Colored dispersion, recording medium, and method for printing hydrophobic fibers

Abstract

Provided are: a colored dispersion containing a dye such as C.I. Disperse Blue 359 and a dye derivative such as C.I. Solvent Blue 105, wherein the content of the dye derivative is less than 10 parts by mass when the total content of the dye and the dye derivative is 100 parts by mass; a recording medium to which the colored dispersion adheres; and a textile printing method for hydrophobic fibers by using the colored dispersion.

Description

[Technical Field]

[0001] The present invention relates to a colored dispersion, a recording medium to which the colored dispersion is attached, and a method for printing hydrophobic fibers using the colored dispersion. [Background technology]

[0002] In recent years, a recording method for plate-less printing using inkjet printing has been proposed, and inkjet printing (inkjet printing) is also being used for printing on fibers, including cloth. Compared to conventional printing methods such as screen printing, inkjet printing has various advantages, including no plate-making required, resource conservation, energy conservation, and ease of high-resolution expression.

[0003] Hydrophobic fibers, such as polyester fibers, are generally dyed with water-insoluble colorants. Therefore, as an aqueous ink for printing hydrophobic fibers by inkjet printing, it is generally necessary to use a dispersion ink with good performance such as dispersion stability, in which a water-insoluble colorant is dispersed in water.

[0004] Inkjet printing methods for hydrophobic fibers can be broadly divided into direct printing and sublimation transfer. Direct printing is a printing method in which ink is applied (printed) directly to hydrophobic fibers, and then the dye in the ink is caused to adhere to the hydrophobic fibers by heat treatment such as high-temperature steaming. On the other hand, sublimation transfer is a printing method in which ink is applied (printed) to an intermediate recording medium (such as dedicated transfer paper), the ink-applied surface of the intermediate recording medium is superimposed on the hydrophobic fibers, and then the dye is transferred from the intermediate recording medium to the hydrophobic fibers by heat.

[0005] The sublimation transfer method is primarily used in the printing of banners and other items, and uses an easily sublimable dye in the ink, which is highly suitable for transfer to hydrophobic fibers through heat treatment. The process involves two steps: (1) printing, in which the dye ink is applied to an intermediate recording medium using an inkjet printer, and (2) transfer, in which the dye is transferred from the intermediate recording medium to the fibers through heat treatment, and then fixed. Since commercially available transfer paper can be widely used, no pretreatment of the fibers is required, and the washing step is also omitted.

[0006] As an ink for a sublimation transfer method, an aqueous ink in which a water-insoluble dye is dispersed in water is generally used. For example, Patent Document 1 describes that an aqueous ink is prepared by adding a water-soluble organic solvent as a humectant (anti-drying agent), a surfactant as a surface tension adjuster, and other additives (pH adjuster, antiseptic / anti-fungal agent, antifoaming agent, etc.) to a dye dispersion in which a water-insoluble dye selected from a disperse dye and an oil-soluble dye is dispersed in water using a dispersant, and optimizing physical properties (physical properties) such as particle size, viscosity, surface tension, and pH. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2005 / 121263 [Patent Document 2] Patent No. 6191234 Summary of the Invention [Problem to be solved by the invention]

[0008] However, the present inventors have studied conventional aqueous inks in which a water-insoluble dye is dispersed in water and have found that even if the dispersion stability of the dye dispersion is relatively good, when a component such as a surfactant is added to the dye dispersion to prepare an aqueous ink, the particles in the aqueous ink aggregate and the dispersion stability decreases.

[0009] An object of the present invention is to provide a colored dispersion liquid that has excellent dispersion stability and in which particle aggregation during storage is suppressed, a recording medium to which the colored dispersion liquid is attached, and a method for printing hydrophobic fibers using the colored dispersion liquid. [Means for solving the problem]

[0010] Specific means for solving the above problems include the following embodiments. 1) (A) a dye which is a compound represented by any one of the following formulas (1a) to (1c) or CI Disperse Blue 360; (B) a dye derivative which is a compound represented by any one of the following formulas (2a), (2b), (2c-1), (2c-2), (2d-1) to (2d-3); and water; The combination of the dye (A) and the dye derivative (B) is selected from the following (a) to (d): (a) a combination of a compound represented by the following formula (1a) and a compound represented by the following formula (2a): (b) a combination of a compound represented by the following formula (1b) and a compound represented by the following formula (2b): (c) a combination of a compound represented by the following formula (1c) and at least one compound selected from a compound represented by the following formula (2c-1) and a compound represented by the following formula (2c-2): (d) A combination of CI Disperse Blue 360 ​​and at least one compound selected from the group consisting of a compound represented by the following formula (2d-1), a compound represented by the following formula (2d-2), and a compound represented by the following formula (2d-3): Either A colored dispersion liquid in which the content of the (B) dye derivative is less than 10 parts by mass when the total content of the (A) dye and the (B) dye derivative is taken as 100 parts by mass. [ka] (In formula (1a), R 1a R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, or a phenyl group which may have a substituent. 2a , R3a Each of X independently represents a hydrogen atom or a cyano group. a is a hydrogen atom, a hydroxyl group, or -NHR 4a R represents a group represented by 4a represents a hydrogen atom or an optionally substituted phenyl group. [ka] (In formula (1b), R 1b , R 2b each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent. [ka] (In formula (1c), R 1c ~R 10c each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, a phenyl group which may have a substituent, or a hydroxy group. [ka] (In formula (2a), R 5a , R 6a R each independently represents an alkyl group having 1 to 6 carbon atoms which may have a substituent. 7a , R 8a each independently represents a hydrogen atom or a halogen atom. [ka] (In formula (2b), A b represents a carbon atom or a nitrogen atom. n represents a value of 0 to 1. R 3b , R 4b R each independently represents an aliphatic group which may have a substituent. 3b , R 4b may be bonded to each other to form a single ring or a condensed ring which may have a substituent. 5b represents an aliphatic group which may have a substituent. 3b , R 4b , R 5bmay be bonded to each other to form a fused ring which may have a substituent. 6b , R 7b R each independently represents a hydrogen atom, a hydroxy group, or a bromine atom. 8b , R 9b R each independently represents an aliphatic group which may have a substituent. 8b , R 9b may be bonded to each other to form a monocyclic or condensed ring which may have a substituent. b , R 3b ~R 9b The combinations that result in a compound represented by the formula (1b) are excluded.) [ka] (In formula (2c-1), R 11c ~R 16c are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a halogen atom, or -NHR 17c or a group represented by -OR 18c R represents a group represented by 17c , R 18c each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. [ka] (In formula (2c-2), R 19c ~R 23c each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a halogen atom, or -OR 24c R represents a group represented by 24c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. [ka] (In formula (2d-1), R 1d , R 2d each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a cyano group, provided that R 1d , R2d Except when R also represents a hydrogen atom. 3d , R 4d each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a halogen atom. [ka] (In formula (2d-2), R 5d , R 6d each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms which may have a substituent. [ka] (In formula (2d-3), R 7d represents a methoxy group or a hydrogen atom. 8d represents a halogen atom or a group represented by -NHCOCH3. 9d , R 10d represents an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a group represented by -C2H4OCOC2H5.

[0011] 2) 1), wherein the content of the (B) dye derivative is 0.1 to 5 parts by mass when the total content of the (A) dye and the (B) dye derivative is 100 parts by mass.

[0012] 3) 1), wherein the content of the (B) specific compound is 0.5 to 5 parts by mass when the total content of the (A) dye and the (B) dye derivative is 100 parts by mass.

[0013] 4) The colored dispersion liquid according to any one of 1) to 3), wherein the compound represented by formula (1a) is CI Disperse Blue 359.

[0014] 5) The colored dispersion liquid according to any one of 1) to 3), wherein the compound represented by formula (1b) is CI Disperse Yellow 54.

[0015] 6) The colored dispersion liquid according to any one of 1) to 3), wherein the compound represented by formula (1c) is CI Solvent Orange 60.

[0016] 7) The colored dispersion liquid according to any one of 1) to 6), further containing a dispersant.

[0017] 8) 7) The colored dispersion according to 7), wherein the dispersant contains a formalin condensate of an aromatic sulfonic acid or a salt thereof.

[0018] 9) 8) The colored dispersion according to 8), wherein the formalin condensate of aromatic sulfonic acid or its salt is a formalin condensate of sodium naphthalenesulfonate or its salt.

[0019] 10) 8) The colored dispersion according to 8), wherein the formalin condensate of aromatic sulfonic acid or its salt is a formalin condensate of creosote oil sulfonic acid or its salt.

[0020] 11) The colored dispersion liquid according to any one of items 7) to 10), wherein the dispersant contains a phytosterol compound.

[0021] 12) 7) The colored dispersion liquid according to 7), wherein the dispersant comprises at least one selected from polyoxyethylene aryl phenyl ether-based dispersants and polyoxyethylene aryl phenyl ether sulfate-based dispersants.

[0022] 13) A recording medium having the colored dispersion liquid according to any one of 1) to 12) attached thereto.

[0023] 14) 13) The recording medium according to 13), which is made of hydrophobic fibers.

[0024] 15) a printing step of depositing droplets of the color dispersion liquid according to any one of 1) to 12) onto an intermediate recording medium to obtain a recorded image; a transfer step of bringing hydrophobic fibers into contact with the surface of the intermediate recording medium to which the color dispersion liquid has been applied and performing a heat treatment to transfer the recorded image to the hydrophobic fibers; A method for printing hydrophobic fibers, comprising: [Effects of the Invention]

[0025] According to the present invention, it is possible to provide a colored dispersion liquid that has excellent dispersion stability and in which particle aggregation during storage is suppressed, a recording medium to which the colored dispersion liquid is attached, and a method for printing hydrophobic fibers using the colored dispersion liquid. DETAILED DESCRIPTION OF THE INVENTION

[0026] <Colored dispersion> The colored dispersion according to this embodiment contains (A) a dye, which is a compound represented by any one of the above formulae (1a) to (1c) or CI Disperse Blue 360; (B) a dye derivative, which is a compound represented by any one of the above formulae (2a), (2b), (2c-1), (2c-2), (2d-1) to (2d-3); and water. "CI" is an abbreviation for Color Index.

[0027] However, the combination of the dye (A) and the dye derivative (B) in the colored dispersion liquid according to this embodiment is any one of the following combinations (a) to (d). (a) A combination of a compound represented by the above formula (1a) and a compound represented by the above formula (2a). (b) A combination of a compound represented by the above formula (1b) and a compound represented by the above formula (2b). (c) A combination of a compound represented by the above formula (1c) and at least one compound selected from a compound represented by the above formula (2c-1) and a compound represented by the above formula (2c-2). (d) A combination of CI Disperse Blue 360 ​​and at least one compound selected from the compounds represented by the above formula (2d-1), the compounds represented by the above formula (2d-2), and the compounds represented by the above formula (2d-3).

[0028] Furthermore, in the colored dispersion liquid according to this embodiment, the content of the (B) dye derivative is less than 10 parts by mass when the total content of the (A) dye and the (B) dye derivative is taken as 100 parts by mass. By setting the content of the (B) dye derivative at the above ratio, it tends to be possible to stably maintain the dispersed state of particles in the colored dispersion liquid. When the total content of the (A) dye and the (B) dye derivative is taken as 100 parts by mass, the content of the (B) dye derivative is preferably 0.1 to 5 parts by mass, more preferably 0.5 to 5 parts by mass.

[0029] [Compound represented by formula (1a)] In the above formula (1a), R 1a R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, or a phenyl group which may have a substituent. 2a , R 3a Each of X independently represents a hydrogen atom or a cyano group. a is a hydrogen atom, a hydroxyl group, or -NHR 4a R represents a group represented by 4a represents a hydrogen atom or an optionally substituted phenyl group.

[0030] Examples of the alkyl group having 1 to 4 carbon atoms include linear alkyl groups such as methyl, ethyl, n-propyl, and n-butyl; and branched alkyl groups such as isopropyl, sec-butyl, and tert-butyl.

[0031] Examples of substituents that the alkyl group having 1 to 4 carbon atoms may have include a hydroxy group, a carboxy group, a sulfo group, a phosphate group, a silanol group, a halogen atom, a cyano group, a nitro group, an amino group, an alkoxy group, an aryloxy group, a silyloxy group, a carbamoyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an alkylcarboxy group, an arylcarboxy group, a heterocyclic group, an aromatic ring group, etc. These substituents may further have any optional substituent.

[0032] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0033] Examples of the amino group include an amino group, a methylamino group, an ethylamino group, an n-butylamino group, a phenylamino group, a dimethylamino group, a diethylamino group, a di-n-butylamino group, a diphenylamino group, a dinaphthylamino group, an ethylmethylamino group, and a methylphenylamino group.

[0034] Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-butoxy group, and a tert-butoxy group.

[0035] Examples of the aryloxy group include a phenoxy group and a naphthoxy group.

[0036] Examples of the silyloxy group include a trimethylsilyloxy group and a tert-butyldimethylsilyloxy group.

[0037] Examples of the alkylcarbonyl group include an acetyl group, an ethylcarbonyl group, and an n-butylcarbonyl group.

[0038] Examples of the arylcarbonyl group include a phenylcarbonyl group, a naphthylcarbonyl group, and a fluorenocarbonyl group.

[0039] Examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group.

[0040] Examples of the alkylcarboxy group include a methylcarboxy group, an ethylcarboxy group, and an n-butylcarboxy group.

[0041] The arylcarboxy group includes, for example, a phenylcarboxy group.

[0042] Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, a thiazole group, and a benzothiazole group.

[0043] Examples of the aromatic ring group include a phenyl group, a naphthyl group, and a fluorenyl group.

[0044] Examples of the substituent that the phenyl group may have include alkyl groups as well as the same substituents as those in the above-mentioned "alkyl group having 1 to 4 carbon atoms which may have a substituent." These substituents may further have an arbitrary substituent.

[0045] When the phenyl group has an alkyl group as a substituent, examples of the alkyl group include alkyl groups having 1 to 8 carbon atoms, such as linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, and n-octyl groups; branched alkyl groups such as isopropyl, sec-butyl, tert-butyl, and neopentyl groups; and cyclic alkyl groups such as cyclopentyl and cyclohexyl groups.

[0046] R in the above formula (1a) 1a is preferably an alkyl group having 1 to 4 carbon atoms which may have a substituent, or a phenyl group which may have a substituent, and more preferably an ethyl group or a phenyl group substituted with a methyl group at the p-position.

[0047] R in the above formula (1a) 2a, R 3a Preferably, both are hydrogen atoms, or one is a cyano group and the other is a hydrogen atom.

[0048] X in the above formula (1a) a As the group, a hydroxy group or -NHR 4a is preferably a hydroxy group or a group represented by -NHR 4a R 4a is preferably a hydrogen atom or a methyl group.

[0049] Among the compounds represented by the above formula (1a), preferred examples include CI Disperse Blue 72, 359; CI Solvent Blue 63; and the like, with CI Disperse Blue 359 being preferred.

[0050] [Compound represented by formula (1b)] In the above formula (1b), R 1b , R 2b each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.

[0051] Examples of the alkyl group having 1 to 20 carbon atoms include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, and an n-octyl group; and branched alkyl groups such as an isopropyl group, a sec-butyl group, a tert-butyl group, and a neopentyl group.

[0052] Examples of the substituent that the alkyl group having 1 to 20 carbon atoms may have include the same groups as the substituents in the above-mentioned "alkyl group having 1 to 4 carbon atoms which may have a substituent."

[0053] R in the above formula (1b) 1b , R 2b are preferably all hydrogen atoms.

[0054] Among the compounds represented by the above formula (1b), preferred examples include CI Disperse Yellow 54.

[0055] [Compound represented by formula (1c)] In the above formula (1c), R 1c ~R 10c each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, a phenyl group which may have a substituent, or a hydroxy group.

[0056] Examples of the halogen atom, the alkyl group having 1 to 4 carbon atoms which may have a substituent, and the phenyl group which may have a substituent include the same groups as those mentioned above.

[0057] R in the above formula (1c) 1c ~R 10c are each preferably independently a hydrogen atom or a halogen atom.

[0058] Among the compounds represented by the above formula (1c), preferred examples include CI Solvent Orange 60; CI Solvent Red 135, 176; and the like, with CI Solvent Orange 60 being preferred.

[0059] [Compound represented by formula (2a)] In the above formula (2a), R 5a , R 6a R each independently represents an alkyl group having 1 to 6 carbon atoms which may have a substituent. 7a , R 8a each independently represents a hydrogen atom or a halogen atom.

[0060] Examples of the alkyl group having 1 to 6 carbon atoms include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl groups; branched alkyl groups such as isopropyl, sec-butyl, and tert-butyl groups; and cyclic alkyl groups such as cyclopentyl and cyclohexyl groups.

[0061] Examples of the substituent that the alkyl group having 1 to 6 carbon atoms may have include the same groups as the substituents in the above-mentioned "alkyl group having 1 to 4 carbon atoms which may have a substituent."

[0062] The halogen atom may be the same as above.

[0063] R in the above formula (2a) 5a , R 6a is preferably each independently an alkyl group having 1 to 6 carbon atoms, more preferably each independently a methyl group, an ethyl group, an n-butyl group, or an isopropyl group, and even more preferably both are a methyl group, an ethyl group, an n-butyl group, or an isopropyl group, or one is a methyl group and the other is an isopropyl group.

[0064] R in the above formula (2a) 7a , R 8a are each preferably independently a hydrogen atom or a chlorine atom, and more preferably both are hydrogen atoms or both are chlorine atoms.

[0065] Among the compounds represented by the above formula (2a), preferred examples include CI Solvent Blue 35, 36, 78, 102, 105, 112, and the like.

[0066] [Compound represented by formula (2b)] In the above formula (2b), A b represents a carbon atom or a nitrogen atom. n represents a value of 0 to 1. R 3b , R 4b R each independently represents an aliphatic group which may have a substituent. 3b , R 4b may be bonded to each other to form a single ring or a condensed ring which may have a substituent. 5b represents an aliphatic group which may have a substituent. 3b , R 4b , R 5bmay be bonded to each other to form a fused ring which may have a substituent. 6b , R 7b R each independently represents a hydrogen atom, a hydroxy group, or a bromine atom. 8b , R 9b R each independently represents an aliphatic group which may have a substituent. 8b , R 9b may be bonded to each other to form a monocyclic or condensed ring which may have a substituent. b , R 3b ~R 9b The combinations that result in the compound represented by the above formula (1b) are excluded.

[0067] Examples of the aliphatic group include the above-mentioned "optionally substituted alkyl group having 1 to 20 carbon atoms" as well as alkenyl groups and alkynyl groups.

[0068] Examples of the substituent that the aliphatic group may have include the same as the substituents in the above-mentioned "alkyl group having 1 to 4 carbon atoms which may have a substituent."

[0069] Examples of the monocyclic ring which may have a substituent include a benzene ring, a pyridine ring, a cyclohexane ring, and a quinone ring.

[0070] Examples of the fused ring which may have a substituent include a naphthalene ring, an anthracene ring, a benzothiazole ring, a naphthothiazole ring, etc. When an isomer exists in the fused ring, any isomer may be used, or a plurality of isomers may be mixed.

[0071] A in the above formula (2b) b is preferably a nitrogen atom.

[0072] R in the above formula (2b) 3b , R 4bare preferably bonded to each other to form a monocyclic or condensed ring which may have a substituent, more preferably to form a benzene ring which may have a substituent. Preferred substituents are halogen atoms, aromatic ring groups, and alkoxycarbonyl groups.

[0073] When n is 1, R in the above formula (2b) 5b is preferably an aliphatic group, and R 3b , R 4b , R 5b are more preferably bonded to each other to form a fused ring which may have a substituent.

[0074] R in the above formula (2b) 6b , R 7b Preferably, each of the groups is a hydrogen atom, one is a hydroxy group and the other is a hydrogen atom, or one is a hydroxy group and the other is a bromine atom.

[0075] R in the above formula (2b) 8b , R 9b are preferably bonded to each other to form a monocyclic or condensed ring which may have a substituent, more preferably to form a benzene ring which may have a substituent. Preferred substituents are alkyl groups having 1 to 20 carbon atoms, halogen atoms, aromatic ring groups, and alkoxycarbonyl groups.

[0076] In the above formula (2b), n and A b , R 3b ~R 9b A preferred combination is, for example, b is a nitrogen atom, and R 3b and R 4b and R are bonded to each other to form a benzene ring which may have a substituent; 6b is a hydroxy group, and R 8b and R 9b and R are bonded to each other to form a benzene ring which may have a substituent, and 7b , R 3b and R 4band R 8b and R 9b and are bonded to each other to form a benzene ring, and one to three of the substituents are each independently an atom or group selected from the group consisting of a bromine atom, a phenyl group, and an alkoxycarbonyl group.

[0077] Preferable examples of the compounds represented by the formula (2b) include CI Disperse Yellow 64, 134, 143, 149, and 160. CI Disperse Yellow 134 is represented by the following formula.

[0078] [ka]

[0079] [Compound represented by formula (2c-1)] In the above formula (2c-1), R 11c ~R 16c are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a halogen atom, or -NHR 17c or a group represented by -OR 18c R represents a group represented by 17c , R 18c each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

[0080] Examples of the alkyl group having 1 to 6 carbon atoms and the halogen atom which may have a substituent include the same groups as those mentioned above.

[0081] R in the above formula (2c-1) 11c ~R 16c are each independently a hydrogen atom, -NHR 17c or a group represented by -OR 18c In this case, R 17c is preferably a methyl group or a hydroxyethyl group, and R 18cis preferably a methyl group.

[0082] Among the compounds represented by the above formula (2c-1), preferred examples include CI Solvent Red 179, 180; CI Solvent Orange 79; CI Solvent Yellow 119; and the like.

[0083] [Compound represented by formula (2c-2)] In the above formula (2c-2), R 19c ~R 23c each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a halogen atom, or -OR 24c R represents a group represented by 24c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

[0084] Examples of the alkyl group having 1 to 6 carbon atoms and the halogen atom which may have a substituent include the same groups as those mentioned above.

[0085] R in the above formula (2c-2) 19c ~R 23c are preferably all hydrogen atoms.

[0086] Among the compounds represented by the above formula (2c-2), preferred examples include CI Disperse Orange 118.

[0087] [Compound represented by formula (2d-1)] In the above formula (2d-1), R 1d , R 2d each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a cyano group, provided that R 1d , R 2d Except when R also represents a hydrogen atom. 3d , R 4d each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a halogen atom.

[0088] Examples of the alkyl group having 1 to 2 carbon atoms include a methyl group and an ethyl group. Examples of the substituent that the alkyl group having 1 to 2 carbon atoms may have include the same groups as the substituents in the above-mentioned "alkyl group having 1 to 4 carbon atoms which may have a substituent."

[0089] The halogen atom may be the same as above.

[0090] Of the compounds represented by the above formula (2d-1), preferred are, for example, compounds represented by the following formulae (2d-1-1) to (2d-1-3).

[0091] [ka]

[0092] [Compound represented by formula (2d-2)] In the above formula (2d-2), R 5d , R 6d each independently represents a hydrogen atom or an optionally substituted alkyl group having 1 to 2 carbon atoms. Examples of the optionally substituted alkyl group having 1 to 2 carbon atoms include the same groups as those mentioned above.

[0093] Among the compounds represented by the above formula (2d-2), preferred are, for example, compounds represented by the following formulae (2d-2-1) to (2d-2-4).

[0094] [ka]

[0095] [Compound represented by formula (2d-3)] In the above formula (2d-3), R 7d represents a methoxy group or a hydrogen atom. 8d represents a halogen atom or a group represented by -NHCOCH3. 9d , R 10drepresents an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a group represented by -C2H4OCOC2H5. Examples of the alkyl group having 1 to 2 carbon atoms which may have a substituent include the same groups as those mentioned above.

[0096] Among the compounds represented by the above formula (2d-3), preferred are, for example, compounds represented by the following formulae (2d-3-1) to (2d-3-4).

[0097] [ka]

[0098] The total content of the (A) dye and the (B) dye derivative is preferably 10 to 25% by mass, and more preferably 14 to 17% by mass, based on the total amount of the colored dispersion.

[0099] [Other colorants] The colored dispersion according to this embodiment may further contain other colorants in addition to the above-described (A) dye and (B) dye derivative, but it is preferred that the content of the (A) dye be the highest among the (A) dye, the (B) dye derivative, and the other colorants in the colored dispersion.

[0100] Examples of other colorants include pigments, disperse dyes, oil-soluble dyes, acid dyes, reactive dyes, and direct dyes, with disperse dyes and oil-soluble dyes being preferred, and disperse dyes being more preferred.

[0101] For example, when the (A) dye and the (B) dye derivative are combined as described above in (a) or (d), examples of the disperse dye include CI Disperse Blue dyes other than the (A) dye and the (B) dye derivative. When the (A) dye and the (B) dye derivative are combined as described above in (b), examples of the disperse dye include CI Disperse Yellow dyes other than the (A) dye and the (B) dye derivative. When the (A) dye and the (B) dye derivative are combined as described above in (c), examples of the disperse dye include CI Disperse Orange dyes other than the (A) dye and the (B) dye derivative.

[0102] The content of the other colorants is preferably 10% by mass or less, and more preferably 6% by mass or less, based on the total amount of the color dispersion.

[0103] [water] The water is preferably ion-exchanged water, distilled water, or other water with few impurities. Sterilized water may also be used.

[0104] The content of water in the color dispersion is appropriately selected depending on the application. The content of water in the color dispersion is usually 200 to 8500 parts by mass per 100 parts by mass of the total of (A) colorant, (B) colorant derivative, and other colorants that may be optionally contained.

[0105] [Dispersant] The color dispersion according to this embodiment preferably further contains a dispersant.

[0106] The dispersant preferably contains, for example, a formalin condensate of an aromatic sulfonic acid or a salt thereof. The formalin condensate of an aromatic sulfonic acid or a salt thereof is an anionic surfactant obtained by a condensation reaction between an aromatic sulfonic acid and formalin.

[0107] Examples of formalin condensates of aromatic sulfonic acids or their salts include formalin condensates of creosote oil sulfonic acid, cresol sulfonic acid, phenol sulfonic acid, naphthalene sulfonic acid, β-naphthol sulfonic acid, β-naphthalene sulfonic acid with β-naphthol sulfonic acid, benzene sulfonic acid, cresol sulfonic acid, 2-naphthol-6-sulfonic acid, lignin sulfonic acid, and the like, or their salts (sodium salt, potassium salt, lithium salt, etc.). Among these, formalin condensates of creosote oil sulfonic acid, naphthalene sulfonic acid, lignin sulfonic acid, and methylnaphthalene sulfonic acid or their salts are preferred. Examples of naphthalene sulfonic acids include α-naphthalene sulfonic acid and β-naphthalene sulfonic acid, with β-naphthalene sulfonic acid being preferred.

[0108] Formalin condensates of aromatic sulfonic acids or salts thereof can also be obtained as commercially available products. For example, formalin condensates of β-naphthalenesulfonic acid or salts thereof include Demol N (manufactured by Kao Corporation). Formalin condensates of creosote oil sulfonic acid or salts thereof include Demol C (manufactured by Kao Corporation) and Labelin W series (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). Formalin condensates of special aromatic sulfonic acids or salts thereof include Demol SN-B (manufactured by Kao Corporation). Formalin condensates of methylnaphthalenesulfonic acid or salts thereof include Labelin AN series (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). Of these, Demol N, Labelin AN series, and Labelin W series are preferred, Demol N and Labelin W series are more preferred, and Labelin W series is even more preferred. Examples of lignin sulfonic acid include Vanilex N, Vanilex RN, Vanilex G, and Pearlex DP (all manufactured by Nippon Paper Industries Co., Ltd.). Of these, Vanilex RN, Vanilex N, and Vanilex G are preferred.

[0109] Examples of dispersants other than the formalin condensate of aromatic sulfonic acid or its salt include known dispersants, surfactants, resin dispersants, etc. In addition, the terms dispersant and surfactant may refer to the same substance. Types of dispersants include anionic dispersants, nonionic dispersants, cationic dispersants, amphoteric dispersants, etc. Among these, at least one dispersant selected from anionic dispersants and nonionic dispersants is preferred.

[0110] Examples of the anionic dispersant other than the formalin condensate of aromatic sulfonic acid or its salt include polymeric sulfonic acid, lignosulfonic acid, formalin condensate of lignosulfonic acid or their salts.

[0111] Examples of nonionic dispersants include alkylene oxide adducts of phytosterols, alkylene oxide adducts of cholestanols, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene alkylamines, glycerin fatty acid esters, oxyethyleneoxypropylene block polymers, and substituted derivatives thereof. Among these, alkylene oxide adducts of phytosterols (also called phytosterol compounds) and alkylene oxide adducts of cholestanols (also called cholestanol compounds) are preferred, and phytosterol compounds are more preferred.

[0112] As the alkylene oxide adduct of phytosterols, C2-C4 alkylene oxide adducts of phytosterols are preferred, and ethylene oxide adducts are more preferred. In this specification, the term "phytosterols" is used to mean both "phytosterol" and "hydrogenated phytosterol." For example, ethylene oxide adducts of phytosterols include ethylene oxide adducts of phytosterol and ethylene oxide adducts of hydrogenated phytosterol.

[0113] As the alkylene oxide adduct of cholestanols, C2-C4 alkylene oxide adducts of cholestanols are preferred, and ethylene oxide adducts are more preferred. In this specification, "cholestanols" is used to mean both "cholestanol" and "hydrogenated cholestanol". For example, ethylene oxide adducts of cholestanols include ethylene oxide adducts of cholestanol and ethylene oxide adducts of hydrogenated cholestanol.

[0114] The amount of alkylene oxide (preferably C2-C4 alkylene oxide, more preferably ethylene oxide) added per mole of phytosterols or cholestanols is preferably about 10-50 moles, and the HLB is preferably about 13-20.

[0115] Commercially available alkylene oxide adducts of phytosterols include NIKKOL BPS-20 and NIKKOL BPS-30 (both manufactured by Nikko Chemicals Co., Ltd., ethylene oxide adducts of phytosterols), and NIKKOL BPSH-25 (also manufactured by Nikko Chemicals Co., Ltd., ethylene oxide adducts of hydrogenated phytosterols).Commercially available alkylene oxide adducts of cholestanols include NIKKOL DHC-30 (manufactured by Nikko Chemicals Co., Ltd., ethylene oxide adducts of cholestanol).

[0116] Examples of resin dispersants include styrene-(meth)acrylic copolymers. The styrene-(meth)acrylic copolymer is a copolymer of a styrene-based monomer and a (meth)acrylic monomer. Specific examples of copolymers include (α-methyl)styrene-acrylic acid copolymer, (α-methyl)styrene-acrylic acid-acrylic acid ester copolymer, (α-methyl)styrene-methacrylic acid copolymer, (α-methyl)styrene-methacrylic acid-acrylic acid ester copolymer, (α-methyl)styrene-acrylic acid ester-maleic anhydride copolymer, acrylic acid ester-styrene sulfonic acid copolymer, and (α-methyl)styrene-methacrylic sulfonic acid copolymer. In this specification, "(meth)acrylic" is used to include both "acrylic" and "methacrylic." Furthermore, "(α-methyl)styrene" is used to include both "α-methylstyrene" and "styrene."

[0117] The mass average molecular weight of the styrene-(meth)acrylic copolymer is, for example, preferably from 1,000 to 20,000, more preferably from 2,000 to 19,000, and even more preferably from 5,000 to 17,000. The mass average molecular weight of the styrene-(meth)acrylic copolymer can be measured by GPC (gel permeation chromatography).

[0118] The acid value of the styrene-(meth)acrylic copolymer is, for example, preferably 50 to 250 mgKOH / g, more preferably 100 to 250 mgKOH / g, and even more preferably 150 to 250 mgKOH / g. By setting the acid value to 50 mgKOH / g or more, the solubility in water and dispersion stabilization ability tend to be improved. Furthermore, by setting the acid value to 250 mgKOH / g or less, bleeding of printed images due to increased affinity with aqueous media tends to be suppressed. The acid value of a resin represents the number of mg of KOH required to neutralize 1 g of resin, and can be measured according to JIS-K3054.

[0119] The glass transition temperature of the styrene-(meth)acrylic copolymer is, for example, preferably 45 to 135°C, more preferably 55 to 120°C, and even more preferably 60 to 110°C.

[0120] Commercially available styrene-(meth)acrylic copolymers include, for example, Joncryl RTM 67, 678, 680, 682, 683, 690, 52J, 57J, 60J, 63J, 70J, JDX-6180, HPD-196, HPD96J, PDX-6137A, 6610, JDX-6500, JDX-6639, PDX-6102B, PDX-6124 (all manufactured by BASF), etc. In this specification, the superscript RTM means a registered trademark. Among these, Joncryl 67 (mass average molecular weight: 12,500, acid value: 213 mg KOH / g), 678 (mass average molecular weight: 8,500, acid value: 215 mg KOH / g), 682 (mass average molecular weight: 1,700, acid value: 230 mg KOH / g), 683 (mass average molecular weight: 4,900, acid value: 215 mg KOH / g), 690 (mass average molecular weight: 16,500, acid value: 240 mg KOH / g), etc. are preferred, and Joncryl 678 is more preferred.

[0121] It is also a preferred embodiment to use a polyoxyethylene aryl phenyl ether-based dispersant or a polyoxyethylene aryl phenyl ether sulfate-based dispersant as the dispersant.

[0122] Examples of polyoxyethylene arylphenyl ether-based dispersants include styrylphenol compounds such as polyoxyethylene monostyrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, and polyoxyethylene tetrastyrylphenyl ether; benzylphenol compounds such as polyoxyethylene monobenzylphenyl ether, polyoxyethylene dibenzylphenyl ether, and polyoxyethylene tribenzylphenyl ether; cumylphenol compounds such as polyoxyethylene cumylphenyl ether; polyoxyethylene naphthylphenyl ether, polyoxyethylene biphenyl ether, and polyoxyethylene phenoxyphenyl ether. Among these, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, polyoxyethylene dibenzylphenyl ether, polyoxyethylene tribenzylphenyl ether, and polyoxyethylene cumylphenyl ether are preferred.

[0123] The number of repeating polyoxyethylene groups in the polyoxyethylene arylphenyl ether is preferably 1 to 30, and more preferably 15 to 30. When the number of repeating polyoxyethylene groups is 1 or more, the compatibility with aqueous solvents and the like tends to be excellent. When the number of repeating polyoxyethylene groups is 30 or less, the viscosity tends not to be too high.

[0124] Commercially available styrylphenol compounds include, for example, the Noigen EA series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.); Paionin D-6112, Paionin D-6115, Paionin D-6120, Paionin D-6131, Paionin D-6512, Takesurf D-6413, DTD-51, Paionin D-6112, and Paionin D-6320 (all manufactured by Takemoto Yushi Co., Ltd.); TS-1500, TS-2000, TS-2600, and SM-174N (all manufactured by Toho Chemical Industry Co., Ltd.); and Emulgen A60, Emulgen A90, and Emulgen A500 (all manufactured by Kao Corporation). Commercially available benzylphenol compounds include, for example, Emulgen B-66 (manufactured by Kao Corporation). Commercially available cumylphenol compounds include, for example, Newcol CMP series (manufactured by Nippon Nyukazai Co., Ltd.).

[0125] Examples of polyoxyethylene aryl phenyl ether sulfates include the sulfates of the above-mentioned polyoxyethylene aryl phenyl ethers.

[0126] Commercially available polyoxyethylene arylphenyl ether sulfate dispersants include, for example, SM-57, SM-130, and SM-210 (all manufactured by Toho Chemical Industry Co., Ltd.).

[0127] The above dispersants may be used alone or in combination of two or more.

[0128] The content of the dispersant is preferably 1 to 200 parts by mass, and more preferably 7 to 140 parts by mass, relative to 100 parts by mass of the total of (A) dye, (B) dye derivative, and other colorants that may be optionally contained.

[0129] [Additives] The color dispersion liquid according to this embodiment may contain additives other than those described above. Examples of additives include water-soluble organic solvents, preservatives, surfactants, pH adjusters, chelating agents, rust inhibitors, water-soluble UV absorbers, water-soluble polymer compounds, viscosity adjusters, dye dissolving agents, antioxidants, and resin emulsions. Among these, it is preferable to contain at least one selected from the group consisting of water-soluble organic solvents, preservatives, surfactants, and pH adjusters.

[0130] The content of the water-soluble organic solvent is preferably 5 to 50% by mass, and more preferably 10 to 40% by mass, based on the total amount of the color dispersion. The content of other additives is preferably 0.1 to 5% by mass, and more preferably 0.2 to 2% by mass, based on the total amount of the color dispersion.

[0131] Examples of water-soluble organic solvents include glycol-based solvents, polyhydric alcohols, and pyrrolidones. Examples of glycol-based solvents include glycerin, polyglycerin (#310, #750, #800), diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, undecaglycerin, dodecaglycerin, tridecaglycerin, and tetradecaglycerin. Examples of polyhydric alcohols include C2-C6 polyhydric alcohols having 2 to 3 alcoholic hydroxyl groups; di- or tri-C2-C3 alkylene glycols; poly-C2-C3 alkylene glycols having 4 or more repeating units and a molecular weight of about 20,000 or less, preferably liquid polyalkylene glycols; and the like. Specific examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, 1,3-propanediol, 1,2-butanediol, thiodiglycol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 3-methyl-1,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, glycerin, trimethylolpropane, 1,3-pentanediol, and 1,5-pentanediol. Pyrrolidones include 2-pyrrolidone and N-methyl-2-pyrrolidone. For convenience, compounds that dissolve in water and act as wetting agents are also included in the term "water-soluble organic solvent." Examples of such compounds include urea, ethylene urea, and sugars.

[0132] Considering the storage stability of the colored dispersion liquid according to this embodiment, the water-soluble organic solvent is preferably a solvent in which the colorant has a low solubility, and it is particularly preferable to use glycerin in combination with a solvent other than glycerin (preferably a polyhydric alcohol other than glycerin).

[0133] Examples of preservatives include organic sulfur compounds, organic nitrogen sulfur compounds, organic halogen compounds, haloaryl sulfone compounds, iodopropargyl compounds, N-haloalkylthio compounds, nitrile compounds, pyridine compounds, 8-oxyquinolines, benzothiazole compounds, isothiazolinone compounds, dithiols, pyridine oxide compounds, nitropropane compounds, organic tin compounds, phenol compounds, quaternary ammonium salt compounds, triazine compounds, thiazine compounds, anilides, adamantane compounds, dithiocarbamates, brominated indanone compounds, benzyl bromoacetate compounds, and inorganic salt compounds. Specific examples of organic halogen compounds include sodium pentachlorophenol. Specific examples of pyridine oxide compounds include sodium 2-pyridinethiol-1-oxide. Specific examples of isothiazoline compounds include 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride, etc. Specific examples of other antiseptics and fungicides include anhydrous sodium acetate, sodium sorbate, sodium benzoate, and Proxel (trade name) manufactured by Lonza. RTM GXL(S), Proxel RTM Examples include XL-2(S).

[0134] Examples of the surfactant include known surfactants such as anionic, cationic, amphoteric, nonionic, silicone, and fluorine-based surfactants.

[0135] Examples of anionic surfactants include alkyl sulfonates, alkyl carboxylates, α-olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acylamino acids and their salts, N-acylmethyltaurines, alkyl sulfates, polyoxyalkyl ether sulfates, alkyl sulfates, polyoxyethylene alkyl ether phosphates, rosin acid soaps, castor oil sulfates, lauryl alcohol sulfates, alkylphenol phosphates, alkyl phosphates, alkylaryl sulfonates, diethyl sulfosuccinates, diethylhexyl sulfosuccinates, dioctyl sulfosuccinates, etc. Specific examples of commercially available products include Hitenol LA-10, LA-12, LA-16, Neohitenol ECL-30S, and ECL-45, all manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.

[0136] Examples of cationic surfactants include 2-vinylpyridine derivatives and poly(4-vinylpyridine) derivatives.

[0137] Examples of amphoteric surfactants include lauryl dimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, coconut oil fatty acid amidopropyl dimethylaminoacetic acid betaine, polyoctyl polyaminoethyl glycine, and imidazoline derivatives.

[0138] Examples of nonionic surfactants include ether-based surfactants such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, and polyoxyethylene alkyl ether; ester-based surfactants such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, and polyoxyethylene stearate; acetylene glycol (alcohol)-based surfactants such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, and 3,5-dimethyl-1-hexyn-3-ol; trade names Surfynol 104, 105, 82, and 465, and Olfin STG, manufactured by Air Products Japan Co., Ltd.; and polyglycol ether-based surfactants (for example, Tergitol, manufactured by SIGMA-ALDRICH). 15-S-7, etc.);

[0139] Examples of silicone surfactants include polyether-modified siloxane, polyether-modified polydimethylsiloxane, etc. Specific examples of commercially available products include BYK-347 (polyether-modified siloxane), BYK-345, and BYK-348 (polyether-modified polydimethylsiloxane), all manufactured by BYK-Chemie.

[0140] Examples of fluorine-based surfactants include perfluoroalkyl sulfonic acid compounds, perfluoroalkyl carboxylic acid compounds, perfluoroalkyl phosphate ester compounds, perfluoroalkyl ethylene oxide adducts, polyoxyalkylene ether polymer compounds having perfluoroalkyl ether groups on the side chains, etc. Specific examples of commercially available products include Zonyl TBS, FSP, FSA, FSN-100, FSN, FSO-100, FSO, FS-300, Capstone FS-30, FS-31 (all manufactured by DuPont); PF-151N, PF-154N (all manufactured by Omnova); etc.

[0141] Any substance can be used as the pH adjuster as long as it does not adversely affect the colored dispersion to be prepared and can control the pH of the colored dispersion to a range of approximately 5 to 11. Specific examples include alkanolamines such as diethanolamine, triethanolamine, and N-methyldiethanolamine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; ammonium hydroxide (aqueous ammonia); alkali metal carbonates such as lithium carbonate, sodium carbonate, sodium bicarbonate, and potassium carbonate; alkali metal salts of organic acids such as potassium acetate; and inorganic bases such as sodium silicate and disodium phosphate, with triethanolamine being preferred.

[0142] Specific examples of the chelating agent include sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium uracildiacetate.

[0143] Examples of the rust inhibitor include acid sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, and dicyclohexylammonium nitrite.

[0144] Examples of water-soluble ultraviolet absorbers include sulfonated benzophenone compounds, benzotriazole compounds, salicylic acid compounds, cinnamic acid compounds, and triazine compounds.

[0145] Examples of the water-soluble polymer compound include polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.

[0146] Examples of viscosity modifiers include water-soluble organic solvents and water-soluble polymer compounds, such as polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.

[0147] Examples of the dye dissolving agent include urea, ε-caprolactam, and ethylene carbonate.

[0148] As the antioxidant, for example, various organic and metal complex anti-fading agents can be used, examples of which include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, and heterocycles.

[0149] Examples of resin emulsions include emulsions formed from acrylic resins, epoxy resins, urethane resins, polyether resins, polyamide resins, unsaturated polyester resins, phenolic resins, silicone resins, fluororesins, polyvinyl resins (vinyl chloride, vinyl acetate, polyvinyl alcohol, etc.), alkyd resins, polyester resins, and amino materials (melamine resins, urea resins, urea resins, melamine formaldehyde resins, etc.). Resin emulsions may contain two or more resins. Two or more resins may form a core / shell structure. Among resin emulsions, urethane resin emulsions are preferred.

[0150] Urethane resin emulsions are commercially available, and many of them are emulsions with a solids concentration of 30 to 60% by mass. Examples of commercially available urethane resin emulsions include Permarin UA-150, 200, 310, 368, 3945, and U-coat UX-320 (all manufactured by Sanyo Chemical Industry Co., Ltd.); Hydran WLS-201, 210, and HW-312B latex (all manufactured by DIC Corporation); and Superflex 150, 170, and 470 (all manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.). Among these, examples of polycarbonate-based urethane resins include Permarin UA-310, 3945, and U-coat UX-320. Among these, examples of polyether-based urethane resins include Permarin UA-150 and 200; U-coat UX-340; and the like.

[0151] The urethane resin in the urethane resin emulsion has an SP value of 8 to 24 (cal / cm 3 ) 1 / 2 It is preferable that the temperature is 8 to 17 (cal / cm 3 ) 1 / 2 More preferably, it is 8 to 11 (cal / cm 3 ) 1 / 2 It is more preferable that the SP value of the urethane resin is calculated by the Fedors method. When the urethane resin has acidic groups and the acidic groups are neutralized to prepare the emulsion, the SP value of the urethane resin before neutralization is used.

[0152] When the urethane resin in the urethane resin emulsion has acidic groups such as carboxyl groups, sulfo groups, or hydroxyl groups, the acidic groups may be converted into alkali salts. For example, the acidic groups can be converted into alkali salts by adding the urethane resin having acidic groups to water and stirring to prepare an aqueous solution, and then adding an alkaline compound to adjust the pH to 6.0 to 12.0. Examples of alkaline compounds include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; and alkaline earth metal hydroxides such as beryllium hydroxide, magnesium hydroxide, calcium hydroxide, and strontium hydroxide. One type of alkaline compound may be used alone, or two or more types may be used in combination.

[0153] [Preparation method of color dispersion liquid, etc.] A method for preparing the colored dispersion liquid according to this embodiment includes, for example, preparing an aqueous dispersion liquid containing (A) the dye, (B) the dye derivative, and a dispersant, and, if necessary, further adding an additive such as a water-soluble organic solvent.

[0154] Methods for preparing an aqueous dispersion include known methods such as stirring and mixing the components constituting the aqueous dispersion using a sand mill (bead mill), roll mill, ball mill, paint shaker, ultrasonic disperser, high-pressure emulsifier, etc. For example, when using a sand mill, first, the components and beads serving as a dispersion medium are charged into the sand mill. Examples of beads that can be used include glass beads, zirconia beads, etc., with a particle diameter of 0.01 to 1 mm. The amount of beads used is preferably 2 to 6 parts by mass per 1 part by mass of the material to be dispersed. Next, the sand mill is operated to perform a dispersion treatment. The dispersion treatment conditions are preferably approximately 1000 to 2000 rpm for 1 to 20 hours. After the dispersion treatment, the beads are removed by filtration or the like to obtain an aqueous dispersion.

[0155] The prepared colored dispersion may be subjected to microfiltration using a membrane filter or the like. In particular, when the colored dispersion is used as an inkjet printing ink, it is preferable to perform microfiltration to prevent nozzle clogging, etc. The pore size of the filter used for microfiltration is usually 0.1 to 1 μm, and preferably 0.1 to 0.8 μm.

[0156] From the viewpoint of high-speed ejection response, the viscosity of the colored dispersion liquid according to this embodiment at 25°C is preferably about 3 to 20 mPa·s when measured with an E-type viscometer. Furthermore, the surface tension of the colored dispersion liquid according to this embodiment at 25°C is preferably about 20 to 45 mN / m when measured with a plate method. In practice, the viscosity is adjusted to obtain appropriate physical property values, taking into consideration the ejection volume, response speed, and ink droplet flight characteristics of the inkjet printer used.

[0157] The color dispersion liquid according to this embodiment can be used in various fields and is suitable for water-based writing inks, water-based printing inks, information recording inks, textile printing, etc. The color dispersion liquid according to this embodiment is particularly preferably used as an inkjet textile printing ink.

[0158] The color dispersion liquid according to this embodiment is unlikely to undergo solid precipitation, changes in physical properties, or changes in color after long-term storage, and has excellent storage stability. It also has good initial filling properties for inkjet printer heads and good continuous printing stability. Furthermore, there is almost no bleeding of the image on the recording medium after printing, making it possible to obtain a clear image.

[0159] The colored dispersion liquid according to this embodiment can also be used as a colored dispersion liquid set in combination with other colored dispersion liquids having different color tones.

[0160] <Recording media> The recording medium according to this embodiment is one to which the colored dispersion liquid according to this embodiment described above is attached. The recording medium is not particularly limited as long as it can be recorded using the colored dispersion liquid according to this embodiment, and examples thereof include fibers, paper (plain paper, inkjet paper, etc.), etc. In particular, the recording medium according to this embodiment is preferably a hydrophobic fiber to which the colored dispersion liquid according to this embodiment is attached.

[0161] Examples of hydrophobic fibers include polyester fibers, nylon fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended fibers using two or more of these fibers. Blended fibers of these hydrophobic fibers with regenerated fibers such as rayon, and natural fibers such as cotton, silk, and wool are also included in the hydrophobic fiber category in this specification. Some of these fibers are known to have an ink-receiving layer (bleed-preventing layer), and such fibers are also included in the hydrophobic fiber category. Methods for forming an ink-receiving layer are well-known, and fibers with ink-receiving layers are commercially available. The material and structure of the ink-receiving layer are not particularly limited, and can be appropriately selected depending on the purpose.

[0162] <Printing method for hydrophobic fibers> The hydrophobic fiber printing method according to this embodiment is a method of printing hydrophobic fibers using the color dispersion liquid according to this embodiment described above. The hydrophobic fiber printing method is broadly divided into a direct printing method and a sublimation transfer method.

[0163] The direct printing method includes a printing step in which droplets of a colored dispersion are deposited on a hydrophobic fiber using an inkjet printer to obtain a recorded image such as a letter or a picture; a fixing step in which the dye in the colored dispersion that has been deposited on the hydrophobic fiber in the printing step is fixed to the hydrophobic fiber by heat; and a washing step in which unfixed dye remaining in the hydrophobic fiber is washed away.

[0164] The fixing step is generally carried out by known steaming or baking. Steaming, for example, involves treating the hydrophobic fibers with a high-temperature steamer at typically 170 to 180°C for about 10 minutes, or with a high-pressure steamer at typically 120 to 130°C for about 20 minutes, thereby fixing the dye to the hydrophobic fibers (also called wet heat fixing). Baking (thermosol), for example, involves treating the hydrophobic fibers at typically 190 to 210°C for about 6 to 120 seconds, thereby fixing the dye to the hydrophobic fibers (also called dry heat fixing).

[0165] The washing step is a step in which the obtained fibers are washed with warm water and, if necessary, with water. The warm water or water used for washing may contain a surfactant. After washing, the hydrophobic fibers are preferably dried, usually at 50 to 120°C for 5 to 30 minutes.

[0166] On the other hand, the sublimation transfer method includes a printing step in which droplets of a colored dispersion are deposited on an intermediate recording medium using an inkjet printer to obtain a recorded image such as letters or a picture, and a transfer step in which hydrophobic fibers are brought into contact with the surface of the intermediate recording medium on which the colored dispersion has been deposited, and the resulting image is transferred to the hydrophobic fibers by heat treatment.

[0167] The intermediate recording medium is preferably one that does not cause the dye in the adhered color dispersion to aggregate on its surface and does not interfere with the sublimation of the dye when the recorded image is transferred to the hydrophobic fiber. An example of such an intermediate recording medium is paper having an ink-receiving layer formed on its surface with inorganic fine particles such as silica, and dedicated paper for inkjet printing can be used.

[0168] The heat treatment in the transfer step is typically a dry heat treatment at about 190 to 200°C.

[0169] The hydrophobic fiber printing method according to this embodiment may further include a pretreatment step of the hydrophobic fiber for the purpose of preventing bleeding, etc. This pretreatment step may include a step of applying an aqueous solution (pretreatment liquid) containing a sizing agent, an alkaline substance, an anti-reducing agent, and a hydrotropic agent to the hydrophobic fiber before the coloring dispersion liquid is applied thereto.

[0170] Examples of adhesives include natural gums such as guar and locust bean; starches; seaweeds such as sodium alginate and funori; plant skins such as pectic acid; cellulose derivatives such as methylcellulose, ethylcellulose, hydroxyethylcellulose, and carboxymethylcellulose; processed starches such as carboxymethyl starch; and synthetic glues such as polyvinyl alcohol and polyacrylic esters, with sodium alginate being preferred.

[0171] Examples of alkaline substances include alkali metal salts of inorganic or organic acids, alkaline earth metal salts, and compounds that liberate alkali when heated, with alkali metal hydroxides and alkali metal salts being preferred. Specific examples include alkali metal hydroxides such as sodium hydroxide and calcium hydroxide, alkali metal salts of inorganic compounds such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium dihydrogen phosphate, disodium hydrogen phosphate, and sodium phosphate, and alkali metal salts of organic compounds such as sodium formate and sodium trichloroacetate, with sodium bicarbonate being preferred.

[0172] The reduction inhibitor is preferably sodium meta-nitrobenzenesulfonate. Examples of the hydrotropic agent include urea and ureas such as dimethylurea, with urea being preferred.

[0173] The sizing agent, alkaline substance, reduction inhibitor, and hydrotropic agent may be used either alone or in combination of two or more.

[0174] The mixing ratio of each component in the pretreatment liquid is, for example, 0.5 to 5 mass% of sizing agent, 0.5 to 5 mass% of sodium bicarbonate, 0 to 5 mass% of sodium metanitrobenzenesulfonate, 1 to 20 mass% of urea, and the remainder is water.

[0175] The method for applying the pretreatment liquid to the hydrophobic fibers includes, for example, a padding method, in which the squeezing rate is preferably about 40 to 90%, more preferably about 60 to 80%. [Example]

[0176] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "parts" and "%" refer to parts by mass and mass%, respectively. The aqueous dispersions and inks using the same in each example are both included in the above-mentioned colored dispersions.

[0177] <Preparation Example 1: Preparation of NaOH Neutralized Joncryl 678> Joncryl 678 (manufactured by BASF) (20 parts) was added to a mixture of 25% sodium hydroxide (6 parts), ion-exchanged water (54 parts), and propylene glycol (20 parts), and the mixture was heated to 90 to 120°C and stirred for 5 hours to obtain a NaOH-neutralized product of Joncryl 678.

[0178] <Preparation Example 2: Preparation of NaOH Neutralized Joncryl JDX-300C> Joncryl JDX-300C (manufactured by BASF) (20 parts) was added to a mixture of 25% sodium hydroxide (6 parts), ion-exchanged water (54 parts), and propylene glycol (20 parts), and the mixture was heated to 90 to 120°C and stirred for 5 hours to obtain a NaOH-neutralized product of Joncryl JDX-300C.

[0179] <Examples 1a to 29a: Preparation of aqueous dispersions 1a to 29a> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Tables 1 to 4 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 1a to 29a.

[0180] <Comparative Examples 1a to 9a: Preparation of Aqueous Dispersions 30a to 38a> Glass beads with a diameter of 0.2 mm were added to a mixture of the components listed in Table 5 below, and the mixture was dispersed in a sand mill for approximately 30 hours under water cooling. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 30a to 38a.

[0181] The numerical values ​​of each component in Tables 1 to 5 represent parts by mass. The abbreviations in Tables 1 to 5 represent the following: DB359: CI Disperse Blue 359 SB35: CI Solvent Blue 35 SB36: CI Solvent Blue 36 SB78: CI Solvent Blue 78 SB102: CI Solvent Blue 102 SB105: CI Solvent Blue 105 SB112: CI Solvent Blue 112 SB12: CI Solvent Blue 12 SB13: CI Solvent Blue 13 SB58: CI Solvent Blue 58 SB63: CI Solvent Blue 63 SB83: CI Solvent Blue 83 SB86: CI Solvent Blue 86 SB94: CI Solvent Blue 94 SB111: CI Solvent Blue 111 TS-2000: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-57: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Labelin W-40: Creosote oil sodium sulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin FD-40: sodium naphthalenesulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin MN-40: Methylnaphthalenesulfonate sodium formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Demol SC-30: Sodium meta-cresol sulfonate formalin condensate (Kao Corporation) Morwet D425: Sodium alkylnaphthalene sulfonate formalin condensate (manufactured by Lion Specialty Chemicals Co., Ltd.) Zetasperse 3100: Polymeric resin dispersant (Evonik Japan Co., Ltd.) BYK-190: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) BYK-2015: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) TEGODISPER 755W: Polymer resin dispersant (manufactured by Evonik Japan Co., Ltd.) Solsperse 46000: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) Solsperse J400: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) TS-1500: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-210: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Nikkol BPS-30: Ethylene oxide adduct of phytosterol (manufactured by Nikko Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza) Surfynol 104PG50: Surfynol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to a concentration of 50%.

[0182] [Table 1]

[0183] [Table 2]

[0184] [Table 3]

[0185] [Table 4]

[0186] [Table 5]

[0187] Examples 30a to 58a: Preparation of Inks 1a to 29a Inks 1a to 29a were prepared by mixing the aqueous dispersions 1a to 29a obtained in Examples 1a to 29a with the components listed in Tables 6 to 9 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0188] Comparative Examples 10a to 18a: Preparation of Inks 30a to 38a Inks 30a to 38a were prepared by mixing the aqueous dispersions 30a to 38a obtained in Comparative Examples 1a to 9a with the components listed in Table 10 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0189] The numerical values ​​of each component in Tables 6 to 10 represent parts by mass. The abbreviations in Tables 6 to 10 represent the following: BYK-348: Polyether-modified polydimethylsiloxane (manufactured by BYK Japan Co., Ltd.) TEA-80: Triethanolamine (Oxalis Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza)

[0190] [Table 6]

[0191] [Table 7]

[0192] [Table 8]

[0193] [Table 9]

[0194] [Table 10]

[0195] <Examples 59a to 64a and Comparative Example 19a: Preparation of aqueous dispersions 39a to 45a> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Table 11 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 39a to 45a.

[0196] The numerical values ​​of each component in Table 11 represent parts by mass. The abbreviations in Table 11 have the same meanings as in Tables 1 to 5.

[0197] [Table 11]

[0198] <Examples 65a to 70a and Comparative Examples 20a to 21a: Preparation of Inks 39a to 46a> Inks 39a to 46a were prepared by mixing aqueous dispersions 30a and 39a to 45a obtained in Comparative Example 1a, Examples 59a to 64a, and Comparative Example 19a with the components listed in Table 12 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0199] The numerical values ​​of each component in Table 12 represent parts by mass. The abbreviations in Table 12 have the same meanings as in Tables 6 to 10.

[0200] [Table 12]

[0201] <Evaluation> The aqueous dispersions 1a to 45a and inks 1a to 46a prepared as described above were used to carry out the following evaluation tests, and the results are shown in Tables 1 to 12 above.

[0202] [Particle size change test] The median particle size (D50, number average particle size) of the colorant in each aqueous dispersion or ink stored at 60°C for 5 days was measured using a MICRO TRAC UPA EX150 (manufactured by Micro Track Bell Co., Ltd.) and evaluated according to the following criteria: A or B indicates good storage stability, and C or D indicates poor storage stability. -Evaluation criteria- A: D50 is less than 140nm B: D50 is 140nm or more and less than 160nm C: D50 is 160nm or more and less than 170nm D:D50 is 170nm or more

[0203] [Sedimentation test] The sedimentation rate was calculated according to the following formula using the absorbance Abs0 at the maximum absorption wavelength (λmax) around 574 nm measured when the ink was prepared, and the absorbance Abs1 at the maximum absorption wavelength (λmax) around 574 nm measured by taking an aliquot of the supernatant of the ink stored at 60°C for 5 days. The absorbance was measured using a UV-visible spectrophotometer (UV-2550, manufactured by Shimadzu Corporation) after diluting the ink 2000 times with ion-exchange water. Sedimentation rate (%) = {(Abs0-Abs1) / Abs0} x 100 The calculated sedimentation rate was then evaluated according to the following criteria: A or B indicates good storage stability, and C indicates poor storage stability. -Evaluation criteria- A: Sedimentation rate is less than 5% B: Settling rate is 5% or more but less than 15% C: Sedimentation rate is 15% or more

[0204] [Redispersibility test] 25 μL of each aqueous dispersion or ink was dropped onto a glass petri dish and dried for 1 hour in a thermo-hygrostat at 60°C. 10 mL of ion-exchanged water was dropped onto the resulting dried product at room temperature, and the product was visually observed to determine whether it redispersed or not, and evaluated using the following four-level scale. The more redispersible the ink, the easier it is to eliminate clogging after drying, and therefore the better the ink. A, B, or C indicates good redispersibility, and D indicates poor redispersibility. -Evaluation criteria- A: No residue left, everything redispersed. B: A small amount of residue remains, but most of it has been redispersed. C: A large amount of residue remains, but it has been redispersed to some extent. D: Not redispersed at all.

[0205] As is clear from the results in Tables 1 to 12, the aqueous dispersions of Examples 1a to 29a and 59a to 64a, and the inks prepared therefrom of Examples 30a to 58a and 65a to 70a, did not significantly increase in particle size during high-temperature storage, and therefore had few coarse particles, good sedimentation properties, and excellent storage stability. On the other hand, the aqueous dispersions of Comparative Examples 1a to 9a and 19a, and the inks prepared therefrom of Comparative Examples 10a to 18a and 20a to 21a, were inferior in storage stability to the Examples.

[0206] Furthermore, the evaluation results of the aqueous dispersions of Examples 1a to 7a, 24a to 29a, and 59a to 64a, and the inks prepared using them of Examples 30a to 36a, 53a to 58a, and 65a to 70a, showed that redispersibility was improved by using a polyoxyethylene arylphenyl ether sulfate-based dispersant as a dispersant.

[0207] <Examples 1b to 29b: Preparation of aqueous dispersions 1b to 29b> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Tables 13 to 16 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 1b to 29b.

[0208] <Comparative Examples 1b to 9b: Preparation of Aqueous Dispersions 30b to 38b> Glass beads with a diameter of 0.2 mm were added to a mixture of the components listed in Table 17 below, and the mixture was dispersed in a sand mill for approximately 30 hours under water cooling. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 30b to 38b.

[0209] The numerical values ​​of each component in Tables 13 to 17 represent parts by mass. The abbreviations in Tables 13 to 17 represent the following: DY54: CI Disperse Yellow 54 DY64: CI Disperse Yellow 64 DY134: CI Disperse Yellow 134 DY143: CI Disperse Yellow 143 DY149: CI Disperse Yellow 149 DY160: CI Disperse Yellow 160 DY1: CI Disperse Yellow 1 DY9: CI Disperse Yellow 9 DY31: CI Disperse Yellow 31 DY33: CI Disperse Yellow 33 DY104: CI Disperse Yellow 104 DY119: CI Disperse Yellow 119 DY126: CI Disperse Yellow 126 TS-2000: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-57: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Labelin W-40: Creosote oil sodium sulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin FD-40: sodium naphthalenesulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin MN-40: Methylnaphthalenesulfonate sodium formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Demol SC-30: Sodium meta-cresol sulfonate formalin condensate (Kao Corporation) Morwet D425: Sodium alkylnaphthalene sulfonate formalin condensate (manufactured by Lion Specialty Chemicals Co., Ltd.) Zetasperse 3100: Polymeric resin dispersant (Evonik Japan Co., Ltd.) BYK-190: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) BYK-2015: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) TEGODISPER 755W: Polymer resin dispersant (manufactured by Evonik Japan Co., Ltd.) Solsperse 46000: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) Solsperse J400: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) TS-1500: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-210: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Nikkol BPS-30: Ethylene oxide adduct of phytosterol (manufactured by Nikko Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza) Surfynol 104PG50: Surfynol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to a concentration of 50%.

[0210] [Table 13]

[0211] [Table 14]

[0212] [Table 15]

[0213] [Table 16]

[0214] [Table 17]

[0215] <Examples 30b to 58b: Preparation of Inks 1b to 29b> Inks 1b to 29b were prepared by mixing the aqueous dispersions 1b to 29b obtained in Examples 1b to 29b with the components listed in Tables 18 to 21 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0216] Comparative Examples 10b to 18b: Preparation of Inks 30b to 38b Inks 30b to 38b were prepared by mixing the aqueous dispersions 30b to 38b obtained in Comparative Examples 1b to 9b with the components listed in Table 22 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0217] The numerical values ​​of each component in Tables 18 to 22 represent parts by mass. The abbreviations in Tables 18 to 22 represent the following: BYK-348: Polyether-modified polydimethylsiloxane (manufactured by BYK Japan Co., Ltd.) TEA-80: Triethanolamine (Oxalis Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza)

[0218] [Table 18]

[0219] [Table 19]

[0220] [Table 20]

[0221] [Table 21]

[0222] [Table 22]

[0223] <Examples 59b to 64b and Comparative Example 19b: Preparation of aqueous dispersions 39b to 45b> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Table 23 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 39b to 45b.

[0224] The numerical values ​​of each component in Table 23 represent parts by mass. The abbreviations in Table 23 have the same meanings as in Tables 13 to 17.

[0225] [Table 23]

[0226] <Examples 65b to 70b and Comparative Examples 20b to 21b: Preparation of Inks 39b to 46b> Inks 39b to 46b were prepared by mixing the aqueous dispersions 38b to 45b obtained in Comparative Example 9b, Examples 59b to 64b, and Comparative Example 19b with the components listed in Table 24 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0227] The numerical values ​​of each component in Table 24 represent parts by mass. The abbreviations in Table 24 have the same meanings as in Tables 18 to 22.

[0228] [Table 24]

[0229] <Evaluation> The aqueous dispersions 1b to 45b and inks 1b to 46b prepared as described above were used to carry out the following evaluation tests. The results are shown in Tables 13 to 22 above.

[0230] [Particle size change test] The median particle size (D50, number average particle size) of the colorant in each aqueous dispersion or ink stored at 60°C for 5 days was measured using a MICRO TRAC UPA EX150 (manufactured by Micro Track Bell Co., Ltd.) and evaluated according to the following criteria: A or B indicates good storage stability, and C or D indicates poor storage stability. -Evaluation criteria- A: D50 is less than 140nm B: D50 is 140nm or more and less than 160nm C: D50 is 160nm or more and less than 170nm D:D50 is 170nm or more

[0231] [Sedimentation test] The sedimentation rate was calculated according to the following formula using the absorbance Abs0 at the maximum absorption wavelength (λmax) around 408 nm measured when the ink was prepared, and the absorbance Abs1 at the maximum absorption wavelength (λmax) around 408 nm measured by taking an aliquot of the supernatant of the ink stored at 60°C for 5 days. The absorbance was measured using a UV-visible spectrophotometer (UV-2550, manufactured by Shimadzu Corporation) after diluting the ink 2000 times with ion-exchange water. Sedimentation rate (%) = {(Abs0-Abs1) / Abs0} x 100 The calculated sedimentation rate was then evaluated according to the following criteria: A or B indicates good storage stability, and C indicates poor storage stability. -Evaluation criteria- A: Sedimentation rate is less than 5% B: Settling rate is 5% or more but less than 15% C: Sedimentation rate is 15% or more

[0232] [Redispersibility test] 25 μL of each aqueous dispersion or ink was dropped onto a glass petri dish and dried for 1 hour in a thermo-hygrostat at 60°C. 10 mL of ion-exchanged water was dropped onto the resulting dried product at room temperature, and the product was visually observed to determine whether it redispersed or not, and evaluated using the following four-level scale. The more redispersible the ink, the easier it is to eliminate clogging after drying, and therefore the better the ink. A, B, or C indicates good redispersibility, and D indicates poor redispersibility. -Evaluation criteria- A: No residue left, everything redispersed. B: A small amount of residue remains, but most of it has been redispersed. C: A large amount of residue remains, but it has been redispersed to some extent. D: Not redispersed at all.

[0233] As is clear from the results in Tables 13 to 22, the aqueous dispersions of Examples 1b to 29b and 59b to 64b, and the inks prepared therefrom of Examples 30b to 58b and 65b to 70b, did not experience a significant increase in particle size during high-temperature storage, and therefore had few coarse particles, good sedimentation properties, and excellent storage stability. On the other hand, the aqueous dispersions of Comparative Examples 1b to 9b and 19b, and the inks prepared therefrom of Comparative Examples 10b to 18b and 20b to 21b, were inferior in storage stability to the Examples.

[0234] Furthermore, the evaluation results of the aqueous dispersions of Examples 1b to 7b, 24b to 29b, and 59b to 64b, and the inks prepared using them of Examples 30b to 36b, 53b to 58b, and 65b to 70b, showed that redispersibility was improved by using a polyoxyethylene arylphenyl ether sulfate-based dispersant as a dispersant.

[0235] <Examples 1c to 28c: Preparation of aqueous dispersions 1c to 28c> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Tables 25 to 28 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 1c to 28c.

[0236] <Comparative Examples 1c to 11c: Preparation of Aqueous Dispersions 29c to 39c> To a mixture of the components listed in Table 29 below, 0.2 mm diameter glass beads were added, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 29c to 39c.

[0237] The numerical values ​​of each component in Tables 25 to 29 represent parts by mass. The abbreviations in Tables 25 to 29 represent the following: SO60: CI Solvent Orange 60 SR179: CI Solvent Red 179 SR180: CI Solvent Red 180 DO118: CI Disperse Orange 118 DO25: CI Disperse Orange 25 DO56: CI Disperse Orange 56 DO73: CI Disperse Orange 73 DR60: CI Disperse Red 60 DY54: CI Disperse Yellow 54 TS-2000: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-57: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Labelin W-40: Creosote oil sodium sulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin FD-40: sodium naphthalenesulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin MN-40: Methylnaphthalenesulfonate sodium formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Demol SC-30: Sodium meta-cresol sulfonate formalin condensate (Kao Corporation) Morwet D425: Sodium alkylnaphthalene sulfonate formalin condensate (manufactured by Lion Specialty Chemicals Co., Ltd.) Zetasperse 3100: Polymeric resin dispersant (Evonik Japan Co., Ltd.) BYK-190: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) BYK-2015: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) TEGODISPER 755W: Polymer resin dispersant (manufactured by Evonik Japan Co., Ltd.) Solsperse 46000: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) Solsperse J400: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) TS-1500: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-210: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Nikkol BPS-30: Ethylene oxide adduct of phytosterol (manufactured by Nikko Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza) Surfynol 104PG50: Surfynol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to a concentration of 50%.

[0238] [Table 25]

[0239] [Table 26]

[0240] [Table 27]

[0241] [Table 28]

[0242] [Table 29]

[0243] Examples 29c to 56c: Preparation of Inks 1c to 28c The aqueous dispersions 1c to 28c obtained in Examples 1c to 28c were mixed with the components listed in Tables 30 to 33 below, stirred for 30 minutes, and then filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to prepare inks 1c to 28c, respectively.

[0244] Comparative Examples 12c to 22c: Preparation of Inks 29c to 39c Inks 29c to 39c were prepared by mixing aqueous dispersions 29c to 39c obtained in Comparative Examples 1c to 11c with the components listed in Table 34 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0245] The numerical values ​​of each component in Tables 30 to 34 represent parts by mass. The abbreviations in Tables 30 to 34 represent the following: BYK-348: Polyether-modified polydimethylsiloxane (manufactured by BYK Japan Co., Ltd.) TEA-80: Triethanolamine (Oxalis Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza)

[0246] [Table 30]

[0247] [Table 31]

[0248] [Table 32]

[0249] [Table 33]

[0250] [Table 34]

[0251] <Examples 57c to 63c and Comparative Example 23c: Preparation of aqueous dispersions 40c to 47c> Glass beads with a diameter of 0.2 mm were added to a mixture of the components listed in Table 35 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 40c to 47c.

[0252] The numerical values ​​of each component in Table 35 represent parts by mass. The abbreviations in Table 35 have the same meanings as in Tables 25 to 29.

[0253] [Table 35]

[0254] <Examples 64c to 70c and Comparative Examples 24c to 25c: Preparation of Inks 40c to 48c> The aqueous dispersions 29c, 40c to 47c obtained in Comparative Example 1c, Examples 57c to 63c, and Comparative Example 23c were mixed with the components listed in Table 36 below, stirred for 30 minutes, and then filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to prepare inks 40c to 48c, respectively.

[0255] The numerical values ​​of each component in Table 36 represent parts by mass. The abbreviations in Table 36 have the same meanings as in Tables 30 to 34.

[0256] [Table 36]

[0257] <Evaluation> The aqueous dispersions 1c to 47c and inks 1c to 48c prepared as described above were subjected to the following evaluation tests, and the results are shown in Tables 25 to 36 above.

[0258] [Particle size change test] The median particle size (D50, number average particle size) of the colorant in each aqueous dispersion or ink stored at 60°C for 5 days was measured using a MICRO TRAC UPA EX150 (manufactured by Micro Track Bell Co., Ltd.) and evaluated according to the following criteria: A or B indicates good storage stability, and C or D indicates poor storage stability. -Evaluation criteria- A: D50 is less than 140nm B: D50 is 140nm or more and less than 160nm C: D50 is 160nm or more and less than 170nm D:D50 is 170nm or more

[0259] [Sedimentation test] The sedimentation rate was calculated according to the following formula using the absorbance Abs0 at the maximum absorption wavelength (λmax) around 495 nm measured when the ink was prepared, and the absorbance Abs1 at the maximum absorption wavelength (λmax) around 495 nm measured by taking an aliquot of the supernatant of the ink stored at 60°C for 5 days. The absorbance was measured using a UV-visible spectrophotometer (UV-2550, manufactured by Shimadzu Corporation) after diluting the ink 500-fold with ion-exchange water. Sedimentation rate (%) = {(Abs0-Abs1) / Abs0} x 100 The calculated sedimentation rate was then evaluated according to the following criteria: A or B indicates good storage stability, and C indicates poor storage stability. -Evaluation criteria- A: Sedimentation rate is less than 5% B: Settling rate is 5% or more but less than 15% C: Sedimentation rate is 15% or more

[0260] [Redispersibility test] 25 μL of each aqueous dispersion or ink was dropped onto a glass petri dish and dried for 1 hour in a thermo-hygrostat at 60°C. 10 mL of ion-exchanged water was dropped onto the resulting dried product at room temperature, and the product was visually observed to determine whether it redispersed or not, and evaluated using the following four-level scale. The more redispersible the ink, the easier it is to eliminate clogging after drying, and therefore the better the ink. A, B, or C indicates good redispersibility, and D indicates poor redispersibility. -Evaluation criteria- A: No residue left, everything redispersed. B: A small amount of residue remains, but most of it has been redispersed. C: A large amount of residue remains, but it has been redispersed to some extent. D: Not redispersed at all.

[0261] As is clear from the results in Tables 25 to 36, the aqueous dispersions of Examples 1c to 28c and 57c to 63c, and the inks prepared therefrom of Examples 29c to 56c and 64c to 70c, did not experience a significant increase in particle size during high-temperature storage, and therefore had few coarse particles, good sedimentation properties, and excellent storage stability. On the other hand, the aqueous dispersions of Comparative Examples 1c to 11c and 23c, and the inks prepared therefrom of Comparative Examples 12c to 22c and 24c to 25c, were inferior in storage stability to the Examples.

[0262] Furthermore, the evaluation results of the aqueous dispersions of Examples 1c to 6c, 23c to 28c, and 57c to 63c, and the inks prepared using them of Examples 29c to 34c, 51c to 56c, and 64c to 70c, showed that redispersibility was improved by using a polyoxyethylene arylphenyl ether sulfate-based dispersant as a dispersant.

[0263] <Synthesis Example 1: Synthesis of compound represented by formula (10)> (Step 1: Synthesis of compound represented by formula (20)) m-Chloroaniline (6.4 parts), potassium carbonate (13.8 parts), and iodoethane (18.7 parts) were added to N,N-dimethylformamide (30 parts), and the mixture was heated to 100°C and reacted for 6 hours. After cooling to 60°C, water (100 parts) was added to the resulting reaction liquid, and extraction was performed three times with toluene (50 parts). The resulting organic layer was washed three times with water (100 parts), and the toluene was removed using an evaporator. The residue was then dried to obtain a compound (10 parts) represented by the following formula (20).

[0264] [ka]

[0265] (Step 2: Synthesis of compound represented by formula (10)) 2-Ethyl-4-nitroaniline (4.1 parts) was added to 96% sulfuric acid (20 parts) and stirred at 30-40°C for 30 minutes to dissolve. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (7.2 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. The compound represented by formula (20) (14.6 parts) obtained in step 1 above was added to 50% aqueous methanol (100 parts) and stirred at below 5°C for 30 minutes. The diazonium salt solution prepared above was added to this liquid, adjusted to pH 2.0 with 25% liquid caustic soda, and reacted for 3 hours at pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by formula (13) (10.2 parts).

[0266] [ka]

[0267] <Synthesis Example 2: Synthesis of compound represented by formula (11)> 2-Amino-5-nitrothiazole (6.9 parts) was added to 96% sulfuric acid (30 parts) and stirred at 30-40°C for 30 minutes to dissolve. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (17 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. The compound represented by formula (20) (7.6 parts) obtained in (Step 1) of Synthesis Example 1 above was added to 50% aqueous methanol (100 parts) and stirred for 30 minutes at below 5°C. The diazonium salt solution prepared above was added to this liquid, adjusted to pH 2.0 with 25% liquid caustic soda, and reacted for 3 hours under conditions of pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by formula (11) (6.2 parts).

[0268] [ka]

[0269] <Synthesis Example 3: Synthesis of compound represented by formula (12)> 2-Methyl-4-nitroaniline (16.7 parts) and 35% hydrochloric acid (34.4 parts) were added to ice water (100 parts) and stirred at 0 to 10°C for 30 minutes. 40% sodium nitrite (19.9 parts) was added at the same temperature and stirred for 1 hour. To the resulting reaction solution was added the compound represented by formula (20) (18.2 parts) obtained in Synthesis Example 1 (Step 1) above, and the reaction was carried out at pH 2.0 to 2.5 and 0 to 10°C for 2 hours, and then at pH 3.0 to 3.5 and 0 to 10°C for 2 hours. After the reaction was completed, the mixture was filtered and washed with water to obtain a compound represented by formula (12) (19.2 parts).

[0270] [ka]

[0271] <Synthesis Example 4: Synthesis of compound represented by formula (13)> 2,4,6-Trichloroaniline (8.0 parts) was added to 96% sulfuric acid (50 parts) and stirred at 30-40°C for 30 minutes to dissolve. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (12 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. N,N-Diethyl-m-toluidine (6.6 parts) was added to 50% aqueous methanol (100 parts) and stirred at below 5°C for 30 minutes. The diazonium salt solution prepared above was added to this liquid, adjusted to pH 2.0 with 25% liquid caustic soda, and reacted for 3 hours under conditions of pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by the following formula (13) (12.2 parts).

[0272] [ka]

[0273] <Synthesis Example 5: Synthesis of compound represented by formula (14)> p-Nitroaniline (8.2 parts) and 35% hydrochloric acid (18.8 parts) were added to ice water (50 parts) and stirred at 0 to 10°C for 30 minutes. 40% sodium nitrite (10.9 parts) was added at the same temperature and stirred for 1 hour. The compound represented by formula (20) (10 parts) obtained in Synthesis Example 1 (Step 1) above was added to the resulting reaction solution and reacted for 2 hours at pH 2.0 to 2.5 and 0 to 10°C, and then for 2 hours at pH 3.0 to 3.5 and 0 to 10°C. After the reaction was completed, the mixture was filtered and washed with water to obtain a compound represented by formula (14) (15.0 parts).

[0274] [ka]

[0275] <Synthesis Example 6: Synthesis of compound represented by formula (15)> (Step 1: Synthesis of compound represented by formula (21)) m-Bromoaniline (8.6 parts), potassium carbonate (13.8 parts), and iodoethane (18.7 parts) were added to N,N-dimethylformamide (30 parts), and the mixture was heated to 100°C and reacted for 6 hours. After cooling to 60°C, water (100 parts) was added to the resulting reaction liquid, and extraction was performed three times with toluene (50 parts). The resulting organic layer was washed three times with water (100 parts), and the toluene was removed using an evaporator. The residue was then dried to obtain a compound (11 parts) represented by the following formula (21).

[0276] [ka]

[0277] (Step 2: Synthesis of compound represented by formula (15)) p-Nitroaniline (8.2 parts) and 35% hydrochloric acid (18.8 parts) were added to ice water (50 parts) and stirred at 0 to 10°C for 30 minutes. 40% sodium nitrite (10.9 parts) was added at the same temperature and stirred for 1 hour. The compound represented by formula (21) (11 parts) obtained in step 1 above was added to the resulting reaction solution and reacted for 2 hours at pH 2.0 to 2.5 and 0 to 10°C, and then for 2 hours at pH 3.0 to 3.5 and 0 to 10°C. After the reaction was completed, the mixture was filtered and washed with water to obtain a compound represented by formula (15) (14.0 parts).

[0278] [ka]

[0279] <Synthesis Example 7: Synthesis of compound represented by formula (16)> 2,6-Dichloro-p-nitroaniline (12.4 parts) was added to 96% sulfuric acid (60 parts) and stirred at 30-40°C for 30 minutes to dissolve. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (9.2 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. The compound represented by formula (20) (9.0 parts) obtained in Synthesis Example 1 (Step 1) above was added to 50% aqueous methanol (100 parts) and stirred at below 5°C for 30 minutes. The diazonium salt solution prepared above was added to this liquid, adjusted to pH 2.0 with 25% liquid caustic soda, and reacted for 3 hours under conditions of pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by formula (16) below (14.2 parts).

[0280] [ka]

[0281] <Synthesis Example 8: Synthesis of compound represented by formula (17)> 2-Aminothiazole (4 parts) was added to 96% sulfuric acid (35 parts) and dissolved by stirring at 30-40°C for 30 minutes. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (6.1 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. The compound represented by formula (20) (9.0 parts) obtained in (Step 1) of Synthesis Example 1 above was added to 50% aqueous methanol (100 parts) and stirred for 30 minutes at below 5°C. The diazonium salt solution prepared above was added to this liquid, and the pH was adjusted to 2.0 with 25% liquid caustic soda. The reaction was allowed to proceed for 3 hours at pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by formula (17) (5.0 parts).

[0282] [ka]

[0283] <Synthesis Example 9: Synthesis of compound represented by formula (18)> 3-Chloro-4-nitroaniline (5 parts) was added to 96% sulfuric acid (45 parts) and stirred at 30-40°C for 30 minutes to dissolve. After cooling to below 5°C in an ice-water bath, 43% nitrosyl nitrate (9.4 parts) was added at the same temperature and stirred for 1 hour to synthesize a diazonium salt. The compound represented by formula (20) (9.0 parts) obtained in Synthesis Example 1 (Step 1) above was added to 50% aqueous methanol (100 parts) and stirred at below 5°C for 30 minutes. The diazonium salt solution prepared above was added to this liquid, adjusted to pH 2.0 with 25% liquid caustic soda, and reacted for 3 hours under conditions of pH 2.0-2.5 and 0-10°C. After completion of the reaction, the mixture was filtered and washed with water to obtain a compound represented by formula (18) below (6.9 parts).

[0284] [ka]

[0285] <Examples 1d to 29d: Preparation of aqueous dispersions 1d to 29d> Glass beads with a diameter of 0.2 mm were added to a mixture of the components shown in Tables 37 to 40 below, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 1d to 29d.

[0286] <Comparative Examples 1d to 6d: Preparation of Aqueous Dispersions 30d to 35d> To a mixture of the components listed in Table 41 below, 0.2 mm diameter glass beads were added, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 30d to 35d.

[0287] The numerical values ​​of each component in Tables 37 to 41 represent parts by mass. The abbreviations in Tables 37 to 41 represent the following: DB360: CI Disperse Blue 360 DB366: CI Disperse Blue 366 DB341: CI Disperse Blue 341 TS-2000: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-57: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Labelin W-40: Creosote oil sodium sulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin FD-40: sodium naphthalenesulfonate formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Labelin MN-40: Methylnaphthalenesulfonate sodium formalin condensate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Demol SC-30: Sodium meta-cresol sulfonate formalin condensate (Kao Corporation) Morwet D425: Sodium alkylnaphthalene sulfonate formalin condensate (manufactured by Lion Specialty Chemicals Co., Ltd.) Zetasperse 3100: Polymeric resin dispersant (Evonik Japan Co., Ltd.) BYK-190: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) BYK-2015: Polymer resin dispersant (manufactured by BYK Japan Co., Ltd.) TEGODISPER 755W: Polymer resin dispersant (manufactured by Evonik Japan Co., Ltd.) Solsperse 46000: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) Solsperse J400: Polymer resin dispersant (manufactured by Lubrizol Japan Co., Ltd.) TS-1500: Polyoxyethylene styryl phenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.) SM-210: Polyoxyethylene styryl phenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.) Nikkol BPS-30: Ethylene oxide adduct of phytosterol (manufactured by Nikko Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza) Surfynol 104PG50: Surfynol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to a concentration of 50%.

[0288] [Table 37]

[0289] [Table 38]

[0290] [Table 39]

[0291] [Table 40]

[0292] [Table 41]

[0293] Examples 30d to 58d: Preparation of Inks 1d to 29d Inks 1d to 29d were prepared by mixing the aqueous dispersions 1d to 29d obtained in Examples 1d to 29d with the components listed in Tables 42 to 45 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0294] <Comparative Examples 7d to 12d: Preparation of Inks 30d to 35d> Inks 30d to 35d were prepared by mixing the aqueous dispersions 30d to 35d obtained in Comparative Examples 1d to 6d with the components listed in Table 46 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0295] The numerical values ​​of each component in Tables 42 to 46 represent parts by mass. The abbreviations in Tables 42 to 46 represent the following: BYK-348: Polyether-modified polydimethylsiloxane (manufactured by BYK Japan Co., Ltd.) TEA-80: Triethanolamine (Oxalis Chemicals Co., Ltd.) Proxel GXL: Antiseptic and antifungal agent (manufactured by Lonza)

[0296] [Table 42]

[0297] [Table 43]

[0298] [Table 44]

[0299] [Table 45]

[0300] [Table 46]

[0301] <Examples 59d to 65d and Comparative Example 13d: Preparation of aqueous dispersions 36d to 43d> To a mixture of the components listed in Table 47 below, 0.2 mm diameter glass beads were added, and the mixture was dispersed in a sand mill under water cooling for approximately 30 hours. The resulting solution was filtered through glass fiber filter paper GC-50 (manufactured by ADVANTEC) to obtain aqueous dispersions 36d to 43d.

[0302] The numerical values ​​of each component in Table 47 represent parts by mass. The abbreviations in Table 47 have the same meanings as in Tables 37 to 41.

[0303] [Table 47]

[0304] <Examples 66d to 72d and Comparative Examples 14d to 15d: Preparation of Inks 36d to 44d> Inks 36d to 44d were prepared by mixing aqueous dispersions 30d and 36d to 43d obtained in Comparative Example 1d, Examples 59d to 65d, and Comparative Example 13d with the components listed in Table 48 below, stirring for 30 minutes, and then filtering through glass fiber filter paper GC-50 (manufactured by ADVANTEC).

[0305] The numerical values ​​of each component in Table 48 represent parts by mass. The abbreviations in Table 48 have the same meanings as in Tables 42 to 46.

[0306] [Table 48]

[0307] <Evaluation> The aqueous dispersions 1d to 43d and inks 1d to 44d prepared as described above were used to carry out the following evaluation tests. The results are shown in Tables 37 to 48 above.

[0308] [Particle size change test] The median particle size (D50, number average particle size) of the colorant in each aqueous dispersion or ink stored at 60°C for 5 days was measured using a MICRO TRAC UPA EX150 (manufactured by Micro Track Bell Co., Ltd.) and evaluated according to the following criteria: A or B indicates good storage stability, and C or D indicates poor storage stability. -Evaluation criteria- A: D50 is less than 140nm B: D50 is 140nm or more and less than 160nm C: D50 is 160nm or more and less than 170nm D:D50 is 170nm or more

[0309] [Sedimentation test] The sedimentation rate was calculated according to the following formula using the absorbance Abs0 at the maximum absorption wavelength (λmax) around 580 nm measured when the ink was prepared, and the absorbance Abs1 at the maximum absorption wavelength (λmax) around 580 nm measured by taking an aliquot of the supernatant of the ink stored at 60°C for 5 days. The absorbance was measured using a UV-visible spectrophotometer (UV-2550, manufactured by Shimadzu Corporation) after diluting the ink 2000 times with ion-exchange water. Sedimentation rate (%) = {(Abs0-Abs1) / Abs0} x 100 The calculated sedimentation rate was then evaluated according to the following criteria: A or B indicates good storage stability, and C indicates poor storage stability. -Evaluation criteria- A: Sedimentation rate is less than 5% B: Settling rate is 5% or more but less than 15% C: Sedimentation rate is 15% or more

[0310] [Redispersibility test] 25 μL of each aqueous dispersion or ink was dropped onto a glass petri dish and dried for 1 hour in a thermo-hygrostat at 60°C. 10 mL of ion-exchanged water was dropped onto the resulting dried product at room temperature, and the product was visually observed to determine whether it redispersed or not, and evaluated using the following four-level scale. The more redispersible the ink, the easier it is to eliminate clogging after drying, and therefore the better the ink. A, B, or C indicates good redispersibility, and D indicates poor redispersibility. -Evaluation criteria- A: No residue left, everything redispersed. B: A small amount of residue remains, but most of it has been redispersed. C: A large amount of residue remains, but it has been redispersed to some extent. D: Not redispersed at all.

[0311] [Filterability test] The ink was stored at 60°C for 5 days and then filtered through a 0.8µm pore size filter (DISMIC-25CS, manufactured by ADVANTEC). The amount of filtrate until the filter became clogged and filtration was impossible was measured and evaluated using the following four-level scale. The ink with a larger amount of filtrate is superior, with fewer coarse particles. A or B indicates good filterability, and C indicates poor filterability. -Evaluation criteria- A: Filtration volume is 10g or more B: Filtration volume is 7.5g or more but less than 10g C: Filtration volume less than 7.5g

[0312] As is clear from the results in Tables 37 to 48, the aqueous dispersions of Examples 1d to 29d and 59d to 65d, and the inks prepared therefrom of Examples 30d to 58d and 66d to 72d, did not experience a significant increase in particle size during high-temperature storage, and therefore had few coarse particles, good sedimentation and filterability, and excellent storage stability. On the other hand, the aqueous dispersions of Comparative Examples 1d to 6d and 13d, and the inks prepared therefrom of Comparative Examples 7d to 12d and 14d to 15d, were inferior in storage stability to the Examples.

[0313] Furthermore, the evaluation results of the aqueous dispersions of Examples 1d to 7d, 24d to 29d, and 59d to 65d, and the inks prepared using them of Examples 30d to 36d, 53d to 58d, and 66d to 72d, showed that redispersibility was improved by using a polyoxyethylene arylphenyl ether sulfate-based dispersant as a dispersant.

Claims

1. (A) any one of the dyes C.I. Disperse Blue 359, C.I. Disperse Yellow 54, C.I. Solvent Orange 60, and C.I. Disperse Blue 360; (B) a dye derivative which is a compound represented by any one of the following formulas (2a), (2b), (2c-1), (2c-2), (2d-1) to (2d-3); and water; The combination of the dye (A) and the dye derivative (B) is any one of the following combinations (a) to (d): (a) A combination of C.I. Disperse Blue 359 and a compound represented by the following formula (2a): (b) A combination of C.I. Disperse Yellow 54 and a compound represented by the following formula (2b): (c) A combination of C.I. Solvent Orange 60 and at least one compound selected from the compounds represented by the following formula (2c-1) and the compounds represented by the following formula (2c-2): (d) A combination of C.I. Disperse Blue 360 ​​and at least one compound selected from the group consisting of a compound represented by the following formula (2d-1), a compound represented by the following formula (2d-2), and a compound represented by the following formula (2d-3): Either The color dispersion liquid has a content of the dye derivative (B) of 0.1 to 5 parts by mass when the total content of the dye (A) and the dye derivative (B) is 100 parts by mass. 【Chemistry 4】 (In formula (2a), R ５ａ , R ６ａ R each independently represents an alkyl group having 1 to 6 carbon atoms which may have a substituent. ７ａ , R ８ａ each independently represents a hydrogen atom or a halogen atom. 【Chemistry 5】 (In formula (2b), A ｂ represents a carbon atom or a nitrogen atom. n represents a value of 0 to 1. ３ｂ , R ４ｂ R each independently represents an aliphatic group which may have a substituent. ３ｂ , R ４ｂ may be bonded to each other to form a monocyclic or condensed ring which may have a substituent. ５ｂ R represents an aliphatic group which may have a substituent. ３ｂ , R ４ｂ , R ５ｂ may be bonded to each other to form a condensed ring which may have a substituent. ６ｂ , R ７ｂ R each independently represents a hydrogen atom, a hydroxyl group, or a bromine atom. ８ｂ , R ９ｂ R each independently represents an aliphatic group which may have a substituent. ８ｂ , R ９ｂ may be bonded to each other to form a monocyclic or condensed ring which may have a substituent. ｂ , R ３ｂ ~R ９ｂ The combination of the above 1 to 3 is not limited to the combination of the compound represented by the formula (1b). 【Chemistry 6】 (In formula (2c-1), R １１ｃ ~R １６ｃ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 6 carbon atoms, a halogen atom, or -NHR １７ｃ or a group represented by -OR １８ｃ R represents a group represented by the formula: １７ｃ , R １８ｃ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. 【Chemistry 7】 (In formula (2c-2), R １９ｃ ~R ２３ｃ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a halogen atom, or -OR ２４ｃ R represents a group represented by the formula: ２４ｃ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. 【Chemistry 8】 (In formula (2d-1), R １ｄ , R ２ｄ each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a cyano group. However, the case where R １ｄ , R ２ｄ simultaneously represent hydrogen atoms is excluded. R ３ｄ , R ４ｄ each independently represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, or a halogen atom.) 【Chemistry 9】 (In formula (2d-2), R ５ｄ , R ６ｄ each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms which may have a substituent. 【Chemistry 10】 (In formula (2d-3), R ７ｄ R represents a methoxy group or a hydrogen atom. ８ｄ is a halogen atom or -NHCOCH ３ R represents a group represented by the formula: ９ｄ , R １０ｄ represents an alkyl group having 1 to 2 carbon atoms which may have a substituent, or -C ２ H ４ O.C.O.C. ２ H ５ It represents a group represented by the following formula:

2. The color dispersion according to claim 1, wherein the content of the dye derivative (B) is 0.5 to 5 parts by mass when the total content of the dye (A) and the dye derivative (B) is 100 parts by mass.

3. The color dispersion according to any one of claims 1 to 2, further comprising a dispersing agent.

4. 4. The color dispersion of claim 3, wherein the dispersant comprises a formalin condensate of an aromatic sulfonic acid or a salt thereof.

5. 5. The color dispersion according to claim 4, wherein the formalin condensate of an aromatic sulfonic acid or a salt thereof is a formalin condensate of sodium naphthalene sulfonate or a salt thereof.

6. 5. The colored dispersion according to claim 4, wherein the formalin condensate of an aromatic sulfonic acid or a salt thereof is a formalin condensate of a creosote oil sulfonic acid or a salt thereof.

7. The color dispersion of any one of claims 3 to 6, wherein the dispersing agent comprises a phytosterol compound.

8. 4. The color dispersion according to claim 3, wherein the dispersant comprises at least one selected from polyoxyethylene aryl phenyl ether-based dispersants and polyoxyethylene aryl phenyl ether sulfate-based dispersants.

9. A recording medium having the colored dispersion liquid according to any one of claims 1 to 8 adhered thereto.

10. The recording medium according to claim 9 , which is made of hydrophobic fibers.

11. A printing step in which droplets of the color dispersion according to any one of claims 1 to 8 are deposited on an intermediate recording medium to obtain a recorded image; a transfer step of contacting a hydrophobic fiber with a surface of the intermediate recording medium to which the color dispersion liquid has been applied and heat-treating the hydrophobic fiber to transfer the recorded image to the hydrophobic fiber; A method for printing hydrophobic fibers comprising the steps of:

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