Phthalocyanine compound, ink, inkjet recording ink, ink-jet recording method and method for improving ozone gas resistance of color image material

An ink comprising a phthalocyanine compound having an oxidation potential nobler than 1.0 V (vs SCE), wherein the ink comprises at least one compound represented by the following formula (I) or (II):

• wherein X1, X2, X3 and X4 each independently represents —SO-Z or —SO2-Z, wherein each Z independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
• Y1, Y2, Y3 and Y4 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 sulfonamido group, a carbamoyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group;
• a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a phosphoryl group, an acyl group or an ionic hydrophilic group, which groups each may further have a substituent;
• a1 to a4 and b1 to b4 represent a number of substituents X1 to X4 and Y1 to Y4, respectively, a1 to a4 each independently represents an integer of 0 to 4, provided that all are not 0 at the same time, and b1 to b4 each independently represents an integer of 0 to 4;
• and
• M represents a hydrogen atom, a metal element or an oxide, hydroxide or halide thereof;
• provided that at least one of X1, X2, X3, X4, Y1, Y2, Y3 and Y4 is an ionic hydrophilic group or a group having an ionic hydrophilic group as a substituent:
• wherein X11, X12, X13 and X14 each independently represents —SO2NR1R2 and/or a sulfo group, provided that X11, X12, X13 and X14 all are not a sulfo group at the same time, wherein R1 represents, when a plurality of R1s are present, each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, R2, represents, when a plurality of R2s are present, each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and R1 and R2 may combine with each other to form a 5- or 6-membered nitrogen-containing heterocyclic ring;
• wherein at least one —SO2NR1R2 group having an ionic hydrophilic group is present at the 2-, 3-, 6-, 7-, 10-, 11-, 14- or 15-position of formula (II);
• wherein when a sulfo group is directly bonded to a benzene nucleus, the sulfo group is bonded at the 2-, 3-, 6-, 7-, 10-, 11-, 14- or 15-position of formula (II);
• Y11, Y12, Y13, Y14, Y15, Y16, Y17 and Y18 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 sulfonamido group, a carbamoyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a phosphoryl group, an acyl group or an ionic hydrophilic group, which groups each may further have a substituent;
• a11 to a14 represent a number of substituents X11 to X14, respectively, and each independently represents an integer of 0 to 2, provided that all are not 0 at the same time;
• and
• M represents a hydrogen atom, a metal element or an oxide, hydroxide or halide thereof;
• provided that at least one of X11, X12, X13, X14, Y11, Y12, Y13, Y14, Y15, Y16, Y17 and Y18 is an ionic hydrophilic group or a group having an ionic hydrophilic group as a substituent.

A phthalocyanine compound represented by the formula (I) or (II):

• wherein X1, X2, X3 and X4 each independently represents —SO-Z or —S2-Z, wherein each Z independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group;
• Y1, Y2, Y3 and Y4 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 sulfonamido group, a carbamoyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a phosphoryl group, an acyl group or an ionic hydrophilic group, which groups each may further have a substituent;
• a1 to a4 and b1 to b4 represent a number of substituents X1 to X4 and Y1 to Y4, respectively, a1 to a1 each independently represents an integer of 0 to 4, provided that all are not 0 at the same time, and b1 to b4 each independently represents an integer of 0 to 4;
• and
• M represents a hydrogen atom, a metal element or an oxide, hydroxide or halide thereof;
• provided that at least one of X1, X2, X3, X4, Y1, Y2, Y3 and Y4 is an ionic hydrophilic group or a group having an ionic hydrophilic group as a substituent;
• wherein X11, X12, X13 and X14 each independently represents —SO2NR1R2 and/or a sulfo group, provided that X11, X12, X13 and X14 all are not a sulfo group at the same time, wherein R1 represents, when a plurality of R1 s are present, each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, R2 represents, when a plurality of R2s are present, each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and R1 and R2 may combine with each other to form a 5- or 6-membered nitrogen-containing heterocyclic ring;
• wherein at least one —SO2NR1R2 group having an ionic hydrophilic group is present at the 2-, 3-, 6-, 7-, 10-, 11-, 14- or 15-position of formula (II);
• wherein when a sulfo group is directly bonded to a benzene nucleus, the sulfo group is bonded at the 2-, 3-, 6-, 7-, 10-, 11-, 14- or 15-position of formula (II);
• Y11, Y12, Y13, Y14, Y15, Y16, Y17 and Y18 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 sulfonamido group, a carbamoyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a phosphoryl group, an acyl group or an ionic hydrophilic group, which groups each may further have a substituent;
• a11 to a14 represent a number of substituents X11 to X14, respectively, and each independently represents an integer of 0 to 2, provided that all are not 0 at the same time;
• and
• M represents a hydrogen atom, a metal element or an oxide, hydroxide or halide thereof;
• provided that at least one of X11, X12, X13, X14, Y11, Y12, Y13, Y14, Y15, Y16, Y17 and Y18 is an ionic hydrophilic group or a group having an ionic hydrophilic group as a substituent.