Coloring composition and ink for inkjet recording
There is provided a coloring composition and an ink for inkjet recording which have an excellent ozone fastness and a high print density and is excellent in storage stability over time, and one example of the coloring composition is a coloring composition contains a compound (1A) and a compound (2B):
1. A coloring composition comprising:
a phthalocyanine dye represented by the following Formula (1); and
a phthalocyanine dye represented by the following Formula (I-2), the following Formula (II-2), or the following Formula (III-2):
wherein, in formula (1),
R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 each independently represent 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 amide 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, 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 imide group, a heterocyclic thio group, a phosphoryl group, an acyl group, or an ionic hydrophilic group, and these groups may further have a substituent,
Z 1 , Z 2 , Z 3 and Z 4 each independently represent 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, provided that at least one of Z 1 , Z 2 , Z 3 and Z 4 has an ionic hydrophilic group as a substituent,
l, m, n, p, q 1 , q 2 , q 3 and q 4 each independently represent 1 or 2, and
M 1 represents a hydrogen atom, a metal element, a metal oxide, a metal hydroxide or a metal halide:
Formula (I-2):
wherein, in Formula (I-2),
R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 each independently represent 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 amide 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, 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 imide group, a heterocyclic thio group, a phosphoryl group, an acyl group, or an ionic hydrophilic group, and these groups may further have a substituent,
Z 5 , Z 6 , Z 7 , and Z 8 each independently represent 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, provided that at least one of Z 5 , Z 6 , Z 7 and Z 8 has an ionic hydrophilic group as a substituent,
t, u, v, w, q 5 , q 6 , q 7 and q 8 each independently represent 1 or 2, and
M 2 represents a hydrogen atom, a metal element, a metal oxide, a metal hydroxide or a metal halide:
Formula (II-2):
wherein, in Formula (II-2),
P's each independently represents a nitrogen atom or CH, and at least one of P's represents a nitrogen atom, provided that in four rings containing P's, each of the number of P's representing nitrogen atoms is 2 or less,
R 21 and R 22 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group,
R 23 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group,
R 24 represents a substituted or unsubstituted hydrocarbon group,
R 23 and R 24 may be bound to each other with a nitrogen atom to form a substituted or unsubstituted heterocyclic ring, and
x, y, and z each independently represent 0 to 4, provided that x+y+z is 1 to 4:
Formula (III-2):
wherein, in Formula (III-2),
R 17 and R 18 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted alkenyl group,
A represents a divalent linking group,
R 17 and R 18 adjacent to A, and A may be bound to each other to form a ring,
Y and Z each independently represents a halogen atom, a hydroxyl group, a sulfonate group, a carboxyl group, an amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic oxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted alkenyloxy group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted cycloalkyl amino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted heterocyclic amino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted alkenyl amino group, a substituted or unsubstituted dialkylamino group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted aralkyl thio group, or a substituted or unsubstituted alkenylthio group, provided that at least one of Y and Z has a sulfonate group, a carboxyl group, or an ionic hydrophilic group as a substituent, and
m and n is 1 to 3, and the sum of m and n is 2 to 4.
2. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (I-2), Z 5 , Z 6 , Z 7 , and Z 8 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
3. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (I-2), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 are a hydrogen atom.
4. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (I-2), Z 5 , Z 6 , Z 7 , and Z 8 represent a substituted alkyl group, and at least one substituent which the substituted alkyl group has is —SONHR group where R represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group.
5. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (I-2), t, u, v and w are 1.
6. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (I-2), q 5 , q 6 , q 7 and q 8 are 2.
7. The coloring composition according to claim 1 ,
wherein an azaphthalocyanine dye represented by Formula (II-2) is an azaphthalocyanine dye represented by Formula (II-3-1) or Formula (II-3-2):
wherein, in Formula (II-3-1) and Formula (II-3-2),
P's each independently represents a nitrogen atom or CH, and at least one of P's represents a nitrogen atom,
R 21 and R 22 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group,
R 23 and R 24 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and
x, y, and z each independently represent 0 to 4, provided that x+y+z is 1 to 4.
8. The coloring composition according to claim 1 ,
wherein in Formula (II-2), Formula (II-3-1), or Formula (II-3-2), R 23 represents a hydrogen atom and R 24 is a substituted alkyl group substituted with a substituent represented by Formula (T1):
wherein, in Formula (T1),
L represents a single bond or a substituted or unsubstituted alkylene group,
X's each independently represents a substituent selected from —OR 25 , —SR 25 , and —NR 25 R 26 , and R 25 and R 26 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and at least one of R 25 and R 26 has an ionic hydrophilic group as a substituent, and
R 27 represents a hydrogen atom or a substituted or unsubstituted alkyl group.
9. The coloring composition according to claim 8 ,
wherein the substituent represented by Formula (T1) is a substituent represented by Formula (T2):
wherein, in Formula (T2),
L represents a single bond or a substituted or unsubstituted alkylene group,
R 29 , R 210 , and R 211 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group,
R 212 represents a substituted alkyl group, a substituted aryl group, or a substituted heterocyclic group, and has at least one ionic hydrophilic group as a substituent, and
R 27 represents a hydrogen atom or a substituted or unsubstituted alkyl group.
10. The coloring composition according to claim 1 ,
wherein the phthalocyanine dye represented by the Formula (III-2) is a phthalocyanine dye represented by the Formula (III-2-1):
wherein, in Formula (III-2-1),
R 27 and R 28 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted alkenyl group,
A represents a divalent linking group,
R 27 and R 28 adjacent to A, and A may be bound to each other to form a ring,
R 29 , R 210 , and R 211 each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group,
R 212 represents a sulfonate group, a carboxyl group, a substituted alkyl group, a substituted aryl group, or a substituted heterocyclic group, and has at least one ionic hydrophilic group as a substituent, and
m and n are 1 to 3, and the sum of m and n is 2 to 4.
11. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (1), R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are a hydrogen atom.
12. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (1), Z 1 , Z 2 , Z 3 , and Z 4 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
13. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (1), l, m, n and p are 1.
14. The coloring composition according to claim 1 ,
wherein in the phthalocyanine dye represented by Formula (1), q 1 , q 2 , q 3 and q 4 are 2.
15. The coloring composition according to claim 1 , further comprising a compound represented by Formula (AB9):
wherein, in Formula (AB9),
Me represents a methyl group, and
M represents a hydrogen atom, a lithium, a sodium, a potassium, or an ammonium.
16. The coloring composition according to claim 1 ,
wherein a mass ratio of the phthalocyanine dye represented by Formula (1) to the phthalocyanine dye represented by Formula (I-2), Formula (II-2), or Formula (III-2) is 50/50 to 10/90.
17. The coloring composition according to claim 1 ,
wherein a content of the phthalocyanine dye represented by Formula (1) is 1% by mass to 20% by mass.
18. The coloring composition according to claim 15 ,
wherein a mass ratio of the total amount of the phthalocyanine dye represented by Formula (1) and the phthalocyanine dye represented by Formula (I-2), Formula (II-2), or Formula (III-2) to the compound represented by Formula (AB9) is 90/10 to 99/1.
19. An ink for inkjet recording comprising the coloring composition according to claim 1 .