Trisazo Compound, Ink Composition, Recording Method, and Colored Article

• US 20090062545A1
• Filed: 12/28/2006
• Published: 03/05/2009
• Est. Priority Date: 01/06/2006
• Status: Active Grant

• Current Assignee: Nippon Kayaku Company Limited
• Original Assignee: Nippon Kayaku Company Limited
• Inventors: Dejima, Yoshiyuki, Yoshimoto, Takashi, Hirota, Koji, Morita, Ryoutarou, Matsui, Takahiko
• Granted Patent: US 8,167,991 B2
• Time in Patent Office: Days
• US Class Current: 546/86
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C09B 31/28 Heterocyclic compounds
• CPC Class Codes: C09D 11/17 characterised by colouring agents
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

The present invention relates to a trisazo compound represented by the following formula (1) or a salt thereof,

The formula (1)

(wherein, the group A is a substituted phenyl group, the group B and the group C are substituted para-phenylene groups, R¹ represents a C1 to C4 alkyl group (which may be substituted by a carboxy group), a phenyl group (which may be substituted by a sulfo group), or a carboxy group,
R² represents a cyano group, a carbamoyl group or a carboxy group, each of R³ and R⁴ independently represents a hydrogen atom, a methyl group, a chlorine atom or a sulfo group, respectively) and a water-based black ink composition containing said compound; said compound has high solubility in a medium where the main component is water, its aqueous solution having a high concentration and ink are stable when stored for a long period of time, black-recorded images with it can be provided where both light fastness and ozone gas fastness of the printed images are excellent.

Claims

1. A trisazo compound represented by the following formula (1) in free acid form

(wherein, the group A is a substituted phenyl group and has a substituent selected from the group consisting of a carboxy group, a sulfo group, a chlorine atom, a cyano group, a nitro group, a sulfamoyl group, a C1 to C4 alkyl group, a C1 to C4 alkoxy group (which may be substituted by a hydroxy group, a C1 to C4 alkoxy group, a sulfo group or a carboxy group) and a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group, a sulfo group or a carboxy group),

B and C are substituted para-phenylene groups and have a substituent selected from the group consisting of a carboxy group, a sulfo group, a C1 to C4 alkyl group and a C1 to C4 alkoxy group (which may be substituted by a hydroxy group, a C1 to C4 alkoxy group, a sulfo group or a carboxy group),

R¹ represents a C1 to C4 alkyl group which may be substituted by a carboxy group, a phenyl group which may be substituted by a sulfo group, or a carboxy group,

R² represents a cyano group, a carbamoyl group or a carboxy group,

each of R³ and R⁴ independently represents a hydrogen atom, a methyl group, a chlorine atom or a sulfo group, respectively) or a salt thereof.

2. The trisazo compound or the salt thereof according to claim 1, wherein the substituent of the group A is a sulfo group or a carboxy group and at least one of the substituents on the group B and the group C is a sulfo group or a sulfopropoxy group.

3. The trisazo compound according to claim 1, wherein the group B and the group C in the formula (1) are groups represented by the following formula (2),

(wherein, R⁵ represents a sulfo group or a sulfopropoxy group, and R⁶ represents a hydrogen atom, a methyl group, an ethyl group, a methoxy group or an ethoxy group, respectively).

4. The trisazo compound according to claim 3, wherein in the formula (1), R¹ is a methyl group, R² is a cyano group or a carbamoyl group, R³ is a hydrogen atom, and R⁴ is a sulfo group.

5. The trisazo compound or the salt thereof according to claim 3, wherein in the formula (1), the substituent of the group A is a sulfo group or a carboxy group, R¹ is a methyl group, R² is a cyano group or a carbamoyl group, R³ is a hydrogen atom, R⁴ is a sulfo group, the group B and the group C are represented by the above formula (2), R⁵ is a sulfo group or a sulfopropoxy group, and R⁶ is a hydrogen atom or a methyl group.

6. The trisazo compound or the salt thereof according to claim 3, wherein, in the formula (1), the substituent of the group A is a sulfo group and its substitution position is the para-position to the azo group, R¹ is a methyl group, R² is a cyano group or a carbamoyl group, R³ is a hydrogen atom, R⁴ is a sulfo group, and the group B and the group C are represented by the above formula (2) where in the group B, R⁵ is a sulfo group and R⁶ is a hydrogen atom, and in the group C, R⁵ is a sulfopropoxy group and R⁶ is a methyl group.

7. An ink composition characterized by containing at least one kind of the trisazo compound according to claim 1.

8. An inkjet print recording method characterized by using the ink composition according to claim 7.

9. The inkjet print recording method according to claim 8, wherein a record-receiving material in the inkjet print recording method is a communication sheet.

10. The inkjet print recording method according to claim 9, wherein the communication sheet is a sheet containing a porous white inorganic substance.

11. An ink jet printer loading a container containing the ink composition according to claim 10.

12. A colored article colored with the trisazo compound according to claim 1 or the ink composition according to claim 7.

13. The trisazo compound according to claim 1, wherein in the formula (1), at least either one of the group B and the group C is a para-phenylene group substituted by a sulfo C1 to C4 alkoxy group (said phenylene group may be further substituted by a C1 to C4 alkyl group).

14. The trisazo compound according to claim 13, wherein in the formula (1), at least either one of the group B and the group C is a 2-sulfo C1 to C4 alkoxy-5-C1 to C4 alkyl-1,4-phenylen group.

15. The trisazo compound according to claim 1 or 13, wherein, in the formula (1), the group A is a phenyl group which has a sulfo group, a sulfo C1 to C4 alkoxy group or a sulfo C1 to C4 alkylsulfonyl group as one substituent and further may be substituted by a sulfo group, a carboxy group, a C1 to C4 alkoxy group or a nitro group, or a dicarboxy-substituted phenyl group.

16. The trisazo compound according to claim 15, wherein in the formula (1), R¹ is a C1 to C4 alkyl group which may be substituted by a carboxy group, or a phenyl group, R² is a cyano group, a carbamoyl group or a carboxy group, and one of R³ and R⁴ is a hydrogen atom and the other is a sulfo group.

17. The trisazo compound according to claim 1 or 13, wherein the formula (1), the group A is a 4-sulfophenyl group, a 2-carboxy-4-sulfophenyl group, a 2,4- or 2,5-disulfophenyl group, a 4-sulfo C1 to C4 alkoxyphenyl group, a 2-sulfo-4-(nitro or C1 to C4 alkoxy)phenyl group or a 3,5-dicarboxyphenyl group.

18. The trisazo compound according to claim 17, wherein in the formula (1), both the group B and the group C are 3-sulfo C1 to C4 alkoxy-6-C1 to C4 alkyl-1,4-phenylene groups, R¹ is a C1 to C4 alkyl group which may be substituted by a carboxy group, R² is a cyano group, and one of R³ and R⁴ is a hydrogen atom and the other is a sulfo group.

19. The trisazo compound according to claim 1, wherein in the formula (1), the group A is a 2,4-disulfophenyl group, both the group B and the group C are 2-(3-sulfopropoxy)-5-methyl-1,4-phenylene groups, R¹ is a methyl group, R² is a cyano group, one of R³ and R⁴ is a hydrogen atom and the other is a sulfo group.

20. The water-based black ink composition according to claim 7, which contains the three of (a) the trisazo compound according to claims 1, (b) a dye having a maximum absorption wavelength in the range of 350 nm to 550 nm and (c) a dye having a maximum absorption wavelength in the range of 560 nm to 660 nm.

21. The water-based black ink composition according to claim 20, wherein (b) a dye having a maximum absorption wavelength in the range of 350 nm to 550 nm is the following formula (5)

(wherein, R³¹ represents a hydrogen atom;

a hydroxy group;

a carboxy group;

a C1 to C4 alkyl group which may be substituted by a hydroxy group or a C1 to C4 alkoxy group;

a C1 to C4 alkoxy group which may be substituted by a hydroxy group or a C1 to C4 alkoxy group;

a C1 to C4 alkylamino group which may be substituted by a hydroxy group or a C1 to C4 alkoxy group;

a carboxy C1 to C5 alkylamino group;

a bis[carboxy C1 to C5 alkyl]amino group; and

a C1 to C4 alkanoylamino group which may be substituted by a hydroxy group or a C1 to C4 alkoxy group;

a phenylamino group which may be substituted by a carboxy group, a sulfonic acid group or an amino group;

a sulfo group;

a halogen atom or a ureide group, and the group A″

represents a substituted alkylamino group (the substituent on said alkyl group is a carboxy group or a sulfo group), respectively).

22. The water-based black ink composition according to claim 20, wherein (c) a dye having a maximum absorption wavelength in the range of 560 nm to 660 nm is a compound represented by the following formula (I-2) or a salt thereof,

Formula (I-2):

(wherein, each of R²¹ and R²² independently represents a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a sulfo group, a sulfamoyl group, an N-alkylaminosulfonyl group, an N-phenylaminosulfonyl group, a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group), a phosphono group, a nitro group, an acyl group, a ureide group, a C1 to C4 alkyl group (which may be substituted by a group selected from the group consisting of a hydroxy group and a C1 to C4 alkoxy group), a C1 to C4 alkoxy group (which may be substituted by a group selected from the group consisting of a hydroxy group, a C1 to C4 alkoxy group, a sulfo group and a carboxy group), an acylamino group, an alkylsulfonylamino group or a phenylsulfonylamino group (the phenyl group may be substituted by a group selected from the group consisting of a halogen atom, an alkyl group and a nitro group),

each of R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸ R²⁹ and R²⁰ independently represents a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a carboxy group, a sulfo group, a sulfamoyl group, an N-alkylaminosulfonyl group, an N-phenylaminosulfonyl group), a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group), a phosphono group, a nitro group, an acyl group, a ureide group, a C1 to C4 alkyl group (which may be substituted by a hydroxy group or a C1 to C4 alkoxy group), a C1 to C4 alkoxy group (which may be substituted by a hydroxy group, a C1 to C4 alkoxy group, a sulfo group or a carboxy group), an acylamino group, an alkylsulfonylamino group or a phenylsulfonylamino group (the phenyl group may be substituted by a halogen atom, an alkyl group or a nitro group),

n represents 0 or 1,

respectively).

23. The water-based black ink composition according to claim 20, wherein (b) a dye having a maximum absorption wavelength in the range of 350 nm to 550 nm and (c) a dye having a maximum absorption wavelength in the range of 560 nm to 660 nm are the compound represented by the formula (5) or the salt thereof described in claim 21 and a compound represented by the formula (II-2).or a salt thereof, respectively,

Formula (II-2):

{wherein, each of R¹²¹ and R¹²² independently represents a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a sulfo group, a sulfamoyl group, an N-alkylaminosulfonyl group, an N-phenylaminosulfonyl group, a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group), a phosphono group, a nitro group, an acyl group, a ureide group, a C1 to C4 alkyl group (which may be substituted by a hydroxy group or a C1 to C4 alkoxy group), a C1 to C4 alkoxy group (which may be substituted by a hydroxy group, a C1 to C4 alkoxy group, a sulfo group or a carboxy group), an acylamino group, an alkylsulfonylamino group or a phenylsulfonylamino group (the phenyl group may be substituted by a halogen atom, an alkyl group or a nitro group),

m represents 0 or 1,

n represents 0 or 1, and

X represents a sulfo group,

the group B′

represents the following formula (II-3) or (II-4)

(wherein, each of R¹²³, R¹²⁴, R¹²⁵, R¹²⁶, R¹²⁷ and R¹²⁸ independently represents a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a carboxy group, a sulfo group, a sulfamoyl group, an N-alkylaminosulfonyl group, an N-phenylaminosulfonyl group, a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group), a phosphono group, a nitro group, an acyl group, a ureide group, a C1 to C4 alkyl group (which may be substituted by a hydroxy group or a C1 to C4 alkoxy group), a C1 to C4 alkoxy group (which may be substituted by a group selected from the group consisting of a hydroxy group, a C1 to C4 alkoxy group, a sulfo group or a carboxy group), an acylamino group, an alkylsulfonylamino group or a phenylsulfonylamino group (the phenyl group may be substituted by a group selected from the group consisting of a halogen atom, alkyl group or a nitro group)),

the group C′

is a substituted phenyl group or a substituted naphthyl group, and said phenyl or naphthyl group has a group selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, a carboxy group, a sulfo group, a sulfamoyl group, an N-alkylaminosulfonyl group, an N-phenylaminosulfonyl group, a C1 to C4 alkylsulfonyl group (which may be substituted by a hydroxy group), a phosphono group, a nitro group, an acyl group, a ureide group, a C1 to C4 alkyl group (which may be substituted by a hydroxy group or a C1 to C4 alkoxy group), a C1 to C4 alkoxy group (which may be substituted by a group selected from the group consisting of a hydroxy group, a C1 to C4 alkoxy group, a sulfo group and a carboxy group), an acylamino group, an alkylsulfonylamino group and a phenylsulfonylamino group (the phenyl group may be substituted by a group selected from the group consisting of a halogen atom, an alkyl group or a nitro group), as a substituent), respectively}.