which combines with the nitrogen atom bounded at the aromatic phenyl ring of (I) to form a monoaza substituted crown ether comprising a ring size of 10-25 atoms and 2-6 oxygen atoms, preferably 1,4,7-trioxa-10-aza-cyclododecane-10-yl, 1,4,7-trioxa-10-aza-cyclotridecane-10-yl, 1,4,10-trioxa-7-aza-cyclotridecane-7-yl, 1,4,8-trioxa-11-aza-cyclotetradecane-11-yl, 1,4,7,10-tetraoxa-13-aza-cyclopentadecane-13-yl, 1,4,7,10-tetraoxa-13-aza-cyclohexadecane-13-yl, 1,4,7,13-tetraoxa-10-aza-cyclohexadecane-10-yl, 1,4,10,13-tetraoxa-7-aza-cyclohexadecane-7-yl, 1,5-dioxa-9-aza-cyclododecane-9-yl, 1,7-dioxa-4-aza-cyclododecane-4-yl, 1,7,11-trioxa-4-aza-cyclotetradecane-4-yl or 1,4,7,10,13-pentaoxa-16-aza-cyclooctadecane-16-yl; and X->a univalent anion, preferably halo (Cl, Br, I or F), hydrogen sulfate, semi-sulfate, semi-tetrachlorozincate, p-benzenesulfonate, p-toluenesulfonate, acetate, tetrafluoroborate, trifluoromethanesulfonate, hexafluorophosphate, methane sulfate or methane sulfonate. Independent claims are included for: (1) an agent for dyeing and/or brightening keratin fibers, preferably human hair comprising (I); and (2) a process for dyeing and/or brightening of keratin fibers, preferably human hairs comprising applying a pretreating agent (M1) on the fiber, applying an agent (M2) on the fiber, before the using a further agent (M3), washing the agent (M2) on the fiber after 5-30 minutes, applying an post-treating agent (M4) on the fiber and washing after an impact time of some minutes, where at least one of the agent (M1), (M2) or (M3) is the agent. [Image].