JPH11302555A - Disperse dye mixture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject mixture maintaining excellent pH stability, eliminating an excessively strong reddish color, exhibiting excellent dyeing levelness and excellent adsorptivity and useful for dyeing polyester fibers, etc. by mixing a specific orange color disperse dye with a specified orange color disperse dye having different substituents. SOLUTION: This disperse dye mixture comprises a mixture of (A) an orange color disperse dye comprising 4-[2,6-dibromo-4-nitriphenyl)azo]-1-[N-ethyl-N-(2- cyanoethyl)amino]benzene with (B) an orange color disperse dye of formula II [X is H or C1; R is cyanoethyl (R'), benzoyloxyethyl (R") or benzyl (R''')]. The component B is used in an amount of 0.2-5 weight times that of the component A. The mixture preferably uses a mixture of the compound of formula II (R is R" or R''') with the compound of formula II (R is R') in a weight ratio of 2:1 to 1:2 as the component B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a disperse dye mixture, and more specifically, it has excellent pH stability and levelness, and has a characteristic of adsorbing to a fiber in a dyeing process (particularly, a temperature at which adsorption is started).
Relates to a mixture of orange-based disperse dyes which is remarkably excellent.

[0002]

BACKGROUND OF THE INVENTION Orange disperse dyes C.I. I. Dispers
e Orange 30 is known as an orange-based disperse dye for three primary colors having excellent high-temperature dyeability, but has poor pH stability. Furthermore, regarding the adsorption characteristics to the fibers in the dyeing process, the adsorption start temperature is high, and the influence of the dye concentration on the adsorption start temperature is large. When using at a high concentration, the adsorption start temperature becomes extremely high. When used in combination with a dye having a low temperature, dyeing may not be completed.

On the other hand, the orange disperse dye represented by the structural formula [A] is a C.I. I. Disperse Orange
e61: p when polyester fiber is dyed
It is known as a dye having a low H dependence, that is, a pH stability is good, but the hue is too reddish and the range of use as an orange dye for general three primary colors is narrow, and the leveling property is extremely poor.
C. above. I. Disperse Orange 30
There is also a problem in the adsorption characteristics to fibers in the same dyeing process as described above.

[0004]

SUMMARY OF THE INVENTION Therefore, one of the objects of the present invention is to provide a conventional C.I. I. An object of the present invention is to provide an orange dye component which does not have the drawbacks of Disperse Orange 30 and further exhibits performance exceeding this. Another object of the present invention is to eliminate excessively strong reddishness and improve levelness while maintaining excellent pH stability of the orange disperse dye represented by Structural Formula [A]. The purpose is to improve the adsorption characteristics to fibers during the dyeing process.

[0005]

The present inventors have conducted intensive studies in view of the above-mentioned circumstances, and as a result, when a dye of the structural formula [A] shown above is mixed with an orange dye having a specific structure, the mixture is used alone. As compared with the case of use, reddishness which is too strong disappears, leveling properties and adsorption characteristics to fibers during the dyeing process are remarkably improved. I. It has been found that not only is it a suitable replacement for Disperse Orange 30, but it also provides a dye component that significantly exceeds its performance.

That is, the gist of the present invention is to provide an orange-based disperse dye represented by the structural formula [A] shown above and 0.1% of the dye.
It is present in a disperse dye mixture obtained by mixing 2 to 5 times by weight of at least one orange disperse dye represented by the above general formula [B]. Hereinafter, the present invention will be described in detail. The dyes represented by the formulas [A] and [B] used in the present invention can be easily produced according to known methods.

The dye itself represented by the above formula [A] is
C. I. Known as Disperse Orange 61, for example, 2,6-dibromo-4 by a conventional method.
-Nitroaniline is diazotized and is converted to N-ethyl-N
-Can be prepared by coupling with cyanoethylaniline. In the dye represented by the formula [B], those in which X is a hydrogen atom and R is a benzoyloxyethyl group are particularly C.I. I. Disp
known as Orange Orange 73, and the others are prepared in the same manner as the production method thereof, that is, the following general formula [C]

[0008]

Embedded image (Wherein X has the same meaning as defined for formula [B]) by diazotizing an aniline represented by the following general formula [D],

[0009]

Embedded image (Wherein, R has the same meaning as defined for formula [B]) by coupling with benzenes represented by the general formula. In the present invention, the orange disperse dyes represented by the formulas [A] and [B] are mixed and used, and the mixing ratio is such that the component [B] is 0.2 to the component [A]. ５5 times by weight, preferably 0.3 to 2 times by weight.

Further, a dye wherein R in the formula [B] is a benzoyloxyethyl group or a benzyl group, and a dye represented by the formula [B]
When used in combination with a dye in which the middle R is a cyanoethyl group, the effects of improving leveling properties and adsorption properties to fibers are particularly remarkable. In such a case, the dye (B) in which R in the formula [B] is a benzoyloxyethyl group or a benzyl group
₁ ) and a dye (B ₂ ) wherein R in the above formula is a cyanoethyl group
Is usually 2: 1 to 1: 2, preferably 1.5: 1 to 1: 1.
5 used in a B ₁ : B ₂ weight ratio.

In the present invention, each of the above-mentioned disperse dyes is used in combination as an orange-based component. However, in order to obtain an orange dye having a desired color tone, another orange dye or a yellow dye may be mixed. In addition, in order to dye to a desired color tone, it can be dyed by blending with a red dye and a blue dye. For example, black is about 40% by weight of the orange dye mixture according to the invention, CI Disperse Violet 93.
1 and about 35% by weight of CI Disperse Bl.
ue 291 in a proportion of about 25% by weight. In using the disperse dye mixture of the present invention, for example, naphthalenesulfonic acid-
It is necessary to prepare a disperse dye composition by mixing with a known anionic dispersant such as a formalin condensate or a ligninsulfonic acid-formalin condensate and subjecting the dye cake to a dispersion treatment.

The disperse dye mixture of the present invention is used for dyeing polyester fibers, diacetate fibers, triacetate fibers and nylon fibers, but is mainly used for dyeing polyester fibers. The target fiber may be a single fiber or a mixture with other fibers such as cotton, rayon, and wool. Although various methods can be applied as the dyeing method, the dye mixture of the present invention shows particularly excellent leveling properties and adsorption characteristics when applied to the exhaust dyeing method. The dyeing conditions in the exhaust dyeing are not particularly limited. For example, the dyeing temperature is about 95 to 140 ° C., and the dyeing bath pH is 4 to 10.
It is about 5.

[0013]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist. Reference Example <Preparation of each disperse dye composition> (1) A sand grinder was prepared by dissolving 44 g of the disperse dye represented by the structural formula [A] shown above together with 19 g of a naphthalenesulfonic acid-formalin condensate, 37 g of a ligninsulfonic acid-formalin condensate, and 300 g of water. For 5 hours and spray-dried to obtain a powdery dye composition A. (2) 40 g of the disperse dye of B-1 in Table 1 is wet-ground with a sand grinder for 5 hours together with 20 g of a naphthalenesulfonic acid-formalin condensate, 40 g of a ligninsulfonic acid-formalin condensate, and 300 g of water, and spray-dried. As a result, a powdery dye composition B-1 was obtained. (3) 50 g of the disperse dye of B-2 in Table 1 below is wet-ground with a sand grinder for 5 hours together with 17 g of a naphthalenesulfonic acid-formalin condensate, 33 g of a ligninsulfonic acid-formalin condensate, and 300 g of water, and spray-dried. As a result, a powdery dye composition B-2 was obtained.

[0014]

[Table 1] Examples 1 to 4 and Comparative Examples 1 to 4 The mixed dyes prepared by blending the disperse dye compositions of A and B-1 to B-2 prepared in the reference examples at the ratios shown in Table 2 were used, and the results are shown below. Each of the dyeing tests was performed according to the method and evaluated. Table 2 shows the results. <Dyeing test> (1) High-temperature dyeing (acidic dyeing) A polyester tropical cloth (using processed yarn) is dyed at a density of 1
/ 1N, using 1 g / L of an anionic leveling assistant, adjusting the pH to 5.0 ± 0.5 with acetic acid and sodium acetate,
Dyeing was performed at 135 ° C. for 30 minutes at a bath ratio of 1:10. The obtained dyed cloth was washed with 2 g / L of caustic soda, 2 g / L of hydrosulfite, and 1 g of anionic / nonionic surfactant.
Using L, reduction washing was performed at 80 ° C. for 10 minutes. (2) High temperature dyeing (dyeing in dyeing bath pH 7) The above high temperature dyeing (dyeing bath was adjusted to pH 7.0 ± 0.1 with potassium dihydrogen phosphate and sodium tetraborate before dyeing was started) Acid staining). (3) Patchy dyeing This is a special dyeing method for levelness evaluation using a color pet dyeing machine. A polyester tropical cloth is wrapped around a cylindrical holder having holes (5 mm) for circulating the dye liquor at equal intervals. At a dyeing concentration of 1 / 6N, no leveling assistant was used, and pH 5.0 ± 0.5 with acetic acid and sodium acetate.
And the dyeing pot is adjusted to a bath ratio of 1:30. This is set in a color pet dyeing machine preheated to 60 ° C., rapidly heated to 130 ° C. at about 6 ° C./min, and then rapidly cooled. After dyeing, the obtained dyed cloth is washed with water and dried. (4) Adsorption characteristic to fiber (adsorption start temperature characteristic) Dyeing density of polyester tropical cloth (using processed yarn) of 1
/ 1N, using 1 g / L of an anionic leveling assistant, adjusting the pH to 5.0 ± 0.5 with acetic acid and sodium acetate,
Dyeing was performed at 135 ° C. for 30 minutes at a bath ratio of 1:10. At that time, the temperature was raised from room temperature to 135 ° C. at a rate of 1 ° C./min, during which, for example, 90 ° C., 100 ° C., 110 ° C., 120 ° C.,
The dyed cloth is taken out at 35 ° C., and the obtained dyed cloth is washed with water. <Evaluation method> (1) pH stability The surface concentration of the dyed cloth obtained by dyeing at a dyeing bath pH of 5 and pH 7 at a dyeing concentration of 1 / 1N at a high temperature was measured according to the Kubelka-Munk formula, and according to the following formula. Calculate the pH dependence. The change in hue is visually determined.

Concentration ratio = (surface density of dyed cloth at high temperature dyeing at dyeing bath pH 7) / (surface density of dyed cloth at high temperature dyeing at dyeing bath pH 5) × 100 (2) Leveling property Obtained by patchy dyeing The casing spot formed on the innermost layer of the dyed cloth was visually judged according to the following criteria.

Grade 5 (extremely excellent)-no casing spot is seen. Grade 4 (good)-Slight casing spot is seen. Grade 3 (standard)-A little casing spot is seen. Grade 2 (poor)-fairly clear Casing spots can be seen Class 1 (markedly inferior)-Casing spots can be markedly marked (3) Adsorption characteristics to fibers High-temperature dyeing at dyeing concentrations of 1 / 2N and 1 / 1N, each dyeing obtained in the dyeing process. The surface concentration of the cloth is measured according to the Kubelka-Munk equation, and the adsorption rate is calculated according to the following equation.

Adsorption rate = (surface density of dyed cloth at each temperature during dyeing process / surface density of dyed cloth at 135 ° C. for 30 minutes dyeing) × 100 (%) The temperature at an adsorption rate of 20% is the adsorption start temperature. And

[0018]

[Table 2]

[0019]

The disperse dye mixture of the present invention is very useful because it has excellent pH stability, leveling properties, and adsorption properties to fibers during the dyeing process.

Claims (2)

[Claims] 1. An orange disperse dye represented by the following structural formula [A] mixed with at least one kind of orange disperse dye represented by the following general formula [B] in an amount of 0.2 to 5 times the weight of the dye. A disperse dye mixture comprising: Embedded image Embedded image (Wherein each X independently represents a hydrogen atom or a chlorine atom, and R represents a cyanoethyl group, a benzoyloxyethyl group or a benzyl group.) 2. An orange disperse dye represented by the above general formula [B], a dye (B ₁ ) wherein R in the above general formula [B] is a benzoyloxyethyl group or a benzyl group;
2. The disperse dye mixture according to claim 1, wherein a mixture is used in which the weight ratio (B ₁ : B ₂ ) to the dye (B ₂ ) in which R is a cyanoethyl group (B ₁ : B ₂ ) = 2: 1 to 1: 2.