Azo dyes, process for making the same, ink-jet printing ink, ink-jet recording method

An ink-jet printing ink containing an azo dye represented by general formula (1), (10) or (11) as follows:

• wherein, in the general formula (1) and (11), X and X11 represent an electron-withdrawing group having a Hammett's constant σp of at least 0.20;
• R1, R2, R11 and R12 each independently represents a substituted or unsubstituted one of an alkyl group, an alkenyl group, a cycloalkyl group, and an aralkyl group;
• R3, R4, R5, R6, R13, R14, R15, R16 and Y11 each independently represents one of a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclicoxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclicthio group, a sulfinyl group, a phosphoryl group, an acyl group, and an ionic hydrophilic group, each of which groups may have at least one of substituent;
• and each of pair of R1 and R2, R3 and R1, R5 and R2, R11 and R12, R13 and R11, and R15 and R12 may be joined to form a ring;
• Y represents one of a secondary or tertiary alkyl group and a substituted or unsubstituted aryl group;
• A represents a group made up of nonmetallic atoms necessary for forming a 5- to 8-membered ring, which ring may have a substituent, may be a saturated ring, and may have an unsaturated bond;
• Z11 and Z12 each independently represents a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclicoxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclicthio group, a sulfinyl group, a phosphoryl group, an acyl group, or an ionic hydrophilic group;
• and at least one of R11, R12, R13, R14, R15, R16, X11, Y11, Z11, Z12, Z13, Z14, and Z15 represents an ionic hydrophilic group or has an ionic hydrophilic group as a substituent;
• and in the general formula (10), X11 represents an electron-withdrawing group having a Hammett's constant σp of at least 0.20;
• R11, R12, R13, R14, R15, R16 and Y11 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclicoxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclicthio group, a sulfinyl group, a phosphoryl group, an acyl group, or an ionic hydrophilic group;
• each of pairs R11 and R12, R13 and R11, and R12 and R15 may be joined to form a ring;
• A11 represents a group made up of nonmetallic atoms necessary for forming a 5- to 8-membered ring, which may be a saturated ring and may have an unsaturated bond;
• at least 3 of the nonmetallic atoms in the group represented by A11 are substituted with an N atom of a pyrazole ring, Z11, and Z12, respectively, such that the atom substituted with the N atom of the pyrazole ring is adjacent to both the atom substituted with Z11 and the atom substituted with Z12;
• Z11 and Z12 each independently represents a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclicoxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclicthio group, a sulfinyl group, a phosphoryl group, an acyl group, or an ionic hydrophilic group;
• and at least one of R11, R12, R13, R14, R15, R16, X11, Y11, Z11, Z12, and A11 represents an ionic hydrophilic group or has an ionic hydrophilic group as a substituent.