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##

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##

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 (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 invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E.sub.1 and E.sub.2 are independently from each other CH or N, An is an anion and a is a number from 1 to 6 and R.sub.1 and R.sub.2 are independently from each other and further specified. The compounds show washfastness at hair-dying. ##STR00001##

The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E.sub.1 and E.sub.2 are independently from each other CH or N, An is an anion and a is a number from 1 to 6 and R.sub.1 and R.sub.2 are independently from each other and further specified. The compounds show washfastness at hair-dying. ##STR00001##

The present invention provides a family of dark quenchers, termed Black Hole Quenchers (BHQs), that are efficient quenchers of excited state energy but which are themselves substantially non-fluorescent. Also provided are methods of using the BHQs, probes incorporating the BHQs and methods of using the probes.

The present invention provides a family of dark quenchers, termed Black Hole Quenchers (BHQs), that are efficient quenchers of excited state energy but which are themselves substantially non-fluorescent. Also provided are methods of using the BHQs, probes incorporating the BHQs and methods of using the probes.

Azo anthrapyridone dye of general formula (III) wherein A, R.sub.1, R.sub.2, B, M and n are as described in the specification, are excellent magenta dyes for dyeing and printing of paper, other cellulose containing materials and textiles materials and, in particular, for the preparation of recording fluids for ink jet printing and for writing utensils.

##STR00001##

Azo anthrapyridone dye of general formula (III) wherein A, R.sub.1, R.sub.2, B, M and n are as described in the specification, are excellent magenta dyes for dyeing and printing of paper, other cellulose containing materials and textiles materials and, in particular, for the preparation of recording fluids for ink jet printing and for writing utensils.

##STR00001##