Azo dye, ink jet recording ink, heat sensitive recording material, color toner, color filter, ink jet recording method, ink cartridge and ink jet printer
An azo dye represented by formula (II) as defined in the specification, a process of producing the same and a coloring composition containing the azo dye.
1. An azo dye represented by formula (I):
wherein A represents a residue of a 5-membered heterocyclic diazo component A-NH 2 ;
B 1 and B 2 each represents ═CR 1 — or ═CR 2 —, or one of B 1 and B 2 represents a nitrogen atom and the other of B 1 and B 2 represents ═CR 1 — or ═CR 2 —;
R 3 and R 4 each independently represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group or a sulfamoyl group, each of the groups optionally has a substituent;
R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a carboxyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a hydroxyl group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, a heterocyclic oxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an alkylamino group, an arylamino group, a heterocyclic amino group, an acylamino group, an ureido group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an alkylsulfonylamino group, an aryloxycarbonylamino group, a nitro group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a sulfo group or a heterocyclic thio group, each of the groups optionally has a substituent, and R 1 and R 3 are optionally taken together, or R 3 and R 4 are optionally taken together, each to form a 5- or 6-membered ring;
a and e each independently represents an alkyl group, and the alkyl groups represented by a and e have at least three carbon atoms in total that constitute the alkyl groups, and each of the groups optionally has a substituent;
b, c, and d each independently has a same meaning as R 1 and R 2 , and a and b are optionally taken together, or e and d are optionally taken together, each to form a condensed ring; and
formula (I) has at least one ionic hydrophilic group.
2. The azo dye according to claim 1 , which is represented by formula (II):
wherein each of R 1 , R 2 , R 3 , R 4 , a, b, c, d, and e is the same as defined in formula (I);
Z 1 represents an electron attracting group having a Hammett substituent constant ap of 0.20 or more;
Z 2 represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group;
Q represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, and each of the groups represented by Z 1 , Z 2 , and Q optionally has a substituent; and
formula (II) has at least one ionic hydrophilic group.
3. A process of producing a compound represented by formula (II) according to claim 2 , the process comprising:
(a) allowing an aminopyrazole represented by formula (III) to react with a diazotizing agent to form a diazonium salt;
(b) allowing the diazonium salt to react with a coupling agent represented by formula (IV) to form a compound represented by formula (II-H1); and
(c) allowing the compound represented by formula (II-H1) to react with an alkylating agent, an arylating agent or a heterylating agent in a presence of a base to form a compound represented by formula (II-R1):
wherein each of Z 1 , Z 2 , R 1 , R 2 , R 3 , R 4 , a, b, c, d, and e is the same as defined in formula (II); and
Q 1 represents an aliphatic group, an aromatic group or a heterocyclic group.
4. The process of producing a compound represented by formula (II) according to claim 3 , wherein the compound represented by formula (II-R1) is a compound represented by formula (II-R2):
wherein each of Z 1 , Z 2 , R 1 , R 2 , R 3 , R 4 , a, b, c, d, and e is the same as defined in formula (II); and
Q 1 and Q 2 , which are the same or different, each independently represents an aliphatic group, an aromatic group or a heterocyclic group.
5. A process of producing a compound represented by formula (II) according to claim 2 , the process comprising:
introducing a water soluble group into a compound represented by formula (II-R1) or formula (II-R2) by an electrophilic reaction,
wherein each of Z 1 , Z 2 , R 1 , R 2 , R 3 , R 4 , a, b, c, d, and e is the same as defined in formula (II); and
Q 1 and Q 2 , which are the same or different, each independently represents an aliphatic group, an aromatic group or a heterocyclic group.
6. The azo dye according to claim 1 ,
wherein the at least one ionic hydrophilic group contains a sulfo group.
7. The azo dye according to claim 6 ,
wherein the sulfo group has a counter ion, and
wherein the counter ion is a lithium ion.
8. An ink jet recording ink comprising at least one azo dye according to claim 1 .
9. An ink jet recording method, which comprises forming an image with an ink jet recording ink according to claim 8 on an image receiving material comprising a substrate and an ink receiving layer containing an inorganic white pigment.
10. An ink cartridge comprising an ink jet recording ink according to claim 8 .
11. An ink jet printer comprising an ink cartridge according to claim 10 .
12. A heat sensitive recording material comprising at least one azo dye according to claim 1 .
13. A color toner comprising at least one azo dye according to claim 1 .
14. A color filter comprising at least one azo dye according to claim 1 .
15. The azo dye according to claim 1 , wherein formula (I) comprises 3 to 6 ionic hydrophilic groups.
16. The azo dye according to claim 1 , wherein the ionic hydrophilic group is selected from the group consisting of a carboxyl group, a phosphono group, and a sulfo group.
17. The azo dye according to claim 16 , wherein the ionic hydrophilic group is a sulfo group.
18. The azo dye according to claim 1 , wherein a and e are each a substituted or unsubstituted alkyl group.
19. The azo dye according to claim 1 , wherein a + e have 3 to 5 carbon atoms in total.
20. The azo dye according to claim 1 , wherein the azo dye is represented by formula (I-1):
wherein each of A, B 1 , B 2 , R 3 , a, b, c, d and e is the same as defined in formula (I), wherein each a can be the same or different, each b can be the same or different, each c can be the same or different, each d can be the same or different, and each e can be the same or different.
21. The azo dye according to claim 1 , wherein the azo dye is represented by formula (I-2):
wherein a, c and e each independently represents a hydrogen atom or an unsubstituted alkyl group; W 1 , W 2 and W 3 each independently represents a hydrogen atom or a sulfo group, provided that the sum total of the carbon number of a and e per ring is 3 to 6, and all of W 1 , W 2 and W 3 are not hydrogens at the same time.