Dyeing inkjet ink composition

Abstract

To provide a dyeing inkjet ink composition having excellent discharge stability and superior wash fastness of a printed product.SOLUTION: A dyeing inkjet ink composition comprises a colorant represented by formula (1), a water-soluble organic solvent, and a nitrogen-containing heterocyclic compound, wherein a total content x (mass%) of the nitrogen-containing heterocyclic compound relative to a total amount of the ink composition satisfies the following relational expression (A): 0<x≤0.5 (A).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an inkjet ink composition for textile printing. [Background technology]

[0002] The inkjet method is not only used to record images on paper, etc., but also to print fabrics, and various inkjet printing methods have been studied. Inkjet inks for printing contain coloring materials, such as dyes and pigments, to obtain images of desired colors. In addition, many studies have been conducted on inks and recording methods for inkjet printing.

[0003] For example, Patent Document 1 describes an inkjet ink that uses a phthalocyanine dye having a monochlorotriazine group. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent Publication No. 2021-116310 Summary of the Invention [Problem to be solved by the invention]

[0005] The inkjet ink described in Patent Document 1 uses a phthalocyanine dye having a monochlorotriazine group, which allows it to dye fabric and produce images with good color development. However, it tends to have poor washing fastness and can sometimes result in poor ejection stability in inkjet printing. [Means for solving the problem]

[0006] One embodiment of the inkjet ink composition for textile printing according to the present invention comprises: The inkjet ink composition for textile printing comprises A colorant represented by the following formula (1), a water-soluble organic solvent; a nitrogen-containing heterocyclic compound; Contains The total content x (mass %) of the nitrogen-containing heterocyclic compounds relative to the total amount of the ink composition satisfies the following relational expression (A). 0 <x≦0.5 ···(A)

[0007] [ka] ...Equation (1)

[0008] (In formula (1), a plurality of Ys are each independently a reactive group having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups, or SO2NH2 or SO3X; Xs are independently Na, K, or Li; when the number of reactive groups having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups as Y is a, the number of SO2NH2s is b, and the number of SO3Xs is c, a, b, and c satisfy the following relationship: a=1 to 2, b=0 to 2, c=1 to 3, a+b+c=4) [Brief explanation of the drawings]

[0009] [Figure 1] Table 1 shows the compositions and evaluation results of the examples. [Figure 2] Table 2 shows the compositions and evaluation results of comparative examples. DETAILED DESCRIPTION OF THE INVENTION

[0010] The following describes embodiments of the present invention. The embodiments described below are examples of the present invention. The present invention is not limited to the following embodiments, and includes various modified forms that are implemented within the scope of the present invention. Note that not all of the configurations described below are necessarily essential configurations of the present invention.

[0011] 1. Inkjet ink composition for textile printing The inkjet ink composition for textile printing according to this embodiment contains a colorant represented by the following formula (1), a water-soluble organic solvent, and a nitrogen-containing heterocyclic compound, and the total content x (mass %) of the nitrogen-containing heterocyclic compound relative to the total amount of the ink composition satisfies the following relational formula (A): 0 <x≦0.5 ···(A)

[0012] [ka] ...Equation (1)

[0013] (In formula (1), a plurality of Ys are each independently a reactive group having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups, or SO2NH2 or SO3X; Xs are independently Na, K, or Li; when the number of Ys that are reactive groups having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups is a, the number of SO2NH2s is b, and the number of SO3Xs is c, a, b, and c satisfy the following relationship: a=1 to 2, b=0 to 2, c=1 to 3, a+b+c=4) (Note that numerical ranges expressed using "to" are inclusive of both ends.)

[0014] 1.1. Colorant represented by formula (1) In the explanation of formula (1), the group that can be converted into a vinyl sulfone group is: -S(=O)2-CH2-CH2-OS(=O)2ONa, or -S(=O)2-CH2-CH2-OH Examples include:

[0015] Examples of colorants represented by formula (1) include CI Reactive Blue 15:1, CI Reactive Blue 15, CI Reactive Blue 72, and CI Reactive Blue 21. CI Reactive Blue 21 has -S(=O)2-CH2-CH2-OS(=O)2ONa as a group that can be converted to a vinyl sulfone group.

[0016] Furthermore, in the colorant represented by formula (1), when Y is a reactive group having one or more monochlorotriazine groups, the reactive group having one or more monochlorotriazine groups preferably has any of the structures of the following formulas (2) to (4).

[0017] [ka] ...Equation (2)

[0018] [ka] ...Equation (3)

[0019] [ka] ...Equation (4)

[0020] The above-mentioned CI Reactive Blue 15:1 has a reactive group having the structure of the above formula (2), CI Reactive Blue 15 has a reactive group having the structure of the above formula (3), and CI Reactive Blue 72 has a reactive group having the structure of the above formula (4).

[0021] A plurality of coloring materials represented by formula (1) can be used in combination. The total content of the coloring materials represented by formula (1) is preferably from 3% to 20% by mass, more preferably from 5% to 15% by mass, and even more preferably from 7% to 13% by mass, based on the total amount of the inkjet ink composition for textile printing.

[0022] 1.2. Water-soluble organic solvents The inkjet ink composition for textile printing according to this embodiment contains a water-soluble organic solvent.

[0023] The water-soluble organic solvent is not limited as long as it is water-soluble, and examples thereof include esters, alkylene glycol ethers, cyclic esters, nitrogen-containing solvents, polyhydric alcohols, etc. Examples of the nitrogen-containing solvent include cyclic amides and non-cyclic amides. Examples of the non-cyclic amides include alkoxyalkylamides.

[0024] Examples of the esters include glycol monoacetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol monobutyl ether acetate, and glycol diesters such as ethylene glycol diacetate, diethylene glycol diacetate, and propylene glycol diacetate.

[0025] The alkylene glycol ethers may be monoethers or diethers of alkylene glycol, and alkyl ethers are preferred. Specific examples include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monoethyl ether, triethylene glycol monoisopropyl ether, and triethylene glycol monobutyl ether, and alkylene glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether.

[0026] Examples of cyclic esters include cyclic esters (lactones) such as β-propiolactone, γ-butyrolactone, δ-valerolactone, ε-caprolactone, and β-butyrolactone, as well as compounds in which the hydrogen atom of the methylene group adjacent to the carbonyl group of these cyclic esters is substituted with an alkyl group having 1 to 4 carbon atoms.

[0027] Examples of alkoxyalkylamides include 3-methoxy-N,N-dimethylpropionamide, 3-methoxy-N,N-diethylpropionamide, 3-methoxy-N,N-methylethylpropionamide, 3-ethoxy-N,N-dimethylpropionamide, 3-ethoxy-N,N-diethylpropionamide, 3-ethoxy-N,N-methylethylpropionamide, 3-n-butoxy-N,N-dimethylpropionamide, 3-n-butoxy-N,N-diethylpropionamide, and 3-n-butoxy-N,N-methylethylpropionamide.

[0028] Examples of cyclic amides include lactams, such as pyrrolidones such as 2-pyrrolidone, 1-methyl-2-pyrrolidone, 1-ethyl-2-pyrrolidone, 1-propyl-2-pyrrolidone, and 1-butyl-2-pyrrolidone.

[0029] It is also preferable to use a compound represented by the following general formula (1) as the alkoxyalkylamide.

[0030] R 1 -O-CH2CH2-(C=O)-NR 2 R 3 ···(1)

[0031] In the above formula (1), R 1 represents an alkyl group having 1 to 4 carbon atoms, and R 2 and R 3each independently represents a methyl group or an ethyl group. The "alkyl group having 1 to 4 carbon atoms" can be a linear or branched alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, or a tert-butyl group. The compound represented by the above formula (1) may be used alone or in combination of two or more types.

[0032] Examples of polyhydric alcohols include 1,2-alkanediols (e.g., alkanediols such as ethylene glycol, propylene glycol (also known as propane-1,2-diol), 1,2-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, and 1,2-octanediol), and polyhydric alcohols (polyols) other than 1,2-alkanediols (e.g., diethylene glycol, dipropylene glycol, 1,3-propanediol, and 1,3-butanediol (also known as 1,3-butylene glycol)). glycol), 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2-ethyl-2-methyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 3-methyl-1,3-butanediol, 2-ethyl-1,3-hexanediol, 3-methyl-1,5-pentanediol, 2-methylpentane-2,4-diol, trimethylolpropane, glycerin, etc.

[0033] Examples of polyhydric alcohols include alkanediols and polyols. Alkanediols are diols of alkanes having 5 or more carbon atoms. The number of carbon atoms in the alkanes is preferably 5 to 15, more preferably 6 to 10, and even more preferably 6 to 8. 1,2-alkanediols are preferred.

[0034] The polyols are polyols of alkanes having 4 or less carbon atoms, or intermolecular condensation products of hydroxyl groups of polyols of alkanes having 4 or less carbon atoms. The number of carbon atoms of the alkane is preferably 2 to 3. The number of hydroxyl groups in the polyol molecule is 2 or more, preferably 5 or less, and more preferably 3 or less. When the polyol is the above-mentioned intermolecular condensation product, the number of intermolecular condensation groups is 2 or more, preferably 4 or less, and more preferably 3 or less. The polyhydric alcohols can be used alone or in combination of two or more.

[0035] Alkanediols and polyols can function mainly as penetrating solvents and / or moisturizing solvents, but alkanediols tend to have stronger penetrating solvent properties, while polyols tend to have stronger moisturizing solvent properties.

[0036] The total content of the water-soluble organic solvents is preferably from 2 to 30% by mass, more preferably from 5 to 25% by mass, and even more preferably from 10 to 20% by mass, based on the total amount of the inkjet ink composition for textile printing.

[0037] 1.3.Nitrogen-containing heterocyclic compounds The inkjet ink composition for textile printing according to this embodiment contains a nitrogen-containing heterocyclic compound. The nitrogen-containing heterocyclic compound is a compound having a heterocycle containing nitrogen, and may be saturated or unsaturated.

[0038] Examples of the nitrogen-containing heterocyclic compound include pyridine, quinoline, isoquinoline, quinoxaline, tetrahydroquinoline, pyrimidine, pyrazine, quinazoline, isoindoline, tryptamine, piperazine, piperidone, piperidine, prolinol, triazole, triazine, tetrazole, imidazole, morpholine, purine, adenine, guanine, hypoxanthine, xanthine, theobromine, caffeine, uric acid, and isoguanine, each of which may have a substituent.

[0039] When the nitrogen-containing heterocyclic compound is selected from the above-mentioned exemplary compounds, it is more preferable to select it from 3- to 6-membered monocyclic compounds, fused ring compounds having 2 to 3 3-membered ring structures, and compounds having substituents thereon. Furthermore, in this case, the 3- to 6-membered monocyclic compounds, the fused ring compounds having 2 to 3 3-membered ring structures, and compounds having substituents thereon preferably have a weight average molecular weight (Mw) of 200 or less.

[0040] When the nitrogen-containing heterocyclic compound is selected from the above-exemplified compounds, the ejection stability in inkjet printing and the washing fastness of the resulting printed matter can be improved.

[0041] Furthermore, as the nitrogen-containing heterocyclic compound, a compound represented by the following formula (5) may be used.

[0042] [ka] ...Equation (5)

[0043] (In formula (5), a plurality of Ys each independently represent a reactive group having one or more monochlorotriazine groups, SO2NH2, SO3Na, or H. When the number of reactive groups having one or more monochlorotriazine groups as Y is d, the number of SO2NH2s is e, the number of SO3Nas is f, and the number of Hs is g, d, e, f, and g satisfy the following relationship: d=1 to 2, e=0 to 2, f=1 to 3, g=1 to 3, and d+e+f+g=4.)

[0044] In the inkjet ink composition for textile printing of this embodiment, the nitrogen-containing heterocyclic compound preferably contains one or more compounds selected from the group consisting of a compound represented by formula (5), a 3- to 6-membered monocyclic compound, a fused ring compound having two or three 3- to 6-membered ring structures, and compounds having substituents thereon.

[0045] Furthermore, the inkjet ink composition for textile printing of this embodiment more preferably contains, as the nitrogen-containing heterocyclic compound, one or more compounds selected from the group consisting of a compound represented by formula (5), isoindoline, tryptamine, 2-methylpiperazine, and prolinol.

[0046] When the inkjet ink composition for textile printing contains such a nitrogen-containing heterocyclic compound, the ejection stability in inkjet printing and the washing fastness of the resulting recorded matter can be further improved.

[0047] In the inkjet ink composition for textile printing according to this embodiment, the total content x (mass %) of the nitrogen-containing heterocyclic compounds relative to the total amount of the ink composition satisfies the following relational expression (A). 0 <x≦0.5 ···(A)

[0048] That is, in the inkjet ink composition for textile printing according to this embodiment, the total content of the nitrogen-containing heterocyclic compounds described above is more than 0% by mass and 0.5% by mass or less relative to the total amount of the ink composition.

[0049] This makes it possible to improve the ejection stability in ink jetting and the washing fastness of the resulting recorded matter.

[0050] Furthermore, in the inkjet ink composition for textile printing according to this embodiment, the total content x (mass %) of the nitrogen-containing heterocyclic compounds described above preferably satisfies the following relational expression: 0.01≦x (B)

[0051] That is, in the inkjet ink composition for textile printing according to this embodiment, the total content of the nitrogen-containing heterocyclic compounds described above relative to the total amount of the ink composition is preferably 0.01% by mass or more.

[0052] Furthermore, in the inkjet ink composition for textile printing according to this embodiment, the total content of the nitrogen-containing heterocyclic compounds relative to the total amount of the ink composition is more preferably 0.01% by mass or more and 0.4% by mass or less, even more preferably 0.1% by mass or more and 0.3% by mass or less, and even more preferably 0.2% by mass or more and 0.3% by mass or less.

[0053] This makes it possible to further improve the ejection stability in ink jetting and the washing fastness of the resulting recorded matter.

[0054] 1.4.Other Ingredients The inkjet ink composition for textile printing of this embodiment may contain the following components.

[0055] (surfactant) The inkjet ink composition for textile printing may contain a surfactant. The surfactant adjusts the surface tension of the composition and functions to, for example, adjust the wettability with fabric. Among surfactants, for example, acetylene glycol-based surfactants, silicone-based surfactants, and fluorine-based surfactants can be preferably used.

[0056] The acetylene glycol surfactant is not particularly limited, but examples thereof include Surfynol 104, 104E, 104H, 104A, 104BC, 104DPM, 104PA, 104PG-50, 104S, 420, 440, 465, 485, SE, SE-F, 504, 61, DF37, CT111, CT121, CT131, CT136, TG, GA, and DF110D (all trade names, manufactured by Air Products & Chemicals Co.). , Olfine B, Y, P, A, STG, SPC, E1004, E1010, PD-001, PD-002W, PD-003, PD-004, EXP.4001, EXP.4036, EXP.4051, AF-103, AF-104, AK-02, SK-14, AE-3 (all trade names, manufactured by Nissin Chemical Industry Co., Ltd.), Acetylenol E00, E00P, E40, E100 (all trade names, manufactured by Kawaken Fine Chemicals Co., Ltd.).

[0057] The silicone surfactant is not particularly limited, but a polysiloxane compound is preferred. The polysiloxane compound is not particularly limited, but for example, a polyether-modified organosiloxane is exemplified. Commercially available products of the polyether-modified organosiloxane include, for example, BYK-306, BYK-307, BYK-333, BYK-341, BYK-345, BYK-346, BYK-348 (all trade names, manufactured by BYK-Chemie Japan), KF-351A, KF-352A, KF-353, KF-354L, KF-355A, KF- 615A, KF-945, KF-640, KF-642, KF-643, KF-6020, X-22-4515, KF-6011, KF-6012, KF-6015, KF-6017 (all trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Silface SAG002, 005, 503A, 008 (all trade names, manufactured by Nissin Chemical Industry Co., Ltd.), and the like.

[0058] As the fluorine-based surfactant, it is preferable to use a fluorine-modified polymer, and specific examples include BYK-3440 (manufactured by BYK Japan), Surflon S-241, S-242, S-243 (all trade names, manufactured by AGC Seimi Chemical Co., Ltd.), and Futergent 215M (manufactured by Neos Corporation).

[0059] When the inkjet ink composition for textile printing contains a surfactant, multiple types of surfactants may be contained. When the inkjet ink composition for textile printing contains a surfactant, the content of the surfactant may be 0.1% by mass or more and 2% by mass or less, preferably 0.3% by mass or more and 1.5% by mass or less, and more preferably 0.4% by mass or more and 1.0% by mass or less, based on the total mass of the inkjet ink composition for textile printing.

[0060] In the inkjet ink composition for textile printing, the content of the coloring material is preferably 0.1% by mass or less relative to the total amount of the inkjet ink composition for textile printing. In other words, the inkjet ink composition for textile printing is preferably not used with the intention of coloring.

[0061] (additives) The inkjet ink composition for textile printing may contain additives such as pH adjusters, sugars, chelating agents, preservatives, antifungal agents, and rust inhibitors.

[0062] The pH adjuster is not particularly limited, and examples thereof include appropriate combinations of acids, bases, weak acids, and weak bases. Examples of acids and bases used in such combinations include inorganic acids such as sulfuric acid, hydrochloric acid, and nitric acid; inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, potassium dihydrogen phosphate, disodium hydrogen phosphate, potassium carbonate, sodium carbonate, sodium bicarbonate, and ammonia; organic bases such as triethanolamine, diethanolamine, monoethanolamine, tripropanolamine, triisopropanolamine, diisopropanolamine, and trishydroxymethylaminomethane (THAM); and organic acids such as adipic acid, citric acid, succinic acid, lactic acid, and N,N-bis(2-hydroxybenzoate). Other buffers that may be used include Good's buffers such as N-(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), morpholinoethanesulfonic acid (MES), carbamoylmethyliminobisacetic acid (ADA), piperazine-1,4-bis(2-ethanesulfonic acid) (PIPES), N-(2-acetamido)-2-aminoethanesulfonic acid (ACES), cholamine hydrochloride, N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (TES), acetamidoglycine, tricine, glycinamide, and bicine, as well as phosphate buffer, citrate buffer, and Tris buffer. Furthermore, among these, it is preferable that the pH adjuster contains, as part or all of a tertiary amine such as triethanolamine or triisopropanolamine, or a carboxyl group-containing organic acid such as adipic acid, citric acid, succinic acid or lactic acid, since this makes it possible to obtain a more stable pH buffering effect.

[0063] Specific examples of sugars include glucose, mannose, fructose, ribose, xylose, arabinose, galactose, aldonic acid, glucitol (sorbitol), maltose, cellobiose, lactose, sucrose, trehalose, and maltotriose.

[0064] Examples of chelating agents include ethylenediaminetetraacetic acid and salts thereof (disodium dihydrogen ethylenediaminetetraacetate, or nitrilotriacetate, hexametaphosphate, pyrophosphate, or metaphosphate of ethylenediamine, etc.).

[0065] Examples of preservatives and antifungal agents include sodium benzoate, sodium pentachlorophenol, sodium 2-pyridinethiol-1-oxide, sodium sorbate, sodium dehydroacetate, Proxel CRL, Proxel BDN, Proxel GXL, Proxel XL-2, Proxel IB, and Proxel TN (all trade names manufactured by Lonza Japan), and 4-chloro-3-methylphenol (such as Preventol CMK manufactured by Bayer).

[0066] Examples of the rust inhibitor include benzotriazole, acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite, etc. Among these, benzotriazole is particularly preferred.

[0067] Other additives include viscosity modifiers, antifungal agents, antioxidants, oxygen absorbers, and the like.

[0068] 1.5. Manufacturing and Properties Since the inkjet textile printing ink composition is applied to fabrics and the like by an inkjet method, its viscosity at 20°C is preferably 1.5 mPa·s or more and 15 mPa·s or less, more preferably 1.5 mPa·s or more and 7 mPa·s or less, and even more preferably 1.5 mPa·s or more and 5.5 mPa·s or less.

[0069] In order to ensure appropriate wetting and spreading properties on fabrics, etc., the inkjet ink composition for textile printing has a surface tension of 40 mN / m or less, preferably 38 mN / m or less, more preferably 35 mN / m or less, and even more preferably 30 mN / m or less at 25° C. The surface tension is preferably 20 mN / m or more, and more preferably 25 mN / m or more.

[0070] The surface tension can be measured by using an automatic surface tensiometer CBVP-Z (manufactured by Kyowa Interface Science Co., Ltd.) to check the surface tension when a platinum plate is wetted with the composition in an environment of 25°C.

[0071] The inkjet ink composition for textile printing can be obtained by mixing the above-mentioned components in any order and, if necessary, removing impurities by filtration or the like. A suitable method for mixing the components is to sequentially add the materials to a container equipped with a stirring device such as a mechanical stirrer or a magnetic stirrer and stir and mix them. As a filtration method, centrifugal filtration, filter filtration, etc. can be used as necessary.

[0072] 1.6. Mode of attachment The inkjet printing ink composition is applied to fabric or the like by an inkjet method. The amount of the inkjet printing ink composition to be applied is not limited, but may be, for example, 15 g / m 2 More than 120g / m 2 Less than 30 g / m 2 More than 80g / m 2 Less than 30 g / m is more preferable. 2 More than 60g / m 2 The following is even more preferred:

[0073] 1.7. Effects, etc. The inkjet printing ink composition according to this embodiment contains a colorant represented by formula (1), and therefore can dye fabric to produce an image with good color development. While recorded materials formed using a colorant represented by formula (1) generally tend to have poor washing fastness, the inkjet printing ink composition according to this embodiment contains a small amount of a nitrogen-containing heterocyclic compound, which improves the washing fastness of recorded materials without impairing the color development of the image. Furthermore, while the inclusion of a nitrogen-containing heterocyclic compound generally reduces inkjet ejection stability, the inkjet printing ink composition according to this embodiment contains a nitrogen-containing heterocyclic compound in an amount of 0.5% by mass or less, thereby achieving both good washing fastness and ejection stability.

[0074] 2. Examples and Comparative Examples The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Hereinafter, "parts" and "%" are by mass unless otherwise specified. The evaluations were carried out in an environment of 25°C and 40.0% relative humidity unless otherwise specified.

[0075] 2.1. Preparation of each composition Each example of an inkjet ink composition for textile printing was prepared as follows. The materials were mixed in the composition shown in the table and thoroughly stirred to obtain an ink composition. The values ​​shown are solid content concentrations in mass %, and the total is 100.0 mass %.

[0076] The abbreviations and product names shown in Tables 1 and 2 are explained below. RB15:1: CI Reactive Blue 15:1 (a compound with CAS No. 149343-84-0, having the reactive group of the above formula (2)) RB15: CI Reactive Blue 15 (a compound with CAS No. 12225-39-7, having the reactive group of the above formula (3)) RB72: CI Reactive Blue 72 (a compound with CAS No. 68967-01-1, having the reactive group of the above formula (4)) PB15: CI Pigment Blue 15 (a compound with CAS No. 147-14-8, which is an unsulfonated version of RB15, does not have the reactive group of the above formula (3), and all of the substituents on the phthalocyanine skeleton are H groups.) RB4: CI Reactive Blue 4 (CAS No. 13324-20-4), a compound that does not have a phthalocyanine skeleton. RB21: CI Reactive Blue 21 (CAS No. 12236-86-1 compound, containing a group that can be converted to a vinyl sulfone group) Compound A: A compound having 1 to 3 H groups in the phthalocyanine skeleton obtained by desulfonation treatment using RB15:1. Olfine PD002W: Nissin Chemical Industry Co., Ltd. Acetylene glycol surfactant Proxel XL-2: Preservative and antifungal agent manufactured by Lonza Japan

[0077] In Tables 1 and 2, the molecular weight of the substance is indicated as "Mw."

[0078] 2.2.Evaluation Method 2.2.1.Evaluation of ejection stability The following tests were carried out using an inkjet recording apparatus: PX-H6000 (manufactured by Seiko Epson Corporation). The ink compositions prepared according to the formulations of Examples 1 to 13 and Comparative Examples 1 to 4 were filled. After confirming that all nozzles of the evaluation machine were ejecting normally without missing or bending, continuous ejection was continued, and the ejection stability after 10 hours was evaluated as follows. The results are shown in the table. A rating of "C" or higher is considered to be good. A: All nozzles discharge normally B: Missing or bending occurs in less than 10% of the total number of nozzles C: Missing or bending occurs in less than 20% of the total number of nozzles D: Missing or bending occurs in 20% or more of the nozzles out of the total number of nozzles

[0079] 2.2.2. Evaluation of storage stability The ink was sealed in an aluminum pack and left at 60°C for 10 days. After leaving it, the temperature was lowered to 5°C, and 10 mL of the ink was passed through a membrane filter with a pore size of 10 μm. The membrane filter was observed after passing the ink through it, and the filter coverage was calculated. The results were evaluated according to the following criteria, and are shown in the table. A rating of "C" or higher is considered good. A: No aggregates are observed. B: The liquid was able to pass through, but aggregates were observed and the filter coverage was 10% or less. C: Liquid was able to pass through, but aggregates were observed, and the filter coverage was more than 10% and less than 30%. D: Liquid could not pass through, a large amount of aggregates was observed, and the filter coverage was 30% or more.

[0080] 2.2.3. Evaluation of washing fastness The ink compositions prepared according to the compositions of the Examples and Comparative Examples were poured into the aluminum packs of ink cartridges for the recording device, which were then installed in the recording device and filled with ink. A solid print was then performed on each color of printed textile. Pretreated cotton was used. The printed textile was then steamed for 12 minutes at 102°C under highly humidified conditions using a steamer (Matisse: Steamer DHe type). The resulting prints were then evaluated for washing fastness according to ISO 105-C10:2006. Evaluation was based on the following criteria, and the results are shown in the table. A rating of "D" or better is considered good. A: Washing fastness is grade 4 or higher. B: Washing fastness is grade 3 or higher but less than grade 4. C: Washing fastness is grade 2 or higher but less than grade 3. D: Washing fastness is grade 1 or higher but less than grade 2. E: Washing fastness is less than grade 1.

[0081] 2.3.Evaluation Results Looking at each table, the inkjet ink composition for printing contains a colorant represented by the above formula (1), a water-soluble organic solvent, and a nitrogen-containing heterocyclic compound, and the total content x (mass%) of the nitrogen-containing heterocyclic compound with respect to the total amount of the ink composition satisfies the relational expression (A) "0 < x ≤ 0.5". It was found that all the inkjet ink compositions for printing of each example have good ejection stability and washing fastness of the printed matter.

[0082] The present invention includes configurations that are substantially the same as the configurations described in the embodiments, for example, configurations having the same functions, methods, and results, or configurations having the same objectives and effects. The present invention also includes configurations in which non-essential parts of the configurations described in the embodiments are replaced. The present invention also includes configurations that exhibit the same operational effects as the configurations described in the embodiments or configurations that can achieve the same objectives. The present invention also includes configurations in which known technologies are added to the configurations described in the embodiments.

[0083] The following contents are derived from the above-described embodiments and modified examples.

[0084] The inkjet ink composition for printing a colorant represented by the following formula (1), a water-soluble organic solvent, a nitrogen-containing heterocyclic compound, and contains The total content x (mass%) of the nitrogen-containing heterocyclic compound with respect to the total amount of the ink composition satisfies the following relational expression (A). 0 < x ≤ 0.5 ···(A)

[0085]

Chemical formula

[0086] (In formula (1), a plurality of Ys are each independently a reactive group having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups, or SO2NH2 or SO3X; Xs are independently Na, K, or Li; when the number of reactive groups having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups as Y is a, the number of SO2NH2s is b, and the number of SO3Xs is c, a, b, and c satisfy the following relationship: a=1 to 2, b=0 to 2, c=1 to 3, a+b+c=4)

[0087] This inkjet textile printing ink composition contains a colorant represented by formula (1), and therefore can dye fabrics to produce images with good color development. While recorded materials formed using a colorant represented by formula (1) generally tend to have poor washing fastness, this inkjet textile printing ink composition contains a small amount of a nitrogen-containing heterocyclic compound, which improves the washing fastness of recorded materials without impairing the color development of the image. Furthermore, while the inclusion of a nitrogen-containing heterocyclic compound generally can reduce inkjet ejection stability, by limiting the content to 0.5% by mass or less, both washing fastness and ejection stability can be achieved.

[0088] In the inkjet ink composition for textile printing, The reactive group having one or more monochlorotriazine groups may have any of the structures of the following formulae (2) to (4).

[0089] [ka] ...Equation (2)

[0090] [ka] ...Equation (3)

[0091] [ka] ...Equation (4)

[0092] This inkjet ink composition for textile printing can improve the ejection stability in inkjet printing and the washing fastness of the resulting printed matter.

[0093] In the inkjet ink composition for textile printing, The nitrogen-containing heterocyclic compound may contain one or more compounds selected from the group consisting of a compound represented by the following formula (5), a 3- to 6-membered monocyclic compound, and a fused ring compound having 2 to 3 3- to 6-membered ring structures:

[0094] [ka] ...Equation (5)

[0095] (In formula (5), a plurality of Ys each independently represent a reactive group having one or more monochlorotriazine groups, SO2NH2, SO3Na, or H. When the number of reactive groups having one or more monochlorotriazine groups as Y is d, the number of SO2NH2s is e, the number of SO3Nas is f, and the number of Hs is g, d, e, f, and g satisfy the following relationship: d=1 to 2, e=0 to 2, f=1 to 3, g=1 to 3, and d+e+f+g=4.)

[0096] This inkjet ink composition for textile printing can further improve the ejection stability in inkjet printing and the washing fastness of the resulting printed matter.

[0097] In the inkjet ink composition for textile printing, The 3- to 6-membered monocyclic compound and the fused ring compound having 2 to 3 3-membered to 6-membered ring structures may have a weight average molecular weight (Mw) of 200 or less.

[0098] This inkjet ink composition for textile printing can improve the ejection stability in inkjet printing and the washing fastness of the resulting printed matter.

[0099] In the inkjet ink composition for textile printing, The nitrogen-containing heterocyclic compound may contain one or more compounds selected from the compound represented by formula (5), isoindoline, tryptamine, 2-methylpiperazine, and prolinol.

[0100] This inkjet ink composition for textile printing can improve the ejection stability in inkjet printing and the washing fastness of the resulting printed matter.

[0101] In the inkjet ink composition for textile printing, The total content x (mass %) of the nitrogen-containing heterocyclic compounds may satisfy the following relational expression: 0.01≦x (B)

[0102] This inkjet ink composition for textile printing can improve the ejection stability in inkjet printing and the washing fastness of the resulting printed matter.

Claims

1. A colorant represented by the following formula (1), a water-soluble organic solvent; a nitrogen-containing heterocyclic compound; The inkjet ink composition for textile printing, wherein the total content x (mass %) of the nitrogen-containing heterocyclic compounds relative to the total amount of the ink composition satisfies the following relational expression (A): 0<x≦0.5...(A) 【Chemistry 1】 ...Formula (1) (In formula (1), each of the plurality of Y's independently represents a reactive group having one or more groups that can be converted into a monochlorotriazine group or a vinyl sulfone group, SO ２ NH ２ , S.O. ３ X, where X is independently Na, K, or Li, and the number of reactive groups having one or more monochlorotriazine groups or groups convertible to vinyl sulfone groups as Y is determined by a, SO ２ NH ２ The number of b, SO ３ When the number of X is c, a, b, and c satisfy the following relationship: a = 1 to 2, b = 0 to 2, c = 1 to 3, a + b + c = 4)

2. In claim 1, The inkjet ink composition for textile printing, wherein the reactive group having one or more monochlorotriazine groups has any of the structures of the following formulas (2) to (4): 【Chemistry 2】 ...Formula (2) 【Transformation 3】 ...Formula (3) 【Chemistry 4】 ...Formula (4)

3. In claim 1, The inkjet ink composition for textile printing includes at least one nitrogen-containing heterocyclic compound selected from the group consisting of a compound represented by the following formula (5), a 3- to 6-membered monocyclic compound, and a fused ring compound having two or three 3- to 6-membered ring structures: 【Transformation 5】 ...Formula (5) (In formula (5), each of the plurality of Y's independently represents a reactive group having one or more monochlorotriazine groups, SO ２ NH ２ , S.O. ３ Na or H, and the number of reactive groups having one or more monochlorotriazine groups as Y is d, SO ２ NH ２ Let the number of e, SO ３ When the number of Na is f and the number of H is g, d, e, f, and g satisfy the following relationship: d = 1 to 2, e = 0 to 2, f = 1 to 3, g = 1 to 3, d + e + f + g = 4)

4. In claim 3, the 3- to 6-membered monocyclic compound and the fused ring compound having 2 to 3 3-membered to 6-membered ring structures each have a weight average molecular weight (Mw) of 200 or less.

5. In claim 3, the nitrogen-containing heterocyclic compound comprises at least one selected from the group consisting of the compound represented by formula (5), isoindoline, tryptamine, 2-methylpiperazine, and prolinol.

6. In claim 1, The inkjet ink composition for textile printing, wherein the total content x (mass %) of the nitrogen-containing heterocyclic compounds satisfies the following relational expression: 0.01≦x...(B)

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