The present invention relates to azo dyes of formula (1), wherein D is a radical of formula (2) or (3), R.sub.1 and R.sub.2 independently denote hydrogen; C.sub.6-C.sub.10aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; C.sub.1-C.sub.12alkyl which may be interrupted one or more times by —O—, —S—, —NR.sub.4—, —CO—, —COO— or —OOC—, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C.sub.6-C.sub.10aryl, or C.sub.6-C.sub.10aryloxy, which C.sub.6-C.sub.10aryl or C.sub.6-C.sub.10aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C—C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4alkanoylamino; and R.sub.5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4alkanoylamino; and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C.sub.1-C.sub.4alkanoylamino, and the radicals X independently denote N or C—H, with the proviso that at least one radical X denotes C—H, which are distinguished by their good lightfastness properties.

##STR00001##

A printing ink composition includes a disperse dye, a surfactant, a water soluble dye, and a dispersant, in which an IOB value A of the disperse dye, an IOB value B of the surfactant, and an IOB value C of the water soluble dye satisfy the following Equation (1), A<B<C (1), and the IOB value B is 1.0 to 2.0.

Sensors for detecting and distinguishing metals in a sample comprise phenol group-containing azo dyes, the phenol group having one hydroxy involved in reversible metal ion binding and a second hydroxy alkylated to an optically transparent substrate. The sensors have utility for detecting chromium, calcium, magnesium, copper, mercury, nickel, zinc, cobalt, manganese, cadmium, lead, tin, aluminum, potassium, sodium, or arsenic ions in a sample.

Disclosed is an azo compound represented by Formula (I)

##STR00001##

in which R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or methyl, and R.sup.3 is hydrogen, an unsubstituted linear alkyl group of from 1 to 4 carbon atoms, or an unsubstituted branched alkyl group of from 1 to 9 carbon atoms. This disclosure also provides a black dye composition including the azo compound represented by Formula (I).

Disclosed is an azo compound represented by Formula (I), ##STR00001##
in which R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or methyl, and R.sup.3 is hydrogen, an unsubstituted linear alkyl group of from 1 to 4 carbon atoms, or an unsubstituted branched alkyl group of from 1 to 4 carbon atoms. This disclosure also provides a black dye composition including the azo compound represented by Formula (I).

A heat sensitive transfer sheet that achieves high optical density and high light resistance without generating scumming. The heat sensitive sheet has a base material and a coloring material layer formed on the base material, and the coloring material layer includes a compound represented by the following formula (1) and a particular dye compound:

##STR00001##

wherein
R.sup.11 and R.sup.13 each independently represent a hydrogen atom, an alkyl group, an aralkyl group, an unsubstituted aryl group or an aryl group having a substituent; and
R.sup.12 and R.sup.14 to R.sup.18 each independently represent a hydrogen atom or an alkyl group.

Provided herein are dyes for detecting and distinguishing metals in a sample, as well as compositions and methods comprising the same.

##STR00001## ##STR00002## ##STR00003##

The present invention relates to azo dyes of formula (1), wherein D is a radical of formula (2) or (3), R.sub.1 and R.sub.2 independently denote hydrogen; C.sub.6-C.sub.10 aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; C.sub.1-C.sub.12alkyl which may be interrupted one or more times by O, S, NR.sub.4, CO, COO or OOC, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C.sub.6-C.sub.10 aryl, or C.sub.6-C.sub.10 aryloxy, which C.sub.6-C.sub.10 aryl or C.sub.6-C.sub.10 aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino; and R.sub.5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino; and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C.sub.1-C.sub.4 alkanoylamino, and the radicals X independently denote N or CH, with the proviso that at least one radical X denotes CH, which are distinguished by their good lightfastness properties. ##STR00001##

The present invention relates to azo dyes of formula ##STR00001##
wherein R.sub.1 denotes C.sub.1-C.sub.12 alkyl which is unsubstituted or substituted by one or more C.sub.1-C.sub.12 alkoxy groups, hydroxyl groups, amino groups, cyano groups or halogen atoms and which may be interrupted one or more times by the radical O, S, NR.sub.4, COO or OOC; R.sub.4 is hydrogen or C.sub.1-C.sub.12 alkyl; either R.sub.2 is cyano and R.sub.3 is halogen or R.sub.2 is halogen and R.sub.3 is cyano; and Ar represents a carbocyclic or heterocyclic aromatic radical, to the process for the preparation thereof, to mixtures containing said dyes and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic fiber materials, more especially textile materials.

Disclosed are hair color compositions comprising novel stable violet-blue to blue imidazolium azo compounds that have a simplified chromophore and high relative solubility in aqueous systems, and that are surprisingly stable under the conditions of use and storage. These compositions are useful for dyeing fibers such as hair and other keratinaceous materials. The compositions can optionally include an oxidant.