IP Library Granted Patent US 12,528,945
Granted Patent B2
US 12,528,945 · App. 17/672,694 · Granted Jan 20, 2026

Dye ink composition, cyan dye ink, dye ink for ink jet recording, ink jet recording method, and aqueous dye solution

Inventors: Keiichi Tateishi (Kanagawa, JP); Takashi Saitou (Kanagawa, JP); Yuta Takasaki (Kanagawa, JP); Yusuke Sakai (Kanagawa, JP)
Assignee: FUJIFILM Corporation
C09B67/0035C09B47/065C09B67/0016C09D11/037
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Quick Facts
Patent No.
US 12,528,945
App. No.
17/672,694
Granted
Jan 20, 2026
Kind
B2
Abstract

A dye ink composition includes: a compound A represented by the general formula (I-1) as defined herein; a compound B represented by the general formula (I-2) as defined herein; at least one of a compound C-I represented by the general formula (I-3-1) as defined herein or a compound C-II represented by the general formula (I-3-2) as defined herein; a compound D represented by the general formula (I-4) as defined herein; and water.

Claims (54)

1 . A dye ink composition comprising:

a compound A represented by the following general formula (I-1);

a compound B represented by the following general formula (I-2);

at least one of a compound C-I represented by the following general formula (I-3-1) or a compound C-II represented by the following general formula (I-3-2);

a compound D represented by the following general formula (I-4); and

water,

wherein, in the general formulae (I-1), (I-2), (I-3-1), (1-3-2), and (I-4), each Z 1 represents an alkyl group, an aryl group, or a heterocyclic group, the alkyl group, the aryl group, and the heterocyclic group having a substituent that has at least one ionic hydrophilic group; a plurality of Z 1 's in the general formulae (I-1), (I-2), (I-3-1), and (1-3-2) may be the same as or different from each other;

wherein, in the general formulae (I-2), (I-3-1), (1-3-2), and (I-4), each Z 2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; each Z 2 does not have an ionic hydrophilic group; and a plurality of Z 2 's in the general formulae (I-3-1), (1-3-2), and (I-4) may be the same as or different from each other; and

wherein, in the dye ink composition, in a case where a mass of the compound A is represented by W 1 , a mass of the compound B is represented by W 2 , a sum of a mass of the compound C-I and a mass of the compound C-II is represented by W 3 , a mass of the compound D is represented by W 4 , and a total sum of W 1 , W 2 , W 3 , and W 4 is represented by W A1 ,

a ratio of W 1 to W A1 is 6.0% to 35.0% by mass,

a ratio of W 2 to W A1 is 20.0% to 45.0% by mass,

a ratio of W 3 to W A1 is 15.0% to 45.0% by mass, and

a ratio of W 4 to W A1 is 1.0% to 30.0% by mass.

2 . The dye ink composition according to claim 1 , wherein Z 2 has at least one of a hydroxy group or a tertiary nitrogen atom.

3 . The dye ink composition according to claim 1 , wherein the ionic hydrophilic group is at least one of —SO 3 M, —CO 2 M, or —PO(OM) 2 wherein M represents a hydrogen atom or a counter cation.

4 . The dye ink composition according to claim 2 , wherein the ionic hydrophilic group is at least one of —SO 3 M, —CO 2 M, or —PO(OM) 2 wherein M represents a hydrogen atom or a counter cation.

5 . The dye ink composition according to claim 1 , wherein a ratio of W A1 to a total mass of the dye ink composition is 3.0% by mass or more and 5.5% by mass or less.

6 . The dye ink composition according to claim 2 , wherein a ratio of W A1 to a total mass of the dye ink composition is 3.0% by mass or more and 5.5% by mass or less.

7 . The dye ink composition according to claim 3 , wherein a ratio of W A1 to a total mass of the dye ink composition is 3.0% by mass or more and 5.5% by mass or less.

8 . The dye ink composition according to claim 1 , further comprising:

a compound represented by the following general formula (II),

wherein, in the general formula (II), Ar 20 represents a benzene ring or a naphthalene ring; R 21 to R 28 each independently represent a hydrogen atom or a substituent; R 21 and R 22 may be linked to each other to form a ring; R 23 and R 24 may be linked to each other to form a ring; R 25 and R 26 may be linked to each other to form a ring; R 27 and R 28 may be linked to each other to form a ring; R 29 represents a substituent; in a case where Ar 20 represents a benzene ring, k represents an integer of 0 to 4; in a case where Ar 20 represents a naphthalene ring, k represents an integer of 0 to 6; in a case where a plurality of R 29 's are present, the plurality of R 29 's may be the same as or different from each other; and in a case where a plurality of R 29 's are present, the plurality of R 29 's may be linked to each other to form a ring; and at least any one of R 21 to R 29 has a hydrophilic group.

9 . The dye ink composition according to claim 8 , wherein a content of the compound represented by the general formula (II) is 0.5% to 3.0% by mass with respect to a total mass of the dye ink composition.

10 . The dye ink composition according to claim 1 , further comprising:

a compound represented by the following general formula (Cy-1),

wherein, in the general formula (Cy-1), 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, and at least one of Z 5 , Z 6 , Z 7 , or Z 8 has a substituent that has an ionic hydrophilic group.

11 . The dye ink composition according to claim 1 , further comprising:

a compound represented by any of the following general formulae (Cy-2) to (Cy-5),

wherein, in the general formulae (Cy-2) to (Cy-5), R 31 , R 32 , R 33 , and R 34 each independently represent a substituted or unsubstituted sulfamoyl group, a substituted or unsubstituted carbamoyl group, a sulfo group, or a carboxy group; in a case where a plurality of R 31 's are present, the plurality of R 31 's may be the same as or different from each other; in a case where a plurality of R 32 's are present, the plurality of R 32 's may be the same as or different from each other; in a case where a plurality of R 33 's are present, the plurality of R 33 's may be the same as or different from each other; in a case where a plurality of R 34 's are present, the plurality of R 34 's may be the same as or different from each other; and o, p, q, and r each independently represent an integer of 1 to 4.

12 . The dye ink composition according to claim 1 , further comprising a chelating agent.

13 . The dye ink composition according to claim 1 , further comprising a preservative.

14 . A cyan dye ink comprising the dye ink composition according to claim 1 .

15 . A dye ink for ink jet recording, the dye ink comprising the dye ink composition according to claim 1 .

16 . An ink jet recording method comprising ejecting the dye ink for ink jet recording according to claim 15 with a recording head for an ink jet process.

17 . An aqueous dye solution comprising:

a preservative;

a compound A represented by the following general formula (I-1);

a compound B represented by the following general formula (I-2);

at least one of a compound C-I represented by the following general formula (I-3-1) or a compound C-II represented by the following general formula (I-3-2); and

a compound D represented by the following general formula (I-4),

wherein, in the aqueous dye solution, in a case where a mass of the compound A is represented by W 1 , a mass of the compound B is represented by W 2 , a sum of a mass of the compound C-I and a mass of the compound C-II is represented by W 3 , a mass of the compound D is represented by W 4 , and a total sum of W 1 , W 2 , W 3 , and W 4 is represented by W A1 ,

a ratio of W 1 to W A1 is 6.0% to 35.0% by mass,

a ratio of W 2 to W A1 is 20.0% to 45.0% by mass,

a ratio of W 3 to W A1 is 15.0% to 45.0% by mass,

a ratio of W 4 to W A1 is 1.0% to 30.0% by mass, and

a ratio of W A1 to a total mass of the aqueous dye solution is 8% to 15% by mass,

wherein, in the general formulae (I-1), (I-2), (I-3-1), (I-3-2), and (I-4), each Z 1 represents an alkyl group, an aryl group, or a heterocyclic group, the alkyl group, the aryl group, and the heterocyclic group having a substituent that has at least one ionic hydrophilic group; a plurality of Z 1 's in the general formulae (I-1), (I-2), (1-3-1), and (I-3-2) may be the same as or different from each other; and

wherein, in the general formulae (I-2), (I-3-1), (I-3-2), and (I-4), each Z 2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; each Z 2 does not have an ionic hydrophilic group; and a plurality of Z 2 's in the general formulae (I-3-1), (I-3-2), and (I-4) may be the same as or different from each other.

18 . The aqueous dye solution according to claim 17 , further comprising a compound E represented by the following general formula (I-5),

wherein, in the aqueous dye solution, in a case where a mass of the compound E is represented by W 5 and a total sum of W 1 , W 2 , W 3 , W 4 , and W 5 is represented by W A2 , a ratio of W A2 to a total mass of the aqueous dye solution is 8% to 15% by mass,

wherein, in the general formula (I-5), each Z 2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; each Z 2 does not have an ionic hydrophilic group; and a plurality of Z 2 's may be the same as or different from each other.

19 . The aqueous dye solution according to claim 17 , further comprising a compound represented by the following general formula (II),

wherein, in the general formula (II), Ar 20 represents a benzene ring or a naphthalene ring; R 21 to R 28 each independently represent a hydrogen atom or a substituent; R 21 and R 22 may be linked to each other to form a ring; R 23 and R 24 may be linked to each other to form a ring; R 25 and R 26 may be linked to each other to form a ring; R 27 and R 28 may be linked to each other to form a ring; R 29 represents a substituent; in a case where Ar 20 represents a benzene ring, k represents an integer of 0 to 4; in a case where Ar 20 represents a naphthalene ring, k represents an integer of 0 to 6; in a case where a plurality of R 29 's are present, the plurality of R 29 's may be the same as or different from each other; and in a case where a plurality of R 29 's are present, the plurality of R 29 's may be linked to each other to form a ring; and at least any one of R 21 to R 29 has a hydrophilic group.

20 . The aqueous dye solution according to claim 17 , further comprising a chelating agent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2022
From: TATEISHI, KEIICHI; SAITOU, TAKASHI; TAKASAKI, YUTA; SAKAI, YUSUKE
To: FUJIFILM CORPORATION
Reel/Frame 059041/0700 →
Priority Claims (2)
JP 2019-153292 · Aug 23, 2019 · national
JP 2020-061656 · Mar 30, 2020 · national
Continuity (2)
Continuation PCTJP2020031689 · Aug 21, 2020
Related Publication 20220169859A1 · Jun 2, 2022
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