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Coloring composition, ink for ink jet, and ink jet recording method Number:6,734,225 from the United States Patent and Trademark Office (PTO) owispatent

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Title: Coloring composition, ink for ink jet, and ink jet recording method

Abstract: An ink for an ink jet includes a coloring composition comprising a dispersion medium and coloring particulates containing an oil-soluble dye represented by formula (1) and a polymer selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates. The formula (1) satisfies at least one of following (i) to (v): (i) A represents --NR.sup.4 R.sup.5, R.sup.4 and R.sup.5 each represents independently a C.sub.1-18 alkyl group having a substituent group; (ii) At least one of R.sup.2 and R.sup.7 represents a substituted alkyl group; (iii) R.sup.8 represents an aryl group having two or more substituent groups; (iv) Two or more substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171 are present in the molecule; and (v) One or more carboxyl groups are present in the molecule. ##STR1##

Patent Number: 6,734,225 Issued on 05/11/2004 to Yamanouchi,   et al.


Inventors: Yamanouchi; Junichi (Kanagawa, JP), Kimura; Keizo (Kanagawa, JP), Ishizuka; Takahiro (Kanagawa, JP)
Assignee: Fuji Photo Film Co., Ltd. (Minami-Ashigara, JP)
Appl. No.: 09/780,402
Filed: February 12, 2001


Foreign Application Priority Data

Feb 15, 2000 [JP] 2000-036547
Sep 04, 2000 [JP] 2000-266964

Current U.S. Class: 523/160 ; 524/102; 524/589; 524/601; 524/91; 524/94; 524/99
Current International Class: C09B 55/00 (20060101); C09B 67/20 (20060101); C09B 67/00 (20060101); C09B 67/46 (20060101); C09D 11/00 (20060101)
Field of Search: 523/160,161 106/31.43,31.46,31.49,31.47 524/86,87,91,94,99,102,106,589,601


References Cited [Referenced By]

U.S. Patent Documents
5508421 April 1996 Suzuki et al.
5612282 March 1997 Komamura et al.
6025412 February 2000 Sacripante et al.
6031019 February 2000 Tsutsumi et al.
6313196 November 2001 Helling et al.
Foreign Patent Documents
56-157468 Dec., 1981 JP
58-45272 Mar., 1983 JP
03231975 Oct., 1991 JP
4-18468 Jan., 1992 JP
6-340835 Dec., 1994 JP
7-268254 Oct., 1995 JP
7-268257 Oct., 1995 JP
7-268260 Oct., 1995 JP
8-183920 Jul., 1996 JP
9-59552 Mar., 1997 JP
9-111163 Apr., 1997 JP
9-255887 Sep., 1997 JP
10-36728 Feb., 1998 JP
10-110126 Apr., 1998 JP
10-195355 Jul., 1998 JP

Other References

English Translation of JP 09059552 (1997).* .
English Translation of JP 030231975 (1990)..

Primary Examiner: Shosho; Callie
Attorney, Agent or Firm: Burns, Doane, Swecker & Mathis, L.L.P.

Claims



What is claimed is:

1. An ink for an ink jet comprising a coloring composition comprising: (a) a dispersion medium; and (b) coloring particulates comprising: (b-1) a polymer which is selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and (b-2) an oil-soluble dye represented by formula (1): ##STR22## wherein R.sup.1 represents a hydrogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.11, --SR.sup.12, --CO.sub.2 R.sup.13, --OCOR.sup.14, --NR.sup.15 R.sup.16, --CONR.sup.17 R.sup.18, --SO.sub.2 R.sup.19, --SO.sub.2 NR.sup.20 R.sup.21, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26, --COR.sup.27, --NR.sup.28 COR.sup.29 or --NR.sup.30 SO.sub.2 R.sup.31, and R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein A represents --NR.sup.4 R.sup.5 or a hydroxyl group, and R.sup.4 and R.sup.5 each represents independently a hydrogen atom, aliphatic group, aromatic group or heterocyclic group; wherein B.sup.1 represents .dbd.C(R.sup.6)-- or .dbd.N-- and B.sup.2 represents --C(R.sup.7).dbd. or --N.dbd.; wherein R.sup.2, R.sup.3, R.sup.6 and R.sup.7 each represents independently a hydrogen atom, halogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.51, --SR.sup.52, --CO.sub.2 R.sup.53, --OCOR.sup.54, --NR.sup.55 R.sup.56, --CONR.sup.57 R.sup.58, --SO.sub.2 R.sup.59, --SO.sub.2 NR.sup.60 R.sup.61, --NR.sup.62 CONR.sup.63 R.sup.64, NR.sup.65 CO.sub.2 R.sup.66, --COR.sup.67, --NR.sup.68 COR.sup.69 or --NR.sup.70 SO.sub.2 R.sup.71, and R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.70 and R.sup.71 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, or R.sup.6 and R.sup.7 may be mutually bound to form a ring; wherein X and Y each represents independently C(R.sup.8).dbd. or N.dbd., R.sup.8 represents a hydrogen atom, aliphatic group or aromatic group, either X or Y shall represent N.dbd., and X and Y shall not be simultaneously --N.dbd.; and wherein the formula (1) two or more substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171 are present in the dye, and R.sup.170 and R.sup.171 each represents independently a hydrogen atom, aliphatic group or aromatic groups, and wherein the polymer and the oil-soluble dye are separate compounds.

2. An ink for an ink jet according to claim 1, wherein the oil-soluble dye is at least one compound represented by any one of formulae (2-1) to (2-5): ##STR23## wherein in the formulae (2-1) to (2-5) X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the same meanings as defined above in the formula (1); wherein in the formula (2-1) R.sup.201 and R.sup.202 each represents a C.sub.1-18 alkyl group having a substituent group, the substituent group is at least one member selected from the group consisting of a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161, and R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-2) R.sup.203 represents a C.sub.1-10 substituted alkyl group; wherein in the formulae (2-3a) and (2-3b), R.sup.204, R.sup.205, R.sup.206 and R.sup.207 each represents independently a cyano or a group having no more than C.sub.100 selected from the group consisting of an aliphatic group, aromatic group, heterocyclic group, --OR.sup.211, --SR.sup.212, --CO.sub.2 R.sup.213, --OCOR.sup.214, --NR.sup.215 R.sup.216, --CONR.sup.217 R.sup.218, --SO.sub.2 R.sup.219, --SO.sub.2 NR.sup.220 R.sup.221, --NR.sup.222 CONR.sup.223 R.sup.224, --NR.sup.225 CO.sub.2 R.sup.226, --COR.sup.227, --NR.sup.228 COR.sup.229 and --NR.sup.230 SO.sub.2 R.sup.231, and R.sup.211, R.sup.212, R.sup.213, R.sup.214, R.sup.215, R.sup.216, R.sup.217, R.sup.218, R.sup.219, R.sup.220, R.sup.221, R.sup.222, R.sup.223, R.sup.224, R.sup.225, R.sup.226, R.sup.227, R.sup.228, R.sup.229, R.sup.230 and R.sup.231 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-4) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272, two or more substituent groups represented by --NR.sup.271 SO.sub.272 are contained in the dye, and R.sup.271 and R.sup.272 each represents independently a hydrogen atom, aliphatic group or aromatic group; and wherein in the formula (2-5) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has one or more water-soluble groups.

3. An ink for an ink jet according to claim 1, wherein in the formula (1) R.sup.1 represents hydrogen, C.sub.1-6 alkyl group or C.sub.1-6 substituted alkyl group.

4. An ink for an ink jet according to claim 1, wherein in the formula (1) X is --N.dbd. and Y is --C(R.sup.8).dbd..

5. An ink for an ink jet according to claim 1, wherein in the formula (1) B.sup.1 is .dbd.C(R.sup.6)-- and B.sup.2 is --C(R.sup.7).dbd..

6. An ink for an ink jet according to claim 1, wherein the polymer includes 0.01 to 3.0 mmol/g of an ionic group.

7. An ink for an ink jet according to claim 1, wherein the polymer includes 0.01 to 3.0 mmol/g of a ionic group, and the coloring composition is formed by emulsifying and dispersing coloring particulates which contain said polymer and the oil-soluble dye represented by formula (1) in a water-based dispersion medium.

8. An ink for an ink jet according to claim 1, wherein the polymer contains at least one kind of ionic group selected from carboxyl groups and sulfonate groups.

9. An ink for an ink jet according to claim 1, wherein the polymer is polyurethane or polyester.

10. An ink for an ink jet according to claim 1, wherein the coloring particulates are obtained by emulsifying and making into fine particles an organic solvent which includes the polymer and the oil-soluble dye, by either adding water to the organic solvent, or adding the organic solvent into water.

11. An ink for an ink jet according to claim 1, wherein the ink has a wavelength of maximum absorption (.lambda..sub.max (nm)) in a wavelength range from 510 to 560 nm; and when absorbance at .lambda..sub.max is regarded as 1, the absorbance is no less than 0.2 at (.lambda..sub.max +75 nm), and the absorbance is no more than 0.4 at (.lambda..sub.max -75 nm).

12. An ink for an ink jet according to claim 11, wherein the absorbance is no less than 0.1 at (.lambda..sub.max +75 nm), and the absorbance is no more than 0.3 at (.lambda..sub.max -75 nm).

13. The ink for an ink jet according to claim 1, wherein R.sup.8 represents a substituted aryl group.

14. A coloring composition comprising: (a) a dispersion medium; and (b) coloring particulates comprising: (b-1) a polymer which is selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and (b-2) an oil-soluble dye represented by formula (1): ##STR24## wherein R.sup.1 represents a hydrogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.11, --SR.sup.12, --CO.sub.2 R.sup.13, --OCOR.sup.14, --NR.sup.15 R.sup.16, --CONR.sup.17 R.sup.18, --SO.sub.2 R.sup.19, --SO.sub.2 NR.sup.20 R.sup.21, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26 --COR.sup.27, --NR.sup.28 COR.sup.29 --NR.sup.30 SO.sub.2 R.sup.31, and R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein A represents --NR.sup.4 R.sup.5 or a hydroxyl group, and R.sup.4 and R.sup.5 each represents independently a hydrogen atom, aliphatic group, aromatic group or heterocyclic group; wherein B.sup.1 represents .dbd.C(R.sup.6)-- or .dbd.N-- and B.sup.2 represents --C(R.sup.7).dbd. or --N.dbd.; wherein R.sup.2, R.sup.3, R.sup.6 and R.sup.7 each represents independently a hydrogen atom, halogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.51, --SR.sup.52, --CO.sub.2 R.sup.53, --OCOR.sup.54, --NR.sup.55 R.sup.56, --CONR.sup.57 R.sup.58, --SO.sub.2 R.sup.59, SO.sub.2 NR.sup.60 R.sup.61, --NR.sup.62 CONR.sup.63 R.sup.64, --NR.sup.65 CO.sub.2 R.sup.66, --COR.sup.67, --NR.sup.68 COR.sup.69 --NR.sup.70 SO.sub.2 R.sup.71, and R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.70 and R.sup.71 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, or R.sup.6 and R.sup.7 may be mutually bound to form a ring; wherein X and Y each represents independently C(R.sup.8).dbd. or N.dbd., R.sup.8 represents a hydrogen atom, aliphatic group or aromatic group, either X or Y shall represent N.dbd., and X and Y shall not be simultaneously --N.dbd.; and wherein in the formula (1), two or more substituent groups represent by --NR.sup.170 SO.sub.2 R.sup.171 are present in the dye, and R.sup.170 and R.sup.171 each represent independently a hydrogen atom, aliphatic group or aromatic group, and wherein the polymer and oil-soluble dye are separate compounds.

15. A coloring composition according to claim 14, wherein the oil-soluble dye is at least one compound represented by any one of formulae (2-1) to (2-5): ##STR25## wherein in the formulae (2-1) to (2-5) X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the same meanings as defined above in the formula (1); wherein in the formula (2-1) R.sup.201 and R.sup.202 each represents a C.sub.1-18 alkyl group having a substituent group, the substituent group is at least one member selected from the group consisting of a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161, and R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-2) R.sup.203 represents a C.sub.1-10 substituted alkyl group; wherein in the formulae (2-3a) and (2-3b), R.sup.204, R.sup.205, R.sup.206 and R.sup.207 each represents independently a cyano or a group having no more than C.sub.100 selected from the group consisting of an aliphatic group, aromatic group, heterocyclic group, --OR.sup.211, --R.sup.212, --CO.sub.2 R.sup.213, --OCOR.sup.214, --NR.sup.215 R.sup.216, --CONR.sup.217 R.sup.218, --SO.sub.2 R.sup.219, --SO.sub.2 NR.sup.220 R.sup.221, --NR.sup.222 CONR.sup.223 R.sup.224, --NR.sup.225 CO.sub.2 R.sup.226, --COR.sup.227, --NR.sup.228 COR.sup.229 and --NR.sup.230 SO.sub.2 R.sup.231, and R.sup.211, R.sup.212, R.sup.213, R.sup.214, R.sup.215, R.sup.216, R.sup.217, R.sup.218, R.sup.219, R.sup.220, R.sup.221, R.sup.222, R.sup.223, R.sup.224, R.sup.225, R.sup.226, R.sup.227, R.sup.228, R.sup.229, R.sup.230 and R.sup.231 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-4) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272, two or more substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272 are contained in the dye, and R.sup.271 and R.sup.272 each represents independently a hydrogen atom, aliphatic group or aromatic group; and wherein in the formula (2-5) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has one or more water-soluble groups.

16. A coloring composition according to claim 14, wherein the coloring composition has a wavelength of maximum absorption (.lambda..sub.max (nm)) in a wavelength range from 510 to 560 nm; and when absorbance at .lambda..sub.max is regarded as 1, the absorbance is no less than 0.2 at (.lambda..sub.max +75 nm), and the absorbance is no more than 0.4 at (.lambda..sub.max -75 nm).

17. The coloring composition according to claim 14, wherein R.sup.8 represents a substituted aryl group.

18. An ink jet recording method comprising the steps of: (1) preparing an ink for an ink jet; and (2) using the ink for recording in an ink-jet printing device;

wherein the ink comprising a coloring composition comprising: (a) a dispersion medium; and (b) coloring particulates comprising: (b-1) a polymer which is selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and (b-2) an oil-soluble dye represented by formula (1): ##STR26## wherein R.sup.1 represents a hydrogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.11, --SR.sup.12, --CO.sub.2 R.sup.13, --OCOR.sup.14, --NR.sup.15 R.sup.16, --CONR.sup.17 R.sup.18, --SO.sub.2 R.sup.19, --SO.sub.2 NR.sup.20 R.sup.21, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26, --COR.sup.27, --NR.sup.28 COR.sup.29 or --NR.sup.30 SO.sub.2 R.sup.31, and R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein A represents --NR.sup.4 R.sup.5 or a hydroxyl group, and R.sup.4 and R.sup.5 each represents independently a hydrogen atom, aliphatic group, aromatic group or heterocyclic group; wherein B.sup.1 represents .dbd.C(R.sup.6)-- or .dbd.N-- and B.sup.2 represents --C(R.sup.7).dbd. or --N.dbd.; wherein R.sup.2, R.sup.3, R.sup.6 and R.sup.7 each represents independently a hydrogen atom, halogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.51, --SR.sup.52, --CO.sub.2 R.sup.53, --OCOR.sup.54, --NR.sup.55 R.sup.56, --CONR.sup.57 R.sup.58, --SO.sub.2 R.sup.59, --SO.sub.2 NR.sup.60 R.sup.61, --NR.sup.62 CONR.sup.63 R.sup.64, --NR.sup.65 CO.sub.2 R.sup.66, --COR.sup.67, --NR.sup.68 COR.sup.69 or --NR.sup.70 SO.sub.2 R.sup.71, and R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.70 and R.sup.71 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, or R.sup.6 and R.sup.7 may be mutually bound to form a ring; wherein X and Y each represents independently C(R.sup.8).dbd. or N.dbd., R.sup.8 represents a hydrogen atom, aliphatic group or aromatic group, either X or Y shall represent N.dbd., and X and Y shall not be simultaneously --N.dbd.; and wherein the formula (1), two or more substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171 are presented in the dye, and R.sup.170 and R.sup.171 each represents independently a hydrogen atom, aliphatic group or aromatic group, and wherein the polymer and the oil-soluble dye are separate compounds.

19. An ink jet recording method according to claim 18, wherein the oil-soluble dye is at least one compound represented by any one of formulae (2-1) to (2-5): ##STR27## wherein in the formulae (2-1) to (2-5) X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the same meanings as defined above in the formula (1); wherein in the formula (2-1) R.sup.201 and R.sup.202 each represents a C.sub.1-18 alkyl group having a substituent group, the substituent group is at least one member selected from the group consisting of a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161, and R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-2) R.sup.203 represents a C.sub.1-10 substituted alkyl group; wherein in the formulae (2-3a) and (2-3b), R.sup.204, R.sup.205, R.sup.206 and R.sup.207 each represents independently a cyano or a group having no more than C.sub.100 selected from the group consisting of an aliphatic group, aromatic group, heterocyclic group, --OR.sup.211, --SR.sup.212, --CO.sub.2 R.sup.213, --OCOR.sup.214, --NR.sup.215 R.sup.216, --CONR.sup.217 R.sup.218, --SO.sub.2 R.sup.219, --SO.sub.2 NR.sup.220 R.sup.221, --NR.sup.222 CONR.sup.223 R.sup.224, --NR.sup.225 CO.sub.2 R.sup.226, --COR.sup.227, --NR.sup.228 COR.sup.229 and --NR.sup.230 SO.sub.2 R.sup.231, and R.sup.211, R.sup.212, R.sup.213, R.sup.214, R.sup.215, R.sup.216, R.sup.217, R.sup.218, R.sup.219, R.sup.220, R.sup.221, R.sup.222, R.sup.223, R.sup.224, R.sup.225, R.sup.226, R.sup.227, R.sup.228, R.sup.229, R.sup.230 and R.sup.231 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein in the formula (2-4) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272, two or more substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272 are contained in the dye, and R.sup.271 and R.sup.272 each represents independently a hydrogen atom, aliphatic group or aromatic group; and wherein in the formula (2-5) at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has one or more water-soluble groups.

20. An ink jet recording method according to claim 18, wherein the ink has a wavelength of maximum absorption (.lambda..sub.max (nm)) in a wavelength range from 510 to 560 nm; and when absorbance at .lambda..sub.max is regarded as 1, the absorbance is no less than 0.2 at (.lambda..sub.max +75 nm), and the absorbance is no more than 0.4 at (.lambda..sub.max -75 nm).

21. The ink jet recording method according to claim 18, wherein R.sup.8 represents a substituted aryl group.
Description



BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a water-based coloring composition containing an oil soluble dye (especially magenta dye), and to an ink for an ink jet which contains the coloring composition, and to an ink jet recording method using the ink for the ink jet. In particular, the present invention relates to a coloring composition whose color reproduction (especially magenta color reproduction) is good and which is suited for water based inks for writing, water based printing inks, inks for information recording, and the like, and to an ink for an ink jet which is suitable for a thermal, piezo-electric, electric field, or acoustic ink jet method, and to an ink jet recording method.

2. Description of the Related Art

In recent years, as use of computers has become more widespread, ink jet printers have become widely used not only in offices, but in homes as well, for printing on paper, film, cloth and the like. Oil based inks, water based inks, solid inks and the like are known as inks for ink jets. Among these, water based inks are advantageous from the standpoints of ease of production, usability, lack of odor, safety, and the like thereof, and therefore, water based inks are mainly used.

However, most water based inks use a water soluble dye which dissolves when in a molecular state. Thus, although there are great advantages with regard to transparency and color density, because the dye is water soluble, the water resistance thereof is poor. Problems arise in that when a water based ink is used for printing onto regular paper, bleeding occurs such that the quality of the printed product markedly deteriorates. Further, the light resistance is poor.

Water based inks using pigments or dispersed dyes in order to overcome these problems are proposed in, for example, Japanese Patent Application Laid-Open (JP-A) Nos. 56-157468, 4-18468, 8-183920, 10-110126, 10-195355 and the like.

However, with these water based inks, although the water resistance is improved to a certain extent, it is still insufficient. There are further problems in that the storage stability of the dispersion of the dispersed dye or pigment within the water based ink is lacking, and it is easy for clogging of the ink discharge ports to occur. Further, with these water based inks, generally, a sufficient hue cannot be obtained, and in particular, the hue of the cyan component is insufficient. Problems in color reproduction arise due to the insufficient color tone.

JP-A Nos. 58-45272, 6-340835, 7-268254, 7-268257, and 7-268260 disclose a method of encapsulating a dye in urethane or polyester dispersion particles.

However, in such cases, the color reproduction is insufficient due to the insufficient color tone. Further, the dispersion stability and water resistance of the dye encapsulating polymer substance, when a dye is encapsulated to a desired concentration, are not always sufficient.

JP-A Nos. 9-59552, 9-111163, 9-255887, and 10-36728 propose improving the color tone by using a colorant in which an aromatic diamine is coupled with a pyrazolotriazole.

However, in these cases, there are problems in that the color tone changes depending on the type of image receiving paper, and the water resistance is insufficient.

SUMMARY OF THE INVENTION

The present invention overcomes the above-described drawbacks, and achieves the following objects. The present invention provides a coloring composition which has excellent dispersion stability of the coloring particulates, has excellent color forming property and excellent color tone (especially magenta color reproduction) when printing onto any type of paper regardless of the paper type, has excellent water resistance and light resistance, and is suitable for use as a water based ink for writing, a water based printing ink, an ink for information recording, or the like. The present invention also provides an ink for an ink jet which is suited for a thermal, piezo-electric, electric field or acoustic ink jet method, which does not cause clogging of a nozzle tip when printing is carried out using nozzles, and which has excellent color forming property and excellent color tone (especially magenta color reproduction) when printing onto any type of paper regardless of paper type, and has excellent water resistance and light resistance, and to an ink jet recording method.

In a first aspect of the present invention, there is provided an ink for an ink jet, said ink comprising a coloring composition comprising a dispersion medium and coloring particulates comprising a polymer which is selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and an oil-soluble dye represented by formula (1): ##STR2## wherein R.sup.1 represents a hydrogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.11, --SR.sup.12, --CO.sub.2 R.sup.13, --OCOR.sup.14, --NR.sup.15 R.sup.16, --CONR.sup.17 R.sup.18, --SO.sub.2 R.sup.19, --SO.sub.2 NR.sup.20 R.sup.21, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26, --COR.sup.27, --NR.sup.28 COR.sup.29 or --NR.sup.30 SO.sub.2 R.sup.31, and R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein A represents --NR.sup.4 R.sup.5 or a hydroxyl group, and R.sup.4 and R.sup.5 each represents independently a hydrogen atom, aliphatic group, aromatic group or heterocyclic group; wherein B.sup.1 represents .dbd.C(R.sup.6)-- or .dbd.N-- and B.sup.2 represents --C(R.sup.7).dbd. or --N.dbd.; wherein R.sup.2, R.sup.3, R.sup.6 and R.sup.7 each represents independently a hydrogen atom, halogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.51, --SR.sup.52, --CO.sub.2 R.sup.53, --OCOR.sup.54, --NR.sup.55 R.sup.56, --CONR.sup.57 R.sup.58, --SO.sub.2 R.sup.59, --SO.sub.2 NR.sup.60 R.sup.61, --NR.sup.62 CONR.sup.63 R.sup.64, --NR.sup.65 CO.sub.2 R.sup.66, --COR.sup.67, --NR.sup.68 COR.sup.69 or --NR.sup.70 SO.sub.2 R.sup.71, and R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.70 and R.sup.71 each represents independently a hydrogen atom, aliphatic group or aromatic group; wherein R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, or R.sup.6 and R.sup.7 may be mutually bound to form a ring; wherein X and Y each represents independently C(R.sup.8).dbd. or N.dbd., R.sup.8 represents a hydrogen atom, aliphatic group or aromatic group, either X or Y shall represent N.dbd., and X and Y shall not be simultaneously --N.dbd.; and wherein the formula (1) satisfies at least one of following (i) to (v): (i) A represents --NR.sup.4 R.sup.5, R.sup.4 and R.sup.5 each represents independently a C.sub.1-18 alkyl group having a substituent group, the substituent group is at least one member selected from the group consisting of a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161, and R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group; (ii) R.sup.2 represents a substituted alkyl group; (ii)' R.sup.7 represents a substituted alkyl group; (iii) R.sup.8 represents an aryl group having 2 or more substituent groups; (iv) Two or more substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171 are present in the molecule, and R.sup.170 and R.sup.171 each represents independently a hydrogen atom, aliphatic group or aromatic group; and (v) One or more carboxyl groups are present in the molecule.

In a second aspect of the present invention, there is provided a coloring composition, said coloring composition comprising a dispersion medium and coloring particulates comprising a polymer which is selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and an oil-soluble dye represented by said formula (1).

In a third aspect of the present invention, there is provided an ink jet recording method, said method comprising the steps of (a) preparing an ink for an ink jet and (b) using the ink for recording in an ink-jet printing device, wherein the ink comprising a coloring composition comprising a dispersion medium and coloring particulates containing a polymer selected from the group consisting of polyurethanes, polyesters, polyamides, polyureas and polycarbonates; and an oil-soluble dye represented by said formula (1).

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The coloring composition, the ink for an ink jet, and the ink jet recording method of the present invention will be described hereinafter.

[Coloring Composition]

The coloring composition of the present invention comprises coloring particulates containing an oil-soluble dye and a polymer dispersed in a dispersion medium. The dispersion medium is preferably a water-based medium. The water-based medium means a liquid containing at least water.

Oil-soluble Dye

The oil-soluble dye is preferably a compound represented by formula (1). ##STR3##

In the formula (1) above, R.sup.1 represents a hydrogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.11, --SR.sup.12, --CO.sub.2 R.sup.13, --OCOR.sup.14, --NR.sup.15 R.sup.16, --CONR.sup.17 R.sup.18, --SO.sub.2 R.sup.19, --SO.sub.2 NR.sup.20 R.sup.21, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26, --COR.sup.27, --NR.sup.28 COR.sup.29 or --NR.sup.30 SO.sub.2 R.sup.31 ; and R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29, R.sup.30 and R.sup.31 each represents independently a hydrogen atom, aliphatic group or aromatic group.

In particular, R.sup.1 is preferably a hydrogen atom, aliphatic group, aromatic group, --OR.sup.11, --SR.sup.12, --NR.sup.15 R.sup.16, --SO.sub.2 R.sup.19, --NR.sup.22 CONR.sup.23 R.sup.24, --NR.sup.25 CO.sub.2 R.sup.26, --NR.sup.28 COR.sup.29 or --NR.sup.30 SO.sub.2 R.sup.31, more preferably a hydrogen atom, aliphatic group, aromatic group, --OR.sup.11 or --NR.sup.15 R.sup.16, further preferably a hydrogen atom, alkyl group, substituted alkyl group, aryl group, substituted aryl group, alkoxy group, substituted alkoxy group, phenoxy group, substituted phenoxy group, dialkyl anino group or substituted dialkyl amino group, particularly preferably a hydrogen atom, C.sub.1-10 alkyl group, C.sub.1-10 substituted alkyl group, C.sub.6-10 aryl group or C.sub.6-10 substituted aryl group, most preferably a hydrogen atom, C.sub.1-6 alkyl group or C.sub.1-6 substituted alkyl group.

The aliphatic group includes an alkyl group, substituted alkyl group, alkenyl group, substituted alkenyl group, alkynyl group, substituted alkynyl group, aralkyl group and substituted aralkyl group.

The alkyl group may be straight-chain or branched one or may have formed a ring. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 18.

The alkyl moiety in the substituted alkyl group is the same as the above-defined alkyl group.

The alkenyl group may be straight-chain or branched one or may have formed a ring. The number of carbon atoms in the alkenyl group is preferably 2 to 20, more preferably 2 to 18.

The alkenyl moiety in the substituted alkenyl group is the same as the above-defined alkenyl group.

The alkynyl group may be straight-chain or branched one or may have formed a ring. The number of carbon atoms in the alkynyl group is preferably 2 to 20, more preferably 2 to 18.

The alkynyl moiety in the substituted alkynyl group is the same as the above-defined alkynyl group.

The alkyl moiety in the aralkyl group and substituted aralkyl group is the same as the above-defined alkyl group. The aryl moiety in the aralkyl group and substituted aralkyl group is preferably phenyl or naphthyl, particularly preferably phenyl.

Substituent groups on the alkyl moieties in the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group described above include e.g. a halogen atom, cyano, nitro, heterocyclic group, --OR.sup.111, --SR.sup.112, --CO.sub.2 R.sup.113, --NR.sup.114 R.sup.115, --CONR.sup.116 R.sup.117, --SO.sub.2 R.sup.118 and --SO.sub.2 NR.sup.119 R.sup.120 etc. R.sup.111, R.sup.112, R.sup.113, R.sup.114, R.sup.115, R.sup.116, R.sup.117, R.sup.118, R.sup.119 and R.sup.120 each represents independently a hydrogen atom, aliphatic group or aromatic group. Substituent groups on the aryl moiety in the substituted aralkyl group include a halogen atom, cyano, nitro, aliphatic group, heterocyclic group, --OR.sup.121, --SR.sup.122, --CO.sub.2 R.sup.123, --NR.sup.124 R.sup.125, --CONR.sup.126 R.sup.127, --SO.sub.2 R.sup.128 or --SO.sub.2 NR.sup.129 R.sup.130 etc. R.sup.121, R.sup.122, R.sup.123, R.sup.124, R.sup.125, R.sup.126, R.sup.127, R.sup.128, R.sup.129 and R.sup.130 each represents independently a hydrogen atom, aliphatic group or aromatic group.

The aromatic group includes to an aryl group and substituted aryl group. The aryl group is preferably phenyl or naphthyl, particularly preferably phenyl.

The aryl moiety in the substituted aryl group is the same as above-defined aryl group.

The heterocyclic group preferably includes 5- or 6-memberred saturated or unsaturated heterocyclic groups, and these heterocyclic groups may further have an aliphatic ring, aromatic ring or other heterocyclic ring condensed therewith.

Examples of heteroatoms in the heterocyclic ring include B, N, O, S, Se and Te. The heteroatoms are preferably N, O and S.

The heterocyclic ring is preferably a ring whose carbon atom has free valence (monovalence) (the heterocyclic group is bound at the carbon atom).

Examples of the saturated heterocyclic ring include a pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolan ring, and 1,3-thiazolidine ring.

Examples of the unsaturated heterocyclic ring include an imnidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.

The heterocyclic group may have a substituent group, and the substituent group includes e.g. a halogen atom, cyano, nitro, aliphatic group, aromatic group, heterocyclic group, --OR.sup.131, --SR.sup.132, --CO.sub.2 R.sup.133, --NR.sup.134 R.sup.135, --CONR.sup.136 R.sup.137, --SO.sub.2 R.sup.138 and --SO.sub.2 NR.sup.139 R.sup.140 etc. R.sup.131, R.sup.132, R.sup.133, R.sup.134, R.sup.135, R.sup.136, R.sup.137, R.sup.138, R.sup.139 and R.sup.140 each represents independently a hydrogen atom, aliphatic group or aromatic group.

In the formula (1) above, A represents --NR.sup.4 R.sup.5 or a hydroxyl group. A is preferably --NR.sup.4 R.sup.5.

In the formula (1) above, R.sup.4 and R.sup.5 each represents independently a hydrogen atom, aliphatic group, aromatic group or heterocyclic group. In particular, each of R.sup.4 and R.sup.5 is preferably a hydrogen atom or aliphatic group, more preferably a hydrogen atom, alkyl group or substituted alkyl group, particularly preferably a hydrogen atom, C.sub.1-18 alkyl group or C.sub.1-18 substituted alkyl group.

In particular, R.sup.4 and R.sup.5 each preferably represents independently a C.sub.1-18 alkyl group having a substituent group, and the substituent group is more preferably at least one member selected from a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161. Here, R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group.

Among substituent groups on R.sup.4 and R.sup.5, more preferable substituent groups are at least one member selected from cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161, particularly preferably at least one member selected from cyano, --OR.sup.141, --CO.sub.2 R.sup.143, --OCOR.sup.144 and --NR.sup.160 SO.sub.2 R.sup.161. When the substituent groups are --OR.sup.141, the number of such substituent groups in both R.sup.4 and R.sup.5 is 2 or more, preferably 2 to 4, and more preferably the number of such substituent groups in each of R.sup.4 and R.sup.5 is 2 or more. The most preferable substituent groups on R.sup.4 and R.sup.5 are at least one member selected from cyano and --CO.sub.2 R.sup.143.

In the formula (1) above, B.sup.1 represents .dbd.C(R.sup.6)-- or .dbd.N--, and B.sup.2 represents --C(R.sup.7).dbd. or --N.dbd.. In particular, it is preferable that B.sup.1 and B.sup.2 are simultaneously not --N.dbd., and it is more preferable that B.sup.1 is .dbd.C(R.sup.6)-- and simultaneously B.sup.2 is --C(R.sup.7).dbd..

R.sup.2, R.sup.3, R.sup.6 and R.sup.7 each represents independently a hydrogen atom, halogen atom, aliphatic group, aromatic group, heterocyclic group, cyano, --OR.sup.51, --SR.sup.52, --CO.sub.2 R.sup.53, --OCOR.sup.54, --NR.sup.55 R.sup.56, --CONR.sup.57 R.sup.58, --SO.sub.2 R.sup.59, --SO.sub.2 NR.sup.60 R.sup.61, --NR.sup.62 CONR.sup.63 R.sup.64, --NR.sup.65 CO.sub.2 R.sup.66, COR.sup.67, NR.sup.68 COR.sup.69 or --NR.sup.70 SO.sub.2 R.sup.71. R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.70 and R.sup.71 each represents independently a hydrogen atom, aliphatic group or aromatic group.

In particular, each of R.sup.2 and R.sup.7 is preferably a hydrogen atom, halogen atom, aliphatic group, --OR.sup.51, --NR.sup.62 CONR.sup.63 R.sup.64, --NR.sup.65 CO.sub.2 R.sup.66, --NR.sup.68 COR.sup.69 or --NR.sup.70 SO.sub.2 R.sup.71, more preferably a hydrogen atom, fluorine atom, chlorine atom, alkyl group, substituted alkyl group, --NR.sup.62 CONR.sup.63 R.sup.64 or --NR.sup.68 COR.sup.69, more preferably a hydrogen atom, chlorine atom, C.sub.1-10 alkyl group or C.sub.1-10 substituted alkyl group, most preferably a hydrogen atom, C.sub.1-4 alkyl group or C.sub.1-4 substituted alkyl group.

In particular, each of R.sup.2 and R.sup.7 is preferably a substituent alkyl group, more preferably a trifluoromethyl group. A substituent group on the substituted alkyl group are preferably a halogen atom, more preferably a fluorine atom.

Each of R.sup.3 and R.sup.6 is preferably a hydrogen atom, halogen atom or aliphatic group, more preferably a hydrogen atom, fluorine atom, chlorine atom, alkyl group or substituted alkyl group, further preferably a hydrogen atom, chlorine atom, C.sub.1-10 alkyl group or substituted C.sub.1-10 alkyl group, most preferably a hydrogen atom, C.sub.1-4 alkyl group, or C.sub.1-4 substituted alkyl group.

R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, R.sup.5 and R.sup.6, or R.sup.6 and R.sup.7 may be mutually bound to form a ring. The combination of R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, or R.sup.5 and R.sup.6 is preferable for forming a ring.

The ring formed by R.sup.2 and R.sup.3 or R.sup.6 and R.sup.7 is preferably a 5- or 6-memberred ring, and the ring is preferably an aromatic ring (e.g., a benzene ring) or an unsaturated heterocyclic ring (e.g., a pyridine ring, imidazole ring, thiazole ring, pyrimidine ring, pyrrole ring and furan ring).

The ring formed by R.sup.3 and R.sup.4 or R.sup.5 and R.sup.6 is preferably a 5- or 6-memberred ring, and the ring includes a tetrahydroquinoline ring and dihydroindole ring.

The ring formed by R.sup.4 and R.sup.5 is preferably a 5- or 6-memberred ring, and the ring includes a pyrrolidine ring, piperidine ring or morpholine ring.

X and Y each represents independently C(R.sup.8).dbd. or N.dbd.. Either X or Y shall represent N.dbd., and X and Y shall not be simultaneously --N.dbd.. The combination of X and Y is more preferably a combination wherein X is --N.dbd. and Y is --C(R.sup.8).dbd..

R.sup.8 represents a hydrogen atom, aliphatic group or aromatic group, and is preferably a hydrogen atom, alkyl group, substituted alkyl group, aryl group or substituted aryl group, more preferably a hydrogen atom, C.sub.1-150 substituted alkyl group or C.sub.6-150 substituted aryl group, most preferably C.sub.1-100 substituted alkyl group or C.sub.6-100 substituted aryl group. When R.sup.8 is a substituted aryl group, it preferably has two or more substituent groups and is more preferably a 3,4- or 3,5-disubstituted phenyl group, particularly preferably a 3,5-disubstituted phenyl group.

The oil-soluble dye represented by the formula (1) above has 2 or more substituent groups per molecule of the dye, more preferably 2 to 5 substituent groups and most preferably 2 to 3 substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171. R.sup.170 and R.sup.171 each represents independently a hydrogen atom, aliphatic group or aromatic group. In particular, R.sup.170 is preferably a hydrogen atom or aliphatic group, particularly preferably a hydrogen atom.

The oil-soluble dye represented by the formula (1) above also has preferably one or more water-soluble groups in the molecule. The water-soluble groups include ionic hydrophilic groups such as carboxyl group, quaternary ammonium group and sulfonic acid group, among which the carboxyl group is particularly preferable.

The oil-soluble dye represented by the formula (1) described above in the present invention satisfies at least one of (i) to (v) below: (i) A represents --NR.sup.4 R.sup.5, and R.sup.4 and R.sup.5 each represents independently a C.sub.1-18 alkyl group having a substituent group, and the substituent group is at least one member selected from a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161 ; and R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group; (ii) R.sup.2 represents a substituted alkyl group; (ii)' R.sup.7 represents a substituted alkyl group; (iii) R.sup.8 is an aryl group having 2 or more substituent groups (these substituent groups refer to substituent groups on the aryl group); (iv) Two or more substituent groups represented by --NR.sup.170 SO.sub.2 R.sup.171 are present in the molecule, and R.sup.170 and R.sup.171 each represents independently a hydrogen atom, aliphatic group or aromatic group; and (v) One or more carboxyl groups are present in the molecule.

The compounds represented by the formula (1) above are preferably those represented by any one of the formulae (2-1) to (2-5). ##STR4##

In the formulae (2-1) to (2-5), X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the same meanings as defined above in the formula (1). In the formulae (2-1), (2-2), (2-4) and (2-5), it is more preferable that X is --N.dbd. and Y is --C(R.sup.8).dbd., and the formula (2-3a) is more preferable than (2-3b).

In the formula (2-1) above, R.sup.201 and R.sup.202 each represents independently a C.sub.1-18 alkyl group having a substituent group, and the substituent group is at least one member selected from a heterocyclic group, cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --NR.sup.145 R.sup.146, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 and --NR.sup.160 SO.sub.2 R.sup.161. Here, R.sup.141, R.sup.142, R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.150, R.sup.151, R.sup.152, R.sup.153, R.sup.154, R.sup.155, R.sup.156, R.sup.157, R.sup.158, R.sup.159, R.sup.160 and R.sup.161 each represents independently a hydrogen atom, aliphatic group or aromatic group.

The substituent groups on R.sup.201 an R.sup.202 are preferably cyano, --OR.sup.141, --SR.sup.142, --CO.sub.2 R.sup.143, --OCOR.sup.144, --CONR.sup.147 R.sup.148, --SO.sub.2 R.sup.149, --SO.sub.2 NR.sup.150 R.sup.151, --NR.sup.152 CONR.sup.153 R.sup.154, --NR.sup.155 CO.sub.2 R.sup.156, --COR.sup.157, --NR.sup.158 COR.sup.159 or --NR.sup.160 SO.sub.2 R.sup.161, more preferably cyano, --OR.sup.141, --CO.sub.2 R.sup.143, --OCOR.sup.144 or --NR.sup.160 SO.sub.2 R.sup.161, particularly preferably cyano or --CO.sub.2 R.sup.143. When the substituent groups are --OR.sup.141, the number of such substituent groups in both R.sup.201 and R.sup.202 is 2 or more, preferably 2 to 4, and more preferably the number of such substituent groups in each of R.sup.201 and R.sup.202 is 2 or more.

In the formula (2-2) above, R.sup.203 represents a C.sub.1-10 substituted alkyl group. The substituted alkyl group is preferably a C.sub.1-4 substituted alkyl group, more preferably a trifluoromethyl group. The substituent group is preferably a halogen atom, more preferably a fluorine atom.

In the formulae (2-3a) and (2-3b) above, R.sup.204, R.sup.205, R.sup.206 and R.sup.207 each represents independently a cyano or a group having no more than C.sub.100 selected from the group consisting of an aliphatic group, aromatic group, heterocyclic group, --OR.sup.241, --SR.sup.242, --CO.sub.2 R.sup.243, --OCOR.sup.244, --NR.sup.245 R.sup.246, --CONR.sup.247 R.sup.248, --SO.sub.2 R.sup.249, --SO.sub.2 NR.sup.250 R.sup.251, --NR.sup.252 CONR.sup.253 R.sup.254, --NR.sup.255 CO.sub.2 R.sup.256, --COR.sup.257, --NR.sup.258 COR.sup.259 and --NR.sup.260 SO.sub.2 R.sup.261. The number of carbon atoms in the aliphatic group is preferably 50 or less. R.sup.241, R.sup.242, R.sup.243, R.sup.244, R.sup.245, R.sup.246, R.sup.247, R.sup.248, R.sup.249, R.sup.250, R.sup.251, R.sup.252, R.sup.253, R.sup.254, R.sup.255, R.sup.256, R.sup.257, R.sup.258, R.sup.259, R.sup.260 and R.sup.261 each represents independently a hydrogen atom, aliphatic group or aromatic group. In particular, R.sup.204, R.sup.205, R.sup.206 and R.sup.207 are preferably a group having no more than C.sub.30 selected from the group consisting of an aliphatic group, aromatic group, heterocyclic group, --OR.sup.241, --CO.sub.2 R.sup.243, --OCOR.sup.244, --CONR.sup.247 R.sup.248, --SO.sub.2 NR.sup.250 R.sup.251, --NR.sup.252 CONR.sup.253 R.sup.254, --NR.sup.255 CO.sub.2 R.sup.256, --COR.sup.257, --NR.sup.258 COR.sup.259 and --NR.sup.260 SO.sub.2 R.sup.261. Further, R.sup.204, R.sup.205, R.sup.206 and R.sup.207 are more preferably a group having no more than C.sub.30 selected from the group consisting of an aliphatic group, --OR.sup.241, --CO.sub.2 R.sup.243, --OCOR.sup.244, --CONR.sup.247 R.sup.248, --NR.sup.258 COR.sup.259 and --NR.sup.260 SO.sub.2 R.sup.261.

In the formula (2-4) above, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 or R.sup.8 has substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272, and two or more substituent groups represented by --NR.sup.271 SO.sub.2 R.sup.272 are contained in the molecule. The number of the --NR.sup.271 SO.sub.2 R.sup.272 groups in the molecule is preferably 2 to 5, more preferably 2 to 3. R.sup.271 and R.sup.272 each represents independently a hydrogen atom, aliphatic group or aromatic group. R.sup.271 is preferably a hydrogen atom or aliphatic group, particularly preferably a hydrogen atom.

In the formula (2-5) above, at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 has one or more water-soluble groups. The water-soluble groups include e.g. ionic hydrophilic groups such as carboxyl group, quaternary ammonium group and sulfonic acid group, among which the carboxyl group is particularly preferable.

Use of those compounds represented by any one of the formulae (2-1), (2-2), (2-3a), (2-3b), (2-4) and (2-5) above in one embodiment is preferable for dispersion stability with time. Use of those compounds represented by the formula (2-1) above in the another embodiment is preferably for lower absorption at 600 nm and advantageous for reducing smears on paper upon printing. Use of those compounds represented by the formula (2-2) above in another embodiment is preferable for achieving images superior in heat resistance. Use of those compounds represented by the formulae (2-3a) and (2-3b) above in another embodiment preferable for attaining sharp hues excellent in spectral absorption characteristics. Use of those compounds represented by the formula (2-4) above in another embodiment is preferable for dispersion stability and thermostability. Use of those compounds represented by the formula (2-5) above in another embodiment is preferable for attaining a dispersion of small particles.

Hereinafter, the examples (I-1 to I-53) of those compounds (azomethine coloring matter) represented by the formula (1) above are enumerated. ##STR5## ##STR6## ##STR7## ##STR8## ##STR9## ##STR10## ##STR11## ##STR12## ##STR13##

Among the compounds described above, those of the formula (2-1) above include (I-2), (I-3), (I-4), (I-5), (I-6), (I-7), (I-8), (I-10), (I-13), (I-14), (I-16), (I-17), (I-19), (I-20), (I-22), (I-23), (I-24), (I-29), (I-31), (I-32), (I-33), (I-38), (I-39), (I-41) and (I-42). The compounds of the formula (2-2) above include (I-3), (I-46), (I-47), (I-48) and (I-49). The compounds of the formulae (2-3a) and (2-3b) above include (I-12), (I-15), (I-21), (I-30), (I-37), (I-43), (I-44), (I-47), (I-49) and (I-52). The compounds of the formula (2-4) above include (I-1), (I-3), (I-4), (I-5), (I-11), (I-13), (I-15), (I-18), (I-21), (I-22), (I-24), (I-25), (I-26), (I-27), (I-28), (I-30), (I-32), (I-34), (I-35), (I-36), (I-40), (I-44), (I-45), (I-50), (I-51), (I-52) and (I-53). The compounds of the formula (2-5) above include (I-9), (I-12), (I-50) and (I-51).

The compounds (azomethine coloring matter) represented by formula (1) above can be synthesized according to a method described in e.g. JP-A 4-126772 and JP-B 7-94180. Those compounds of formula (1) wherein X is --N.dbd. and Y is --C(R.sup.8).dbd. can be synthesized according to a method described in e.g. JP-B 7-14941, JP-B 7-100705 and JP-A 3-184980. Further, those compounds of formula (1) wherein X is --C(R.sup.8).dbd. and Y is --N.dbd. can be synthesized according to a method described in e.g. JP-A 5-127328, JP-A 3-15842 and U.S. Pat. No. 3,725,067.

Polymer

The coloring composition contains a polymer selected from the group polyurethane, polyester, polyamide, polyurea and polycarbonate. These may be used singly or in combination thereof.

The polymer may be water-insoluble, water-dispersible (self-emulsifiable) or water-soluble, among which the water-dispersible polymer and the water-insoluble polymer are preferable for easy production; and the water-dispersible polymer is preferable for dispersion stability of coloring particulates.

The water-dispersible polymer may be an ionic polymer, a nonionic dispersible group-containing polymer, and a mixed polymer thereof.

The ionic polymer includes polymers having cationic groups such as tertiary amino group and quaternary ammonium group, as well as polymers having anionic groups in carboxylic acid, sulfonic acid etc.

The nonionic dispersible group-containing polymer includes polymers containing nonionic dispersible groups such as polyethylene oxy group.

Among these, the anionic group-containing ionic polymers, nonionic dispersible group-containing polymers and mixed polymers thereof are preferable for dispersion stability of coloring particulates.

Polyurethane

The polyurethane may be synthesized generally by polyaddition reaction of a diol compound with a diisocyanate compound as the starting materials.

The diol compound includes non-dissociable diols and ionic diols.

The non-dissociable diols include e.g. ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 2,2-dimethyl-1,3-propanediol, 1,2-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 3,3-dimethyl-1,2-butanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,2-diethyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 1,7-heptanediol, 2-methyl-2-propyl-1,3-propanediol, 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 1,2-octanediol, 1,8-octanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,4-cyclohexane dimethanol, hydroquinone, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol (average molecular weight=200, 300, 400, 600, 1000, 1500, 4000), polypropylene glycol (average molecular weight=200, 400, 1000), polyester polyol, 4,4'-dihydroxy-diphenyl-2,2-propane, and 4,4'-dihydroxyphenyl sulfone.

The ionic diols have ionic groups, and these are used for the purpose of imparting the ability to produce coloring particulates as well as the dispersion stability thereof.

Preferable examples of ionic groups in the ionic diols include anionic groups such as carboxyl group, sulfonic acid group, monosulfate group, --OPO(OH).sub.2, sulfinic acid group, and salts thereof (e.g., salts of alkali metals such as Na and K, ammonia, and ammonium salts such dimethylamine, ethanolamine, diethanolamine, triethanolamine and trimethylamine) and cationic groups such as primary, secondary, tertiary amine and quaternary ammonium salts.

Among these, the anionic groups are preferable among which the carboxyl group is particularly preferable.

The anionic group-containing diols described above include e.g. 2,2-bis(hydroxymethyl) propionic acid, 2,2-bis(hydroxymethyl) butanoic acid, 2,5,6-trimethoxy-3,4-dihydroxyhexanoic acid, 2,3-dihydroxy-4,5-dimethoxypentanoic acid and 3,5-di(2-hydroxy) ethyloxycarbonyl benzene sulfonic acid as well as salts thereof.

The diisocyanates described above include e.g. methylene diisocyanate, ethylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, 1,4-cyclohexane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,3-xylylene diisocyanate, 1,5-naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3'-dimethyl-4,4'-diphenyl methane diisocyanate, 3,3'-dimethyl biphenylene diisocyanate, 4,4'-biphenylene diisocyanate, dicyclohexyl methane diisocyanate, and methylenebis(4-cyclohexyl isocyanate).

As the diol compound and the diisocyanate compound each, one kind of compound may be used, or two or more kinds of compounds may be used in an arbitrary ratio depending on the objects (e.g. regulation of glass transition temperature (Tg) of the polymer, solubility thereof, compatibility thereof with dyes, and stability of the dispersion).

Polyester

The polyester above may be synthesized generally by dehydration condensation between a dicarboxylic acid compound and a diol compound.

The dicarboxylic acid compound includes e.g. ionic group-free dicarboxylic acids other than carboxylic acids and derivatives thereof, as well as ionic group-containing dicarboxylic acids other than carboxylic acids.

Preferable examples of the ionic group-free dicarboxylic acids other than carboxylic acids and derivatives thereof include oxalic acid, malonic acid, succinic ac


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