JPH10298445A - Crystalline monoazo disperse dye and its application - Google Patents

Abstract

(57) [Problem] To provide a blue monoazo disperse dye capable of performing good dyeing even under severe conditions at a high temperature. SOLUTION: Among peaks having a diffraction angle (2θ) in the range of 5 ° to 30 ° by X-ray diffraction using Cu-Kα ray, 2θ is 6.3 °, 8.8 °, 13.0 ° and 23.6. The following formula (I) characterized in that a peak having a large intensity is shown in °.
A crystalline monoazo disperse dye represented by the formula: Embedded image

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a monoazo disperse dye, and more particularly, to a blue monoazo disperse dye having a novel crystal form and having excellent dispersibility under severe conditions at high temperatures, and a hydrophobic dye using the same. The present invention relates to a method for coloring a conductive fiber material.

[0002]

2. Description of the Related Art In recent years, various rationalization methods for coloring a hydrophobic fiber material have been performed. For example, when a polyester fiber is dyed using a disperse dye, a liquid jet dyeing method for cloth and a dyeing method for yarn are used. A cheese dyeing method or a package dyeing method is frequently used.

[0003] In these dyeing methods, a dense fiber layer in which a number of layers of fibers are wound is kept stationary, and a dye dispersion is forcibly circulated in the fiber layer for dyeing. As described above, it is required that the dye particles dispersed in the dye bath are fine particles and that the dispersion stability in the dye bath is excellent. If the dye particles become large, the fiber layer causes the dye particles to be filtered, which results in poor dye penetration into the interior of the fiber, or dyeing of the inner or outer layer due to the adhesion of aggregates, or the attachment of the dye only to the fiber surface. Problems such as a decrease in fastness such as rub fastness occur.

Therefore, the dye used in such a dyeing method has good dispersibility in a dyeing bath and does not decrease in a wide temperature range from room temperature to a high temperature at which actual dyeing occurs. is required. However, the dispersibility of the dye in a high-temperature dyeing bath generally tends to decrease, and as a result, the aggregated dye adheres to the surface of the material to be dyed as described above, and overlaps with multiple layers. The dyeing density differs between the outer layer portion and the inner layer portion, and a dyed product having a uniform density cannot be obtained.

Particularly recently, from the viewpoint of resource saving and energy saving, (1) lowering the bath ratio of the dyeing bath (reducing the ratio of the weight of the dyeing material to the weight of the dyeing solution from 1:30 to 1:10), (2) ) Decrease in the proportion of dispersant used (the ratio of the weight of disperse dye to the weight of dispersant in micronization is reduced from 1: 3 to 1: 1), and (3)
Shorter and higher temperature of dyeing conditions (1 hour to 13 at 130 ° C)
(0.5 hours at 5 ° C), and dyeing conditions are shifting to more severe conditions. All of these conditions have a disadvantageous effect on the dispersion stability of dyes. Even dyes having good properties have poor dispersion stability under severer recent dyeing conditions.

The following formula (I)

Embedded image

[0007] The disperse dye represented by
No. 27 or JP-A-58-104952, 1-amino-2,4-dinitro-6-bromobenzene (hereinafter referred to as diazo component) is diazotized, and then the obtained diazotized product is obtained. With 1-N, N-di (methoxyethyl) amino-2-methoxy-5-acetylaminobenzene (hereinafter, referred to as a coupling component) or a coupling reaction solution obtained by the above method. After the neutralization, an organic solvent can be added to the neutralized solution, and then heat treatment can be performed. This known monoazo dye can uniformly dye polyester fibers under conventional mild dyeing conditions, and has excellent fastnesses. However, when dyeing is carried out under the above-mentioned severe conditions, the dispersibility of the above-mentioned known dye is remarkably reduced, and it becomes difficult to obtain a dyed product having a uniform dyeing concentration.

The known dyes are also insufficient in compatibility with various dyeing auxiliaries. For example, the known dyes have poor high-temperature dispersion stability in the presence of silica glass, and therefore, may be used in combination with reactive dyes. Dyeing polyester / cotton blends in the presence of oxalate results in uneven dyeings. Furthermore, there is a problem that the compatibility with other dyes is poor, and when known dyes are used in combination with other dyes, color blur and uneven dyeing occur.

[0009]

The present inventors have made intensive studies to solve the above-mentioned problems and to provide a dye capable of performing good dyeing under severe conditions at high temperatures.
There is a dye having a novel crystal form different from the known dye obtained as an amorphous crystal by the above-mentioned conventional production method,
The novel dye was found to have good dispersion stability at high temperatures and under severe dyeing conditions. The present inventor has further studied and found that the stability of the dispersion state of the dye composition in the high-temperature dyeing bath is not only the size of the dye particles,
The present invention was also found to have a significant effect on crystallinity, and it was only by dyeing with the above-described novel dye that a dyed product having excellent uniformity and fastness was obtained, and the present invention was completed.

[0010]

That is, the present invention provides a Cu—
The diffraction angle 2θ is 5 ° or more 3 by X-ray diffraction using Kα ray.
Of the peaks appearing in the range of 0 ° or less, the 2θ is 6.
Crystalline monoazo disperse dyes represented by the above formula (I) characterized by showing peaks with high intensity at 3 °, 8.8 °, 13.0 ° and 23.6 °, and the disperse dyes are used. The present invention provides a method for coloring a hydrophobic fiber material.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The novel disperse dye represented by the above formula (I) of the present invention can be produced, for example, as follows. First, the diazo component is diazotized by a conventional method, and the resulting reaction solution containing the diazotized product is diluted with a dilute sulfuric acid medium at a temperature of -8 to 10 ° C, preferably -5 to 5 ° C, for 0.5 to 15 ° C. The coupling reaction is carried out with the above-mentioned coupling component for a time. The dye cake obtained by filtering off the crystals precipitated after the coupling reaction is an amorphous crystal.

Therefore, for example, the reaction solution after the completion of the coupling reaction is used as it is, or after neutralization to pH 6 to 7, the reaction solution is reduced to 60 to 13
Stirring is performed at a temperature of 0 ° C., preferably 70 to 90 ° C. for 0.5 to 30 hours, preferably 1 to 10 hours. By the treatment, the disperse dye of the present invention can be obtained. Further, for example, the dye cake of the amorphous crystals filtered out above
7.5 to 12.0, particularly preferably dispersed in an aqueous medium having a pH of 8 to 10, and optionally a formaldehyde condensate of naphthalenesulfonic acid, a concentrate of waste sulphite pulp mainly composed of sodium ligninsulfonate, etc. At a temperature of 60 to 130 ° C, preferably 70 to 90 ° C, in the presence of a dispersant of 0.5 to 30 ° C.
The disperse dye of the present invention can also be obtained by stirring for 1 hour, preferably 1 hour to 10 hours. pH 7.5-12.0
Examples of the alkali agent for adjusting the pH include sodium hydroxide, potassium hydroxide, sodium carbonate, calcium carbonate, sodium hydrogen carbonate, and sodium phosphate.

Next, the crystalline monoazo disperse dye of the present invention and the known disperse dye (amorphous crystal) represented by the above formula (I) will be described with reference to the drawings. 1 and 2 are X-ray diffraction diagrams recording the state of diffraction by the Cu-Kα ray in the powder X-ray diffraction method. The horizontal axis indicates the diffraction angle (2θ), and the vertical axis indicates the diffraction intensity. FIG. 1 is an X-ray diffraction diagram of the crystalline monoazo disperse dye of the present invention. In particular, the diffraction angles (2θ) are 6.3 °, 8.8 °, 13.0 ° and 23.6.
The characteristic feature is that a strong peak is observed at °. Further, in addition to the above-mentioned peak having a large intensity, 7.7 is further added.
-, 9.4-, 20.3 °, 22.0 °, 24.6 °, 24.9 ° and 2
A peak having a small intensity is observed at 5.7-. On the other hand, FIG.
Is an X-ray diffraction pattern of a known disperse dye, and it can be seen that the crystal form is clearly different from the crystalline disperse dye of the present invention in FIG. The diffraction angle by the X-ray diffraction method is
It is known that if they are of the same crystal type, they match with an error of about ± 0.1.

Based on this difference in crystal form, the behavior of the dye particles during dyeing is completely different between the known disperse dye and the crystalline monoazo disperse dye of the present invention. Even if the hydrophobic fiber material is colored at a temperature and under severe conditions, a good dyed product can be obtained.

As the hydrophobic fiber material to which the monoazo disperse dye of the present invention can be applied, polyethylene terephthalate,
Polyester fiber such as polycondensate of terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane, acetate fiber such as triacetate and diacetate, or natural fiber such as cotton and wool and the above polyester fiber or acetate fiber Blended products and blended products are included. The coloring of the polyester fiber using the monoazo disperse dye of the present invention is performed by dispersing a dispersant such as a condensate of naphthalenesulfonic acid and formaldehyde, a higher alcohol sulfate, or a higher alkylbenzene sulfonate, and the above dye in an aqueous medium. It is carried out by a conventional method of dyeing or printing using a dyeing bath or printing paste prepared by the above. In addition, for example, in the case of dip dyeing, a high temperature dyeing method as described above, a carrier dyeing method, a dyeing treatment method such as a thermosol dyeing method can be applied, and even if severe dyeing conditions are employed in these methods. Since the monoazo disperse dye of the present invention is excellent in dispersion stability, it can be used to dye polyester fiber, acetate fiber or a blend of these and other fibers. Specifically, under severe conditions of dyeing a polyester fiber or the like at a dyeing temperature of 125 to 140 ° C., a dyeing bath ratio of 15 times or less, and a dispersant use ratio of less than 3 times by weight of the dispersant in an aqueous medium, Exhaust dyeing in the presence is also possible. In addition, when the monoazo disperse dye of the present invention is used, ultrafine fibers such as microfibers, particularly polyester fibers having a denier of 1 denier or less, polyester fibers composed of irregular cross-section yarns, different shrinkage blended yarns or multiphase hybrid yarns, ,
New materials such as polyester fibers spun at high speed, especially spun at a speed of 6000 m / min or more, can be dyed relatively easily in dark color and uniformly. A dyed product showing fastness can be obtained.

In some cases, if an acidic substance such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate is added to the dyeing bath,
Even better results are obtained. In addition, the monoazo crystalline disperse dye of the present invention may be used in combination with other dyes, and good results such as improvement in dyeability may be obtained by blending the dyes.

[0017]

The crystalline monoazo disperse dye of the present invention can be used at a high temperature, for example, at a bath ratio of the weight of the material to be dyed to the weight of the dyeing liquid of 1:10, and the ratio of the weight of the disperse dye cake to the weight of the dispersant. The dispersion stability is very good even under severe dyeing conditions of 1: 1 and dyeing conditions of 135 ° C for 0.5 hours, and the obtained dyed fabric is dyed uniformly and has various properties such as fastness to rubbing. It has excellent robustness. Therefore, the dye of the present invention is very useful from the viewpoint of resource saving and energy saving.

[0018]

EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. The parts and percentages in the examples are, respectively,
Parts by weight and% by weight are indicated.

Reference Example 1 26 parts of the above diazo component was diazotized using 43% nitrosyl sulfuric acid to obtain a diazotized solution. Separately, 29 parts of the above coupling component was dissolved in a 5% aqueous sulfuric acid solution, and the diazotized solution was added dropwise to this solution at 0 to 5 ° C. After the completion of the reaction, the precipitated crystals were separated by filtration, washed with water, and a part of the cake was dried to obtain a monoazo dye represented by the above formula (I). When the powder of this monoazo dye was analyzed by an X-ray diffraction method, it was found to be an amorphous crystal as shown in the X-ray diffraction diagram shown in FIG.

Example 1 On the other hand, about 50 parts of the remaining crystals separated by filtration and washed with water in Reference Example 1 were suspended in 500 ml of a 1% by weight aqueous solution of sodium carbonate, and the temperature was raised to 70 to 80 ° C. Heat treatment was performed for an hour. Thereafter, the mixture was cooled to room temperature, filtered and dried. When the obtained crystal was analyzed by an X-ray diffraction method, it was in a crystal form as shown in the X-ray diffraction diagram of FIG.

Example 2 One part of the novel crystalline monoazo dye obtained in Example 1 was atomized and dispersed in an aqueous medium together with one part of a naphthalenesulfonic acid-formaldehyde condensate and one part of a higher alcohol sulfate. 10 parts of tetron jersey (polyester cloth, manufactured by Teijin Limited) is immersed in 100 parts of a dye bath containing 0.1 part of a powder obtained by drying the dye dispersion,
Stained for 0 minutes. After the obtained dyed product was soaped, washed with water and dried, a blue dyed cloth having a uniform and uniform dyeing was obtained. From this, it was found that the dispersibility of the dye of the present invention under the dyeing conditions was good. The rub fastness of the obtained dyed fabric was 5th grade, which was good.

Comparative Example 1 A dyeing test was carried out in the same manner as in Example 2 using the amorphous monoazo dye having the X-ray diffraction pattern shown in FIG. Partial assembling occurred and an uneven dyed cloth was obtained. The rub fastness of the dyed cloth is 1
It was inferior to the class.

Comparative Example 2 The same dyeing test as in Example 2 was carried out using the monoazo dye prepared by the method described in Example 2 of JP-A-58-104952. The dispersibility was slightly improved as compared with Comparative Example 1, but
After all, an uneven dyed fabric was obtained, and the fastness to rubbing was 3-4 class.

Example 3 A novel monocrystalline dye having a crystalline property obtained in Example 1 was used, and a cross-woven cloth of polyester fibers having a fiber diameter of 2 denier and 0.01 denier was used instead of the tetron jersey cloth. A dyeing test was performed in the same manner as in Example 2 except for the above. The obtained dyed product had the same color and the same density between different deniers, and also had excellent levelness and various fastnesses.

Example 4 Dyeing was carried out in the same manner as in Example 2 except that the novel crystalline monoazo dye obtained in Example 1 was used, and a high-speed spun polyester woven fabric was used instead of the tetron jersey fabric. Tested. The leveling properties and various fastnesses of the dyed products obtained were likewise excellent.

[Brief description of the drawings]

FIG. 1 is an X-ray diffraction diagram of the crystalline monoazo disperse dye of the present invention.

FIG. 2 is an X-ray diffraction diagram of a conventional monoazo disperse dye.

Claims (5)

[Claims] 1. X-ray diffraction by Cu-Kα ray, among peaks having a diffraction angle 2θ in the range of 5 ° to 30 °, the 2θ is 6.3 °, 8.8 °, 13.0 °. And 2
A crystalline monoazo disperse dye represented by the following formula (I), which shows a peak having a large intensity at 3.6 °. Embedded image 2. The diffraction angle 2θ is 7.7 °, 9.4.
2. The crystalline monoazo disperse dye according to claim 1, wherein the monoazo disperse dye has a low intensity peak at 20.3 °, 24.6 °, 24.6 °, 24.9 ° and 25.7 °. 3. A method for coloring a hydrophobic fiber material, comprising using the crystalline monoazo disperse dye according to claim 1 or 2. 4. The method of claim 3, wherein the hydrophobic fiber material comprises polyester fibers of 1 denier or less. 5. The method according to claim 3, wherein the hydrophobic fiber material comprises polyester fibers spun at a speed of 6000 m / min or more.