JPH10114866A - Aqueous microdispersion of disperse dye and ink jet recording ink containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an aqueous microdispersion in which a disperse dye is effectively dispersed in the form of microparticles and which, even when it has a high solid content, is lowly viscous and stable and which is highly adaptable for a dyeing step by using a specified water-soluble addition polymer as the dispersant. SOLUTION: This dispersion comprises water a water-soluble organic solvent, a disperse dye and a dispersant which is a water-soluble addition polymer being a polymer compound synthesized from a sulfon-diol and/or an amine and a diisocyanate, having sulfonic acid groups and urethane or urea bonds and having a structure represented by any one of formulas I to V (wherein R is a residue of a sulfonic acid group-containing monomer having an alkyl, a phenyl or the like; R2 is a residue of a diisocyan ate compound; and (m) and (n) are each 1-50) and having a sulfonic acid value of 100-250. When this dispersion is used for an ink jet recording ink, the microparticles have a mean particle diameter of 250nm or below, and they are mixed with a liquid medium containing a polyhydric alcohol and/or a polyhydric alcohol monoalkyl ether.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an aqueous fine particle dispersion using a disperse dye, and more particularly, to an aqueous fine particle dispersion useful as a textile dyeing liquid or an ink jet printing ink. The present invention uses a disperse dye and has a fine particle state having a particle size distribution in the range of 10 to 2,000 nm, and is particularly stable even in a fine particle state having an average particle diameter of 250 nm or less which is optimal for an ink for inkjet recording. The present invention relates to an aqueous fine particle dispersion having improved dispersibility, and an ink jet recording ink using the same.

[0002]

2. Description of the Related Art In recent years, a system for performing plateless printing using an ink jet recording method has been proposed. The dispersion used in this method is in a fine particle state having an average particle diameter of 250 nm or less, and has a viscosity of 3 centipoise or less even at a solid content of about 10%, as basic requirements required by the inkjet system itself. Is required to be a low-viscosity, stable, fine-particle dispersion.

On the other hand, a technique for dispersing a disperse dye in an aqueous medium has been conventionally known. First, typical dispersants for aqueous dispersion of disperse dyes include, for example,
Formalin condensates of naphthalene sulfonic acid, lignin sulfonic acid and the like can be mentioned, and examples of the surfactant include JP-A-48-14888 (Hoechst) and JP-A-50-88.
100386 (Nichika Chemical), JP-A-54-248
No. 4 (Toho Kagaku), Japanese Unexamined Patent Publication No. 55-54353 (ICI), and the like are known. These techniques are all used in the dispersion method which is industrially performed in the existing dyeing method. However, these conventional material technologies cannot efficiently and stably obtain a fine particle dispersion having an average particle diameter of 250 nm or less. This is because such a level of micronization was not required in the conventional printing method.

On the other hand, a technique for dispersing fine particles of a pigment in an aqueous medium has been put to practical use in the fields of inks for writing implements, inks for ink jet recording, photoresists, and liquid developers for electrophotography. However, these technologies and materials
Even when applied to the dispersion of fine particles in the submicron region of a disperse dye, the desired results are hardly obtained. Although the chemical reason is not clear, the present inventors presume that the disperse dye is more hydrophobic than the pigment and difficult to treat particles for aqueous dispersion. It is considered that the first cause is that the wetting of the particle surface and the disintegration into small particles, which are the initial processes, are difficult to proceed.

[0005] According to the dispersant and dispersion method currently used in aqueous pigment dispersion, very stable dispersions have been produced, and these dispersions are used as inks and paints. When an image is formed by printing or coating, water resistance, abrasion resistance and the like are developed, and an excellent image is formed. This is presumably because the dispersant is strongly adsorbed on the pigment particles as a protective colloid. However, it is not easy to chemically or physically desorb the substance once adsorbed. This contradicts the requirement that the dispersant must be removed after dyeing in the fabric dyeing process. Furthermore, it is important to disperse the particles in a stable and fine particle size state and to impart stable suitability to the fabric dyeing step. However, with the above-mentioned conventional materials, it has been extremely difficult to obtain a dispersion with high yield and high stability.

[0006]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a method for dispersing dyes in which fine particles are efficiently dispersed in a state in which the average particle diameter is 250 nm or less based on the above background. An object of the present invention is to provide a fine particle dispersion which has a low viscosity even when a dispersion having a high solid content is used, and which can maintain the above-mentioned dispersion state stably for a long period of time. Further, an important object of the present invention is to provide a fine particle dispersion imparted with sufficient suitability for a dyeing step, such as reducing washing properties and cotton stainability after dyeing, and an ink jet recording ink using the same. To provide.

[0007]

The above object is achieved by the present invention described below. That is, the present invention provides an aqueous fine particle dispersion containing at least water, a water-soluble organic solvent, a disperse dye and a dispersant, wherein the dispersant is a sulfone obtained from a diol and / or amine having a sulfone group and a diisocyanate. A water-based fine particle dispersion of a disperse dye, which is a water-soluble addition polymer having an acid group and a urethane bond or a urea bond, and a polyhydric alcohol and / or a monoalkyl ether of a polyhydric alcohol, Is an ink for inkjet recording having at least

[0008] The aqueous fine particle dispersion of the disperse dye of the present invention having the above-mentioned structure has a high hydrophobicity and a specific water-soluble property capable of exhibiting an effective dispersibility with respect to a disperse dye which is a water-insoluble coloring material. Since the addition polymer is used as a dispersing agent for the disperse dye, the disperse dye is finely dispersed in a desired particle size, and has a low viscosity even when the solid content is set to a high level, and becomes a stable dispersion for a long period of time. Further, the aqueous fine particle dispersion in the present invention is applied to an ink to form an aqueous fine particle dispersed ink, thereby fabric, recording paper having an absorbability of the aqueous ink, inkjet paper, film, for improving printability. It is possible to provide an ink that gives a recorded image with high color quality and excellent fastness to a metal, a plastic, or the like that has been subjected to a base treatment. That is, when the aqueous fine particle dispersion of the present invention is applied to ink, it is necessary to perform recording on the above-described various types of recording media, and good particle dispersibility in the submicron region, storage stability, and inkjet recording. The apparatus has excellent discharge characteristics and the like.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. First, the substance used in the present invention will be described. (Water-soluble addition polymer) The water-soluble addition polymer used as a dispersant in the present invention is shown below with examples of basic raw materials and their structures. It is a polymer compound having a sulfonic acid group and a urethane bond or a urea bond synthesized from isocyanate.

The basic structure of the water-soluble addition polymer in the present invention is shown below by taking diisocyanate (a) and diol (b) or amine (c) having one sulfone group as an example.

Embedded image (In the above formulas (a) to (e), R represents a residue of a sulfonic acid group-containing monomer having any one of an alkyl group, a phenyl group, and a naphthalene group. R ₂ represents a residue of a diisocyanate compound. Wherein n represents an integer of any of 1 to 50, and m represents an integer of any of 1 to 50.

The structure as described above is similar in structure to a conventionally used formalin condensate of naphthalenesulfonic acid and the like. However, in the above-described polymer compound, the dispersibility of the polymer compound in a disperse dye is significantly different from that of a formalin condensate or the like, because the atomic group connecting the repeating units has a urethane bond or a urea bond. It is because the strong hydrogen bonding force of these linking groups interacts with the polar group of the dye, so that the dispersion of the fine particles and the stability of the dispersed fine particles (prevention of agglomeration of fine particles and detachable dispersing agent) It is considered that they are contributing.

In the present invention, in particular, a sulfonic acid value of 10 which is produced from a diol having a sulfone group or an amino compound having a sulfone group and a diisocyanate is used.
An excellent effect is obtained when a water-soluble addition polymer having a sulfone group of from 0 to 250, in which the average particle size of the aqueous fine particle dispersion is adjusted to 250 nm or less, is used as an inkjet ink. . That is, when the sulfonic acid is introduced in the sulfonic acid value range of 100 to 250, favorable dispersibility and suitability for the dyeing step can be obtained. The acid value of the water-soluble addition polymer used as a dispersant in the present invention, the size of the skeletal structure, the number of sulfonic acids,
It can be appropriately changed depending on the skeleton of the isocyanate or the amount of the diol having no sulfonic acid used in combination.

[0013] The aqueous fine particle dispersion of the disperse dye of the present invention having the above-mentioned specific dispersant can be used as an ink jet recording ink, particularly, when forming an image on a cloth. The ink composition is preferably 50 to 90% by weight of water, 1 to 15% by weight of an aqueous fine particle dispersion of a disperse dye, and 5 to 40% by weight of a polyhydric alcohol. And / or a monohydric ether of a polyhydric alcohol.

Hereinafter, the aqueous fine particle dispersion of the disperse dye of the present invention and the constituent materials of an ink jet recording ink having the same will be described in detail with reference to specific examples.
The aqueous fine particle dispersion of the disperse dye of the present invention has a water-soluble property having a sulfonic acid group obtained from a diol having a sulfone group and / or an amine having a sulfone group and a diisocyanate and a urethane bond or a urea bond as a dispersant. Although an addition polymer is used, in the present invention, a diol having a sulfone group represented by the following formula (F
It is preferable to use 1) to (F7). Of course, the compounds listed below are examples, and the present invention is not limited thereto.

[0015]

Embedded image (F1) N, N-Bis (2-hydroxyethyl) -2-aminoeth
ane sulfonic acid

Embedded image (F2) 3- [N, N-Bis (2-hydroxyethyl) amino] -2-
hydroxypropane sulfonic acid

Embedded image (F3) 2,3-Dihydroxynaphthalene-6-sulfoni
c acid monosodium salt

(F4) 1,8-Dihydroxynaphthalene-3,6-disul
fonic acid disodium salt

(F5) 2,7-Dihydroxynaphthalene-3,6-disul
fonic acid disodium salt

[0016]

(F6) 1,7-Dihydroxynaphthalene-3-sulfoni
c acid monosodium salt

Embedded image (F7) (In the above formula, M represents a hydrogen atom or an alkali metal. R ₁ and R ₂ are each independently —CH ₂ , —CH ₂ C
_{H 2, -CH 2 CH 2 CH} 2, -CH 2 NH, -CH 2 CH 2 N
H (where the bond represented by-is OH
Is the base bond). R ₃ represents —CH ₂ , —CH ₂ CH
₂ represents one of the -CH ₂ NH (where - bond indicated by represents a bond SO ₃ M group side). However, R ₃ may not be present. )

Examples of the amino compound having a sulfone group preferably used in the present invention include compounds (F8) to (F10) represented by the following formulas.

(F8) (In the above formula, M represents a hydrogen atom or an alkali metal, and R ₁ represents any _one of —CH ₂ , —CH ₂ CH _{2, and} —CH ₂ NH (provided that the bond represented by — is SO ₃ M A bond on the base side), provided that R ₁ may not be present.)

[0018]

(F9)

(F10)

The water-soluble addition polymer used as a dispersant in the present invention is obtained by reacting the above-mentioned sulfonated diol and / or sulfonated diamine with diisocyanate. The diisocyanates that can be used include the following. Basically, bifunctional 2,4-tolylene diisocyanate,
2,6-tolylene diisocyanate, hexamethylene diisocyanate, m-phenylene diisocyanate, p
-Phenylene diisocyanate, 4,4'-diphenylmethane diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, lysine diisocyanate And naphthalene, trimethylhexamethylene diisocyanate, 3,3′-dichloro-4,4′-biphenylenediisocyanate, 1,5-naphthalenediisocyanate, 1,5-tetrahydronaphthalenediisocyanate and the like.

Further, a compound having three or more isocyanate groups such as an adduct of hexamethylene diisocyanate, a modified form of urethane, a modified form of allophanate, a modified form of buret, or a modified form of isocyanurate may be obtained by adding a compound having three or more isocyanate groups to the resulting aqueous solution. It is also possible to use a small amount for the purpose of imparting a branched structure to the urethane polymer as required.

In obtaining the water-soluble addition polymer used in the present invention, it is possible to use a diol having no sulfone group together with a diol having a sulfone group. By using a diol having no sulfone group in combination, the degree of sulfonation and the degree of freedom of the molecular chain of the obtained water-soluble addition polymer can be controlled. Examples of the diols having no sulfone group include ethylene glycol, diethylene glycol, triethylene glycol, tripropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol propylene glycol, and butylene glycol. , Polyethylene glycol 300, thiodiglycol, and the like, but are not limited thereto.

Using the above-mentioned raw materials, a water-soluble addition polymer having a sulfonic acid group and a urethane bond or a urea bond, which is a dispersant for the aqueous fine particle dispersion of the disperse dye of the present invention, is produced. The production method and specific examples of the water-soluble addition polymer which can be preferably used in the present invention are described below. Compounds synthesized from sulfone group-containing diols or sulfone group-containing amines are synthesized by the following procedure. A diol compound or amine having a sulfone group is neutralized with a base such as sodium, lithium, ammonia, alcoholamine, or alkylamine, and NMP or ME
It dissolves in polar solvents such as K. While maintaining the solution at a low temperature of 50 ° C. or lower, the reaction is carried out while the diisocyanate compound dissolved in the same solvent is added dropwise. When the reaction is completed, the solution is neutralized by adding a basic aqueous solution. Further, while removing the volatile organic solvent from the solution under reduced pressure, the solution is converted to an aqueous solvent while supplementing water and a base.

The water-soluble addition polymer (SU-1) which can be preferably used in the present invention, which is synthesized from a sulfone group-containing diol or a sulfone group-containing amine and a diisocyanate as described above. To (SU-8), a sulfonic acid value, and a number average molecular weight. (SU-1)

Embedded image The compound having the above-mentioned structure is the same as isoferon diisocyanate and N, N-Bis (2-hydrox
yethyl) -2-aminoethane sulfonic acid. A compound having a polymerization degree n of about 20 was obtained, and the compound was designated as SU-1. The SU-1 compound had a sulfonic acid value of 140 and a molecular weight of about 9,500.

(SU-2)

Embedded image The compound having the above structure is hexamethylene diisocyanate and N, N-Bis (2-hydr) described above as (F1).
Obtained from (oxyethyl) -2-aminoethane sulfonic acid. Among the above compounds, those having a sulfonic acid value of 160 and a molecular weight of about 7,500 were designated as SU-2.

(SU-3)

Embedded image The compound having the above structure is hexamethylene diisocyanate and 2,3-dihydroxyn mentioned above as (F3).
Obtained from aphthalene-6-sulfonic acid monosodium salt. Among the above compounds, those having a sulfonic acid value of 130 and a molecular weight of about 8,000 were designated as SU-3.

(SU-4)

Embedded image The compound having the above structure is isoferon diisocyanate and 1,8-dihydroxynap as previously described as (F4).
hthalene-3,6-disulfonic acid disodium salt. Among the above compounds, those having a sulfonic acid value of 190 and a molecular weight of about 6,500 were designated as SU-4.

(SU-5)

Embedded image The compound having the above structure is a polyurethanediol compound (molecular weight: about 1,200) obtained from ethylene glycol and hexamethylene diisocyanate, and 2,7-dihydroxynaphthalene-3,6- mentioned above as (F5). d
It is obtained by using two diols of isulfonic acid disodium salt in a weight ratio of 1: 2 and using hexamethylene diisocyanate as a diisocyanate. Of the above compounds, a sulfonic acid value of 150 and a molecular weight of about 9,500
Was designated as SU-5.

(SU-6)

Embedded image The compound having the above structure is a water-soluble compound having a urea bond in the molecule obtained from 2 mol of trimethylhexamethylene diisocyanate and 1 mol of sulfamic acid (belonging to the above-mentioned amino compound (F8)). is there. The sulfonic acid value of the compound (SU-6) is 200, and the molecular weight is about 556.

(SU-7)

Embedded image The compound having the above structure is a water-soluble compound having a urea bond in the molecule obtained from 2 mol of hexamethylene diisocyanate and 1 mol of the compound (belonging to the above-mentioned compound amino (F9)). The compound (SU-
The sulfonic acid value of 7) is 323 and the molecular weight is 692.

(SU-8)

Embedded image The compound having the above structure is a water-soluble compound having a urea bond in the molecule obtained from 2 mol of hexamethylene diisocyanate and 1 mol of the compound (belonging to the above-mentioned amino compound (F10)). The compound (SU-
8) The sulfonic acid value is 323 and the molecular weight is 692.

(Disperse Dye) In the aqueous fine particle dispersion of the disperse dye of the present invention, examples of the disperse dye dispersed by the water-soluble addition polymer having the above constitution include the following dyes. -Yellow disperse dye CIDisperse Yellow 5, CIDisperse Yellow 42,
CIDisperse Yellow54, CIDisperse Yellow 6
4, CIDisperse Yellow 79, CIDisperse Yellow
82, CIDisperse Yellow 83, CIDisperse Yello
w 93, CIDisperse Yellow 99, CIDisperse Yel
low 100, CIDisperse Yellow 119, CIDisper
se Yellow 122, CI Disperse Yellow 124, CI
Disperse Yellow 126, CIDisperse Yellow 16
0, CIDisperse Yellow 184: 1, CIDisperse Y
ellow 186, CIDisperse Yellow 198, CIDisp
erse Yellow 199, CIDisperse Yellow 204, C.
I. Disperse Yellow 224, CIDisperse Yellow 23
7,

Orange disperse dye CIDisperse Orange 13, CIDisperse Orange 2
9, CIDisperse Orange 31: 1, CIDisperse Ora
nge 33, CIDisperse Orange 49, CIDisperse O
range 54, CIDisperse Orange 55, CIDisperse
Orange 66, CIDisperse Orange 73, CIDisper
se Orange 118, CI Disperse Orange 119, CID
isperse Orange 163,

Red disperse dye CI Disperse Red 54, CI Disperse Red 72, CI
Disperse Red 73, CIDisperse Red 86, CIDisp
erse Red 88, CIDisperse Red 91, CIDisperse
Red 92, CIDisperse Red 93, CIDisperse Red
111, CIDisperse Red 126, CIDisperse Red
127, CIDisperse Red 134, CIDisperse Red
135, CIDisperse Red 143, CIDisperse Red
145, CIDisperse Red 152, CIDisperse Red
153, CIDisperse Red 154, CIDisperse Red
159, CIDisperse Red 164, CIDisperse Red
167: 1, CIDisperse Red 177, CIDisperse
Red 181, CIDisperse Red 204, CIDisperse
Red 206, CIDisperse Red 207, CIDisperse
Red 221, CIDisperse Red 239, CIDisperse
Red 240, CIDisperse Red 258, CIDisperse
Red 277, CIDisperse Red 278, CIDisperse
Red 283, CIDisperse Red 311, CIDisperse
Red 323, CIDisperse Red 343, CIDisperse
Red 348, CIDisperse Red 356, CIDisperse R
ed 362,

A purple disperse dye C.I.Disperse Violet 33;

Blue disperse dyes CI Disperse Blue 56, CI Disperse Blue 60, C.I.
I. Disperse Blue 73, CI Disperse Blue 87, CI
Disperse Blue 113, CIDisperse Blue 128, C.I.
I. Disperse Blue 143, CIDisperse Blue 148,
CIDisperse Blue 154, CIDisperse Blue 15
8, CIDisperse Blue 165, CIDisperse Blue 1
65: 1, CIDisperse Blue 165: 2, CIDisper
se Blue 176, CIDisperse Blue 183, CIDisp
erse Blue 185, CIDisperse Blue 197, CIDi
sperse Blue 198, CI Disperse Blue 201, CI
Disperse Blue 214, CI Disperse Blue 224, C.I.
I. Disperse Blue 225, CIDisperse Blue 257,
CIDisperse Blue 266, CIDisperse Blue 26
7, CIDisperse Blue 287, CIDisperse Blue 3
54, CIDisperse Blue 358, CIDisperse Blue
365, CIDisperse Blue 368,

Green disperse dye C.I.Disperse Green 6: 1, C.I.Disperse Green 9

Among the above dyes, more preferred dyes are as follows. -Yellow disperse dye CIDisperse Yellow 5, CIDisperse Yellow 42,
CIDisperse Yellow83, CIDisperse Yellow 9
3, CIDisperse Yellow 99, CIDisperse Yellow
198, CIDisperse Yellow 224 ・ Orange disperse dye CIDisperse Orange 29, CIDisperse Orange 4
9. CIDisperse Orange 73

Red disperse dye CI Disperse Red 92, CI Disperse Red 126, C.I.
I. Disperse Red 145, CI Disperse Red 152, C.
I. Disperse Red 159, CI Disperse Red 177, C.
I. Disperse Red 181, CIDisperse Red 206, C.I.
I. Disperse Red 283-Blue disperse dye CI Disperse Blue 60, CI Disperse Blue 87, C.I.
I. Disperse Blue 128, CIDisperse Blue 154,
CIDisperse Blue 201, CIDisperse Blue 21
4, CIDisperse Blue 224, CIDisperse Blue 2
57, CIDisperse Blue 287, CIDisperse Blue
368

The dyes described above are preferred examples that can be used in the present invention, and the present invention is not limited to the dyes described above, and may be, of course, newly synthesized dyes. . In particular, in the present invention, it is preferable to use a disperse dye product taken out in the form of a wet cake during the production of the dye, since good fine particle dispersion can be achieved. That is, when the product in such a wet cake state is used in the dispersion treatment step, the dispersion can be efficiently made into fine particles. However, the use of a product taken out in the form of a wet cake is basically not a problem of work efficiency and has little effect on the attainable performance, and is not an essential condition in the present invention.

(Production of Dispersion) The aqueous fine particle dispersion of the disperse dye of the present invention can be obtained by subjecting the above-mentioned disperse dye to a dispersion treatment with the above-mentioned water-soluble addition polymer. At the time of dispersion, the disperse dye and the water-soluble addition polymer are mixed in a weight ratio of 10
After mixing in the range of 0:30 to 100: 200 and premixing, the mixture is dispersed. As a method of the dispersion treatment, glass beads having a particle size in the range of 0.5 to 2.0 mm, silica-alumina ceramic beads, zirconia beads, and a dispersion method using natural silica beads such as Ottawa sand as a medium. It is preferably used.

The dispersing machine used in the dispersion of the present invention may be any commonly used dispersing machine as long as the average particle size of the disperse dye in the obtained dispersion is efficiently within a desired range. Any device such as a device may be used. For example, a ball mill, a sand mill and the like can be mentioned. Among them, a high-speed sand mill is preferable, and examples thereof include a super mill, a sand glider, a bead mill, an agitator mill, a Glen mill, a Dyno mill, a pearl mill, and a Kobol mill (all trade names). In addition, a roll mill, a jet mill, or the like, which does not use beads but can apply a high shear stress, is also effective to be used in combination, since impurities are less mixed therein.

The aqueous fine particle dispersion of the disperse dye of the present invention comprises
In order to be suitable when used as a constituent material of an ink-jet ink, those having an average particle size of 250 nm or less are preferable. That is, when the average particle size is larger than 250 nm,
When used for applications such as ink for inkjet recording,
Poor discharge performance causes clogging, and it is difficult to obtain a fine high-quality image. However, if the water-soluble addition polymer or the dispersion method used in the present invention is used, a stable dispersion can be efficiently obtained, and the particle size distribution of the obtained disperse dye is in the range of 10 to 2,000 nm. Is possible. Therefore, it is also possible to prepare a dispersion having a particle size distribution according to other uses, not limited to the above-described inkjet ink, to obtain a dispersion suitably used for ordinary dyeing and the like.

In the present invention, as a method of obtaining a dispersion having a desired particle size distribution, for example, a method of reducing the size of a pulverizing medium of a dispersing machine, a method of dispersing and then classifying by pressure filtration or centrifugation, Techniques such as aging treatment and pressure filtration are mentioned. In the present invention, a dispersion having a desired particle size distribution can be easily obtained by these techniques. For example, coarse particles can be removed by centrifugation, but in the present invention, since a water-soluble urethane polymer is used as a dispersant, fine particles can be efficiently formed. The desired dispersion can be obtained under low centrifugation conditions without producing any matter. As described above, the aqueous fine particle dispersion of the present invention is produced.

Next, the ink jet recording ink of the present invention comprising at least the aqueous fine particle dispersion of the present invention having the above-mentioned structure and a polyhydric alcohol and / or a monoalkyl ether of a polyhydric alcohol. Will be described. The ink for inkjet recording of the present invention is produced by adjusting the aqueous fine particle dispersion of the present invention to a liquid medium configuration according to the purpose of use. Therefore, first, the liquid medium used in this case will be described. Examples of the liquid medium that can be used in the present invention include water-miscible humectants such as monohydric alcohols, polyhydric alcohols, and monoalkyl ethers of polyhydric alcohols, which are usually used in aqueous fine particle dispersions. The water-miscible humectants can be classified into the following three groups as a result of classification by the present inventors based on the functions possessed by them. Specific solvents belonging to these groups are listed below. Group 1: Solvents that have high moisture retention, are difficult to evaporate, and are excellent in hydrophilicity. Group 2: Solvents having a hydrophobic atom group at the end and having good wettability to a hydrophobic surface and also having evaporation and drying properties. : Moderate wettability, low viscosity solvent (monohydric alcohols)

Therefore, it is preferable that the liquid medium used in the ink jet recording ink of the present invention is appropriately selected from these based on the function of these solvents and used in combination as the liquid medium. In particular, in the present invention, it is preferable to use a liquid medium having at least a polyhydric alcohol and / or a monoalkyl ether of a polyhydric alcohol. In the inkjet recording ink of the present invention, the total amount of the liquid medium comprising the water-soluble solvent as described above is generally in the range of 5 to 40% by weight based on the entire aqueous fine particle dispersion of the disperse dye of the present invention. Is preferred. 5
If the amount is less than 40% by weight, problems such as poor ink ejection properties and clogging may occur. In particular, the preferred composition of the ink jet recording ink of the present invention that can be used when forming an image on a cloth is 50 to 90% by weight of water, 1 to 15% by weight of an aqueous fine particle dispersion of a disperse dye, And at least 5 to 40% by weight of a polyhydric alcohol and / or a monoalkyl ether of a polyhydric alcohol.

The solvents belonging to the first group include, specifically, ethylene glycol, diethylene glycol, triethylene glycol, tripropylene glycol, glycerin, 1,2,4-butanetriol, 1,2,6-
Hexanetriol, 1,2,5-pentanetriol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, dimethylsulfoxide,
Diacetone alcohol, glycerin monoallyl ether, propylene glycol, butylene glycol, polyethylene glycol 300, thiodiglycol, N-methyl-2-pyrrolidone, 2-pyrrolidone, γ-butyrolactone, 1,3-dimethyl-2-imidazolidinone , Sulfolane, trimethylolpropane, trimethylolethane, neopentyl glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoallyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol Monomethyl ether, triethylene glycol monoethyl ether, propylene glycol Glycol monomethyl ether, dipropylene glycol monomethyl ether, bis β- hydroxyethyl sulfone, bis β- hydroxyethyl urea, urea, acetonyl acetone, pentaerythritol, and 1,4-cyclohexane diol.

Examples of the solvents belonging to the second group include hexylene glycol, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monophenyl ether, diethylene glycol diethyl ether, and diethylene glycol monobutyl ether. Butyl ether, diethylene glycol monoisobutyl ether, triethylene glycol monobutyl ether,
Triethylene glycol dimethyl ether, triethylene glycol diethyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol diethyl ether, propylene glycol monobutyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, tripropylene glycol Monomethyl ether, glycerin monoacetate, glycerin diacetate, glycerin triacetate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, cyclohexanol, 1,2-cyclohexanediol, 1-butanol, 3-methyl-1,5-pentanediol, 3-Hexe 2,5-diol, 2,3
Butanediol, 1,5-pentanediol, 2,4-
Pentanediol, 2,5-hexanediol and the like can be mentioned.

The solvents belonging to the third group are components that can be optionally used in the ink of the present invention. Specific examples include ethanol, n-propanol, 2-propanol, 1-methoxy-2-propanol, furfuryl alcohol, tetrahydrofurfuryl alcohol and the like.

When the aqueous fine particle dispersion of the disperse dye of the present invention is mixed with the above-mentioned liquid medium comprising a polyhydric alcohol or the like to prepare an ink for ink jet recording, the p
It is preferable to adjust H to a neutral to basic region. Specifically, the pH of the ink is 5 to 10, preferably 7 to 9
Is desirably within the range. By adjusting the pH to this range, the storage stability of the ink can be obtained. Furthermore, especially when an image is formed on a fabric, the fabric is suitable for dyeing properties, reducing washing after dyeing, washing with water, and the like. Is obtained.

Examples of the pH adjusting agent for the base species used at this time include inorganic bases such as sodium hydroxide, potassium hydroxide and lithium hydroxide, ethanolamine, diethanolamine, triethanolamine and N-methylethanolamine. , N-ethyldiethanolamine, 2-amino-2-methylpropanol, 2-ethyl-2-amino-1,3-propanediol, 2- (2-aminoethyl) ethanolamine, tris (hydroxymethyl) aminomethane, ammonia And organic bases such as glycine, glycylglycine, histidine, L-lysine, L-arginine, piperidine, morpholine and β-dihydroxyethylurea. Incidentally, these substances are used when preparing a water-based fine particle dispersion of the disperse dye of the present invention, when converting a solvent from an organic solvent to an aqueous solvent at the time of synthesizing a specific water-soluble addition polymer used as a dispersant. Can also be used as a neutralizing agent.

Further, when the aqueous fine particle dispersion of the disperse dye of the present invention is applied to an ink for ink jet recording, etc., the dyeing property is imparted to the cloth and the discharge efficiency is improved when the ink is used in a bubble jet type ink jet apparatus. For purposes, it may be practically advantageous to add a surfactant. Examples of the surfactant used in this case include nonionic surfactants such as formalin condensate of naphthalenesulfonic acid and polyoxyethylene long-chain alkyl ether; anionic dissociation selected from polyoxyethylene phosphoric acid and carboxylic acid. A nonionic anionic surfactant such as a polyoxyethylene alkyl ether having a group at the ethylene oxide terminal and having an HLB of 10 or more, or a polyoxyethylene alkyl phenyl ether is used.
The addition of these surfactants in the present invention is preferably appropriately selected and added as necessary in consideration of foaming properties.

When the aqueous fine particle dispersion of the disperse dye of the present invention is used as an ink jet recording ink for dyeing, additives such as a preservative and an antifoaming agent may be required. It is preferable that these additives are appropriately selected from water-soluble preservatives, defoamers having good miscibility with water, and the like.

[0053]

Next, the present invention will be described in detail with reference to inks for inkjet recording in Examples. In the following description, "parts" and "%" are based on weight unless otherwise specified. Example 1 Dispersion DBL-1 of Example 1 was prepared by the following method using SU-1 obtained from the above-mentioned diol having a sulfone group and diisocyanate.
Inkjet recording ink BL- using BL-1
1 was produced. Table 1 summarizes the raw materials, sulfonic acid values, and average molecular weights of the water-soluble addition polymers used in the examples, and the compositions of the dispersions and ink-jet recording inks in each example obtained using these. Are shown in Table 2.

(Dispersion DBL-1) SU-1 (monoethanolamine neutralized 50% aqueous solution, pH 8.0) 10 parts I. Disperse Blue 60 Wet cake prototype (solid content 40%) 60 parts (solid content) ・ Ethylene glycol 10 parts ・ Water 130 parts The above materials were charged in a batch type vertical sand mill, and after premixing for 30 minutes, 1 mm Filled with zirconium beads having a diameter of 2,000 r while cooling with water
Dispersion treatment was performed at pm for 5 hours. The viscosity of the liquid after dispersion was 5 cps. This dispersion is prepared at 5,000 rpm for 2 hours.
The mixture was centrifuged at 0 minutes to remove coarse particles, the solid content was 11.0%, the average particle diameter was 160 nm, and the surface tension was 48 dyn.
/ Cm, pH 7.5 dispersion DBL-1 was obtained.

(Ink for inkjet recording BL-1) Dispersion DBL-1 50 parts Diethylene glycol 20 parts Isopropyl alcohol 3 parts Water 27 parts Lithium hydroxide aqueous solution (pH adjustment) Some amount The above components are mixed well. Then, the mixture was filtered under pressure using a 0.25 μm membrane filter to prepare a blue inkjet recording ink BL-1 having a viscosity of 2.5 cps, a surface tension of 45 dyn / cm, and a pH of 9.0.

Example 2 Using SU-2 obtained from the above-mentioned diol having a sulfone group and diisocyanate, the dispersion DBL-2 of Example 2 and the ink for ink-jet recording were prepared in the following manner. BL-2 and BL-3 were produced. (Dispersion DBL-2) 15 parts of SU-2 (50% aqueous solution of sodium hydroxide neutralized, pH 9.0) I. Disperse Blue 154 Wet cake prototype (solid content 40%) 50 parts (solid content) ・ Ethylene glycol 10 parts ・ Water 120 parts The above materials were charged in a batch type vertical sand mill, and after premixing for 30 minutes, 1 mm Glass beads of a diameter were filled as a medium, and a dispersion treatment was performed at 2,000 rpm for 5 hours while cooling with water. The viscosity of the liquid after dispersion is 6.0.
cps. This dispersion is treated at 8,000 rpm for 20 minutes.
For 1 minute to remove coarse particles.
2%, average particle size 130 nm, surface tension 50 dyn / c
m, pH 8.3 Dispersion DBL-2 was obtained.

(Ink for Inkjet Recording BL-2) Dispersion DBL-2 30 parts Ethylene glycol 10 parts Glycerin 10 parts Water 50 parts Monoethanolamine A little amount The above components are mixed well, and 0.25 μm The mixture was filtered under pressure using a membrane filter of the formula (1) to prepare a blue inkjet recording ink BL-2 having a viscosity of 2.3 cps, a surface tension of 47 dyn / cm and a pH of 9.3.

(Ink for ink jet recording BL-3) Dispersion DBL-2 40 parts Ethylene glycol 10 parts Glycerin 10 parts Polyoxyethylene nonylphenyl ether (HLB = 12) 0.3 part Water 36 parts 0.2% citric acid trisodium salt The above components are mixed well, filtered under pressure using a 0.25 μm membrane filter, and printed with a blue inkjet ink having a viscosity of 2.2 cps, a surface tension of 37 dyn / cm, and a pH of 8.6. Ink BL-2 was prepared.

Example 3 Using SU-3 obtained from the above-mentioned diol having a sulfone group and diisocyanate, the dispersion DY-1 of Example 3 and an ink for inkjet recording were prepared in the following manner. Ink DY-1 was produced. (Dispersion DY-1) 20 parts of SU-3 (47.5% aqueous solution of lithium hydroxide neutralized, pH 9.0) I. Disperse Yellow 83 Wet cake prototype (solid content 30%) 90 parts (solid content) ・ Ethylene glycol 10 parts ・ Water 80 parts Using the above materials, dispersion treatment was conducted in substantially the same manner as in Example 1, and the viscosity was 6 A dispersion of 0.5 cps was prepared. The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 15%, an average particle diameter of 135 nm, and a surface tension of 4%.
A dispersion DY-1 having 6 dyn / cm and a pH of 8.5 was prepared.

(Inkjet recording ink DY-1) Dispersion DY-1 30 parts Diethylene glycol 15 parts N-methylpyrrolidone 10 parts Water 45 parts Lithium hydroxide aqueous solution The solution was filtered under pressure using a 0.25 μm membrane filter to prepare a yellow inkjet recording ink DY-1 having a viscosity of 2.6 cps, a surface tension of 44 dyn / cm, and a pH of 9.6.

Example 4 Using SU-4 obtained from the above-mentioned diol having a sulfone group and diisocyanate, the dispersion DBk-1 of Example 4 and the ink for ink-jet recording were prepared in the following manner. DBk-1 and DBk-2 were produced. (Dispersion DBk-1) 13 parts of SU-4 (monoethanolamine neutralized 45% aqueous solution, pH 7.3) 13 parts 12 parts of CI Disperse Orange 13 powder 1 part of CI Disperse Red 152 powder 5 parts of CI Disperse Blue 183 powder 5 Parts-CIDisperse Blue 264 powder 6 parts-ethylene glycol 10 parts-water 135 parts-defoamer Surfynol 104E (manufactured by Nissin Chemical Co., Ltd.) a little amount Using the above materials, dispersion treatment is performed in substantially the same manner as in Example 1. Was performed to prepare a dispersion having a viscosity of 5.0 cps. The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 13%, an average particle size of 175 nm, and a surface tension of 4%.
A dispersion DBk-1 having 2 dyn / cm and a pH of 7.0 was prepared.

(Ink for Inkjet Recording DBk-1) 55 parts of dispersion DBk-1 20 parts of bis 2-hydroxyethyl sulfone 5 parts of thiodicrycol 5 parts of water 20 parts of monoethanolamine The mixture was filtered under pressure using a 0.25 μm membrane filter to prepare a black ink jet recording ink DBk-1 having a viscosity of 2.9 cps, a surface tension of 40 dyn / cm, and a pH of 8.5.

(Ink for ink jet recording DBk-2) 55 parts of dispersion DBk-1 20 parts of bis 2-hydroxyethyl sulfone 5 parts of thiodiglycol 5 parts of sodium lauryl sulfate 0.5 part of water 19.5 parts of water Monoethanolamine Slight amount These components were mixed well, filtered under pressure using a 0.25 μm membrane filter, and had a viscosity of 2.8 cps, a surface tension of 38 dyn / cm, and a pH of 8.5. 2 was produced.

Example 5 Using SU-5 obtained from the above-mentioned diol having a sulfone group and diisocyanate, the dispersion DR-1 of Example 5 and an ink for inkjet recording were prepared in the following manner. Ink DR-1 was produced. (Dispersion DR-1) SU-5 (monoethanolamine neutralized 45% aqueous solution, pH 7.2) 20 parts C.I. I. Disperse Red 92 powder 25 parts ・ Ethylene glycol 10 parts ・ Defoaming agent Surfynol 104E (manufactured by Nissin Chemical) Some amount (<1 part) ・ Water 145 parts Using the above materials, it is almost the same as in Example 1. To perform a dispersion treatment to prepare a dispersion having a viscosity of 5.3 cps. The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 13%, an average particle diameter of 140 nm, and a surface tension of 4%.
A dispersion DR-1 of 2 dyn / cm, pH 7.0 was prepared.

(Inkjet recording ink DR-1) 35 parts of dispersion DR-1 10 parts of thiodiglycol 15 parts of triethylene glycol 5 parts of urea 35 parts of water A little amount of aqueous lithium hydroxide solution The above components Was mixed well and filtered under pressure using a 0.25 μm membrane filter to prepare a red inkjet recording ink DR-1 having a viscosity of 2.5 cps, a surface tension of 40 dyn / cm and a pH of 8.8.

Example 6 Using SU-6 obtained from the above-mentioned amine having a sulfone group and diisocyanate, the following method was used.
A dispersion DR-2 of Example 6 and an ink DR-2 for inkjet recording were produced. (Dispersion DR-2) 12 parts of SU-6 (50% aqueous solution of lithium hydroxide neutralized, pH 7.5) I. Disperse Red 152 Powder 25 parts ・ Ethylene glycol 10 parts ・ Water 150 parts ・ Ethanol 5 parts Using the above materials, a dispersion treatment was performed in substantially the same manner as in Example 1 to prepare a dispersion having a viscosity of 6.8 cps. . The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 12%, an average particle diameter of 152 nm, and a surface tension of 4%.
A dispersion DR-2 of 5 dyn / cm, pH 7.3 was prepared.

(Inkjet recording ink DR-2) 45 parts of dispersion DR-2 15 parts of ethylene glycol 10 parts of glycerin 6 parts of triethylene glycol mono n-butyl ether 6 parts of water 24 parts of aqueous solution of lithium hydroxide The above components were mixed well and filtered under pressure using a 0.25 μm membrane filter to prepare a red inkjet recording ink DR-2 having a viscosity of 2.1 cps, a surface tension of 43 dyn / cm and a pH of 8.3.

Example 7 Using SU-7 obtained from the above-mentioned amine having a sulfone group and diisocyanate, the following method was used.
The dispersion DOr-1 of Example 7 and the ink Dor-1 for inkjet recording were produced. (Dispersion DOr-1) 20 parts of SU-7 (monoethanolamine neutralized 40% aqueous solution, pH 7.5) 20 parts I. Disperse Orange 73 Powder 25 parts ・ Ethylene glycol 10 parts ・ Defoaming agent Surfynol 104E (manufactured by Nissin Chemical Co.) Some amount (<1 part) ・ Water 145 parts Using the above materials, almost the same as in Example 1 To perform a dispersion treatment to prepare a dispersion having a viscosity of 5.0 cps. The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 12%, an average particle diameter of 148 nm, and a surface tension of 4%.
A dispersion DOr-1 of 2 dyn / cm, pH 7.0 was prepared.

(Ink for Inkjet Recording DOr-1) Dispersion DOr-1 35 parts Diethylene glycol 15 parts Triethylene glycol 5 parts Urea 10 parts Water 35 parts Lithium hydroxide aqueous solution Slight amount The resulting mixture was filtered under pressure using a 0.25 μm membrane filter to prepare an orange inkjet recording ink DOr-1 having a viscosity of 2.6 cps, a surface tension of 41 dyn / cm, and a pH of 9.5.

Example 8 Using SU-8 obtained from the above-mentioned amine having a sulfone group and diisocyanate, the following method was used.
A dispersion DY-2 of Example 8 and an ink DY-2 for inkjet recording were produced. (Dispersion DY-2) 12 parts of SU-8 (50% aqueous solution of neutralized diethanolamine, pH 8.0) I. Disperse Yellow 64 Wet cake prototype (solid content: 30%) 80 parts ・ Ethylene glycol 10 parts ・ Water 100 parts Using the above materials, dispersion treatment was conducted in substantially the same manner as in Example 1, and dispersion was carried out at a viscosity of 3.8 cps. A liquid was prepared. The obtained dispersion was centrifuged in the same manner as in Example 1 to obtain a solid content of 14%, an average particle size of 145 nm, and a surface tension of 4%.
A dispersion DY-2 having 2 dyn / cm and a pH of 6.5 was prepared.

(Ink for inkjet recording DY-2) Dispersion DY-2 35 parts Ethylene glycol 10 parts 1,2,6-hexanetriol 10 parts Urea 5 parts Water 40 parts Lithium hydroxide aqueous solution Amount ・ Sodium lauryl sulfate 0.5 part The above components were mixed well, and filtered under pressure using a 0.25 μm membrane filter. Yellow ink jet recording having a viscosity of 2.4 cps, a surface tension of 38 dyn / cm and a pH of 9.0 was performed. Ink DY-2 was prepared.

Comparative Example 1 In the dispersion formulation of Example 1, SU-1 was used as a dispersant.
(50% aqueous solution of monoethanolamine neutralized, pH 8.
Dispersion treatment was carried out in the same manner as in Example 1 except that 15 parts of a monoethanolamine salt of a naphthalenesulfonic acid type dispersant, Demol N (manufactured by Kao Corporation), was used in place of 0), This was designated as Dispersion C-1 of Comparative Example 1. The dispersion obtained after centrifugation has a solid content of 22%, pH
9.0, surface tension 56 dyn / cm, viscosity 6.8 cp
s, average particle size was 255 nm.

Next, using the dispersion C-1 obtained above, an ink-jet recording ink C-1 of Comparative Example 1 was prepared as follows. (Inkjet recording ink C-1) 43 parts of dispersion C-1 15 parts of diethylene glycol 4 parts of isopropyl alcohol 1 part of monoethanolamine 33 parts of water A well-mixed component is a 0.25 μm membrane filter. The mixture was filtered under pressure to prepare a blue inkjet recording ink C-1 having a viscosity of 2.4 cps, a surface tension of 50 dyn / cm, and a pH of 9.0.

Comparative Example 2 In the dispersion formulation of Example 2, SU-2 was used as a dispersant.
Example 2 was repeated except that a solid content of 20 parts of a ligninsulfonic acid type water-soluble resin (Copartin soda Kop-44, manufactured by Kojin Co., Ltd.) was used instead of (50% aqueous solution of sodium hydroxide, pH 9.0). Perform distributed processing in the same manner as in 1.
This was designated as Dispersion C-2 of Comparative Example 2. The dispersion obtained after centrifugation had a solid content of 19%, pH 8.3, and a surface tension of 54%.
dyn / cm, viscosity 8.0 cps, average particle diameter 330 nm
Met.

Next, using the dispersion C-2, an ink-jet recording ink C-2 of Comparative Example 2 was prepared as follows. (Inkjet recording ink C-2)-Dispersion C-2 45 parts-Thiodiglycol 10 parts-Glycerin 10 parts-Monoethanolamine 1 part-Water 33 parts Mix the above components well, and make a 1 m membrane filter. Pressure filtration using 2.6 cps, surface tension 5
A blue inkjet recording ink C-2 having 0 dyn / cm and a pH of 9.5 was produced.

Comparative Example 3 In the dispersion formulation of Example 2, SU-2 was used as a dispersant.
(50% aqueous solution of sodium hydroxide, pH 9.0) instead of soda salt of styrene-acrylic acid-butyl acrylate copolymer (prototype manufactured by Seiko Chemical Co., Ltd., acid value 15
0, weight average molecular weight 9,000), and the dispersion treatment was carried out in the same manner as in Example 1 to obtain the dispersion C of Comparative Example 3.
-3. The dispersion obtained after the centrifugation had a solid content of 10%, a pH of 8.0, a surface tension of 50 dyn / cm, a viscosity of 8.5 cps, and an average particle size of 160 nm.

Next, using the dispersion C-3, an ink-jet recording ink C-3 of Comparative Example 3 below was prepared. (Inkjet recording ink C-3) 45 parts of dispersion C-3 10 parts of ethylene glycol 10 parts of glycerin 1 part of monoethanolamine 33 parts of water The above components are mixed well, and a 0.25 μm membrane filter is used. The mixture was filtered under pressure to obtain a blue inkjet recording ink C-3 having a viscosity of 2.7 cps, a surface tension of 46 dyn / cm, and a pH of 8.8.

[0078]

Table 1 Synthesis of water-soluble addition polymers SU-1 to SU-8

[0079]

Table 2: Dispersants, dispersants and dyes used in ink jet recording inks

[Evaluation of Performance] Next, with respect to each of the inks for ink jet recording of the examples and comparative examples obtained above,
Evaluation of printing durability, storage stability, printing performance and dyeability on fabric, and process suitability of fabric dyeing were performed by the following evaluation methods and evaluation criteria. Table 3 shows the evaluation results of each ink with respect to each evaluation item obtained as a result.

Print Durability Test An ink jet recording apparatus equipped with a bubble jet recording head having 360 dpi and 64 nozzles was filled with each ink of the examples and comparative examples via an ink supply tube. The driving frequency of the recording apparatus is 6.2 kHz, and the amount of a single dot droplet is 80 ng. Under this condition, every other 3
A continuous ejection test of 3 × 10 ⁸ pulses using two nozzles was performed. Judgment is made at the initial stage and after discharging 3 × 10 ⁸ pulses.
A test document including a document, a solid pattern, and a ruled line was printed, and deterioration of printability was evaluated. Table 3 shows the results. (Evaluation rank) ：: High density, clear characters, no decrease in droplet discharge speed. ：: Vivid characters, uniform and vivid solid printing, ruled line printing without distortion. Δ: Slightly blurred characters, solid printing with reduced density, and ruled line printing with curling. ×: Characters that are blurred and are difficult to read, uneven and thin solid printing, and non-discharges also occurred and disordered ruled line printing. In addition, ◎ and ○ are levels at which there is no practical problem.

Storage Stability Test Ink jet recording inks 50 of Examples and Comparative Examples
ml was packed in a 100-ml shot heat-resistant bottle, sealed tightly, and subjected to an accelerated storage test at 60 ° C. for one month. The determination was made by measuring the viscosity or average particle size after storage and observing the formation of precipitates to determine the quality of storage. Table 3 shows the results. (Evaluation rank) ：: Little change in viscosity and no change in pH. Or
Increase in average particle size is within 20%. ：: The viscosity rise is within 10% of the initial stage, and the amount of precipitate is small. Or, the increase in average particle size is within 20 to 50%. Δ: Change in viscosity was 10 to 50% of the initial value, and precipitation occurred. Alternatively, precipitation occurs and cannot be redispersed. ×: Gelled or hard precipitate. In addition, ◎ and ○ are levels at which there is no practical problem.

Printing on Fabric and Dyeing Test Color printing was performed on the fabric using a bubble jet printer BJC-600 (manufactured by Canon Inc.). The cloth used was polyester decine, which was padded with a 1% aqueous solution of polyvinylpyrrolidone, dried (80% squeezing rate), then adhered to a Mylar film with a double-sided adhesive tape, and recorded with a printer. After color printing, the fabric was peeled off from the mylar film, and then subjected to HT steaming treatment at 180 ° C. for 5 minutes. After this, reduction washing is carried out in the usual manner
After washing with water and drying, a polyester print was obtained. For the judgment of the obtained printed matter, the color density, the color tone and the sharpness were evaluated. (Evaluation rank) A: All good. ：: The boundary between different colors slightly blurred. Δ: Slightly low color density and bleeding. X: Coloring density is slightly low, there is bleeding, and washing fastness is poor.

Process Suitability Test of Fabric Dyeing The same printing and steaming as in “Printing and Dyeing Test on Fabric” was performed using polyester and cotton, and then reduced and washed with water and dried by a conventional method. A cotton print was obtained. The obtained printed matter was evaluated for -1 hand and -2 cotton contamination. (Evaluation rank) -1: Texture evaluation (touch evaluation) ：: Level that has no practical problem. Δ: Somewhat hard but practical range. X: Hard and unusable. -2: Cotton contamination (gray scale evaluation) ：: Grade 4 or higher. Δ: Grade 3 or higher. X: Less than 3rd grade. Table 3 shows the results for the above evaluation items.

[0085]

[Table 3] Table 3: Performance evaluation results

[0086]

As described above, according to the present invention,
For example, fine particles are dispersed in a good state even when the average particle size is 250 nm or less, and even when a dispersion having a high solid content is used, the dispersion has a low viscosity, and the dispersion state is stable over a long period of time. A water-based fine particle dispersion of a disperse dye exhibiting excellent storage stability capable of maintaining the above is obtained. Furthermore, according to the present invention, when the ink is used for inkjet recording using the above-described excellent dispersion, it shows sufficient suitability for a dyeing process such as reducing washing property and cotton stainability after dyeing, When color recording is performed on the fabric, the resulting dyed product is excellent in ejection stability,
Good in fastness, hand and cotton stain.

──────────────────────────────────────────────────続 き Continuation of the front page (51) Int.Cl. ⁶ Identification code FI C09D 11/00 B41J 3/04 101 (72) Inventor Tomoya Yamamoto 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Mariko Suzuki 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Shinichi Hakamada 3-30-2 Shimomaruko 3-chome, Ota-ku, Tokyo Canon Inc. (72) Invention Person: Shiro Shiro 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc.

Claims (2)

[Claims] An aqueous fine particle dispersion containing at least water, a water-soluble organic solvent, a disperse dye and a dispersant, wherein the dispersant is a sulfonic acid obtained from a diol and / or amine having a sulfone group and a diisocyanate. An aqueous fine particle dispersion of a disperse dye, which is a water-soluble addition polymer having a group and a urethane bond or a urea bond. 2. An ink jet recording ink comprising at least a fine particle dispersion of the disperse dye according to claim 1 and a polyhydric alcohol and / or a monoalkyl ether of a polyhydric alcohol.