KR960001061B1 - Blue dye composition - Google Patents

Abstract

This is a new bright blue dye composition which is used in polyester manufacture. The dye composition comprises the compound (I) 20-80wt.%, the compound (II) 10-60wt.%, the compound (III) 0-20wt.%, the compound (IV) 0-10wt.% and compound(V) 0-5wt.%. In the formulas, R is C1-C4 alkyl gp. The above composition can contain additional lignin sulfonate as a dispersing agent. The dye composition has a good color fastness.

Description

Blue dye composition

The present invention relates to light blue dye compositions for use in the synthesis of polyesters and the like, and more particularly to blue dye compositions comprising the compounds of the following structural formulas (I) and (II).

[Formula 1]

[Formula 2]

In the formula, R represents an alkyl group having 1 to 4 carbon atoms.

Anthraquinone-based blue dyes (e.g. CI Disp. Blue 56), which have been used for a long time, have a weak color intensity, which requires a lot of dyeing cost, high pollution to fibers, and low level of uniformity. Due to a lot of influence on the metal ions in the metal complex salts were formed to be precipitated.

In order to remedy these disadvantages of anthraquinone dyes, JP 3,821,338 proposes a blue dye composition composed of two or more of the compounds of the following structural formulas (A) to (D).

[Formula 3]

Wherein R 'represents an alkyl group, allylalkyl group, alkoxyalkyl group, hydroxyalkyl group, chloroalkyl group or alkenyl group, X represents Cl or Br, Y represents cyano group or nitro group, Y' represents alkyl group, An arylalkyl group or an alkoxyalkyl group is represented, Q represents an alkyl group, an aryl group, or an alkoxy group.

The dye compositions described in the German patent have succeeded in ameliorating many of the disadvantages of the anthraquinone dyes, but still have other drawbacks. That is, for example, sublimation fastness (AATCC, 117 to 1989, 200 ℃ 30 seconds), as a result of the polyester pollution degree 2, which is easy to occur the detachment of the dye during high temperature continuous dyeing, low dyeing rate, This means that the color change and contamination rate during permanent setting and ironing are relatively high. In addition, the blended fibers of polyester and cotton at 130 ℃ high temperature dyed for 45 minutes as the composition, the degree of contamination measured by the AATCC standard 3 to 4 grade, so that the color of the polyester and cotton blend fibers when dyed to fully exhibit the unique color As it is difficult, it is pointed out as a big problem considering the recent increase in demand for blended fibers.

In addition, color fastness 4 to 5 and polyester contamination appeared as 4 grades when washing fastness (AATCC, 61 to 1989, 3A) of the above-mentioned dye composition was measured. Can be.

On the other hand, in the case of disperse dyes, the dyeing ratio of the polyester during dyeing shows a lot of difference depending on the chemical structure of each dye, and this difference is more important when used as a composition. That is, the greater the dyeing ratio of the components, the more remaining dyeing after dyeing is completed and the more dye loss, as well as causing severe dyeing wastewater. On the other hand, the above-mentioned composition causes a loss of dye and a large amount of dye wastewater because the affinity with polyester, which is a hydrophobic fiber, is weakened due to the compound having alkoxy group which is a hydrophilic group among the components constituting it. In addition, the dyeing of blended fibers increases the surface contamination, reducing the need to use strong toxic substances.

Accordingly, the inventors have conducted studies to improve the above-described problems of the prior art, as well as excellent physical properties such as various fastness with bright color, which is the most important characteristic of the dye, as well as various dyeing methods, especially high dyeing salts It has been developed a dye composition with excellent yield.

It is an object of the present invention to provide a blue dye composition characterized by containing the compounds of the following structural formulas (I) and (II).

[Formula 4]

[Formula 5]

In the formula, R represents an alkyl group having 1 to 4 carbon atoms.

It is also an object of the present invention to provide a blue dye composition further comprising at least one compound represented by the following formulas (III), (IV) and (V) in addition to the compounds of formulas (I) and (II). It is.

[Formula 6]

[Formula 7]

[Formula 8]

In the formula, R represents an alkyl group of 1 to 4 carbohydrates.

Each compound (I) to (V) used as an essential essential component of the present invention is a known substance. The compound of formula (I) is a strong greenish blue color with intense color and a bright dye. The compound of formula (II) is a weakly reddish blue color with a very bright dye that brightens its own color upon dye composition. The compound of formula (IV) is converted into Zn (CN) ₂ and 1 in DMF solution. It is possible to obtain a yield of 80% through cyanation reaction using an valent or divalent copper catalyst. The compound of formula (III) is a reddish blue color with a strong color intensity, which makes colors more vivid even when a small amount is used in dye composition. The compound of formula (IV) is strong reddish blue, bright in color and strong in strength, and yields 95% by coupling reaction of diazo of bromocyano nitroaniline with N, N-dialkyl meta toluidine. You can get it. The compound of formula (V) is a light reddish blue dye with a weak red color, which is intensely colored and has a very good sublimation fastness (AATCC, 117-1989, 200 ° C, 30 seconds; polyester pollution degree 3), Improve the sublimation fastness of the composition in the dye composition.

The salt composition according to the present invention can be obtained by mixing the compounds of the formulas (I) to (V) mentioned above in a mixed or mixed crystal form. The composition ratio of these compounds may be used in an appropriate composition ratio depending on the intended color or depth of color, but in order to give a typical light blue color, 20 to 80% by weight of the compound of formula (I), based on the total weight of the composition, of formula (II) 10 to 60% by weight of the compound, 0 to 20% by weight of the compound of formula (III), 0 to 10% by weight of the compound of formula (IV) and 0 to 5% by weight of the compound of formula (V). More preferably 40 to 70% by weight of the compound of formula (I), 30 to 50% by weight of the compound of formula (II), 3 to 15% by weight of the compound of formula (III), the compound of formula (IV) 2 to 5% by weight of the compound of formula (V) is composed of 0 to 3% by weight.

The dye compositions according to the invention may also employ sulfonate-based dispersants, such as lignin sulfonates, which are usually suitable for forming the compositions by mixing the aforementioned components in mixed or mixed-crystal form.

The blue dye composition according to the present invention has the following advantages as compared to the dye composition by a conventionally known method.

First, it has excellent sublimation fastness (AATCC, 117 to 1989, 200 ℃, 30 seconds: 3rd degree of pollution with polyester), so that the dye is not removed during high temperature continuous dyeing, and the color is changed during permanent setting and ironing of polyester. And less pollution.

Second, cotton staining of polyester and cotton blend fiber is low (130 ℃, high temperature dyeing for 45 minutes; cotton contamination degree of AATCC standard grade 4) to maintain the intrinsic color as it is.

Third, the washing fastness is excellent (AATCC, 61 to 1989, 3A; color change 4 grade, polyester pollution degree 4) is less discoloration during washing and does not contaminate other fabrics.

Fourth, the compounds of formulas (I) to (V) each have an alkyl group which is a hydrophobic substituent, thereby increasing the hydrophobicity of the dye composition, thereby enhancing the affinity with the polyester, which is a hydrophobic fiber, to increase the degree of dyeing, while the surface is a hydrophilic fiber. Since it prevents dyeing and contamination of cotton fibers by weakening affinity with them, there is no need for a post-treatment process such as reduction and washing after dyeing the blended fibers.

Therefore, the dye composition according to the present invention can be used very effectively for dyeing not only synthetic fibers, such as polyester, but also blended fibers made of polyester and cotton, which are increasing in recent demand.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated further more concretely based on an Example. However, these examples are only for the understanding of the present invention and do not limit the scope of the present invention.

Example 1

54 g of the compound of formula (I), 40 g of the compound of formula (II) (R = ethyl), 3 g of the compound of formula (III) (R = ethyl), and 3 g of the compound of formula (IV) (R = ethyl) To the mixture, 100 g of lignin sulfonate-based dispersant and 500 g of water were added, and then sufficiently dispersed for 2 hours using a dynomil mixing mill. 1 g of the dye composition and 50 g of a polyester dyed cloth are dyed at 130 ° C. for 45 minutes. The dyed cloth is light blue, polyester contamination is 3rd grade and 3rd grade when measuring sublimation fastness (AATCC, 117 to 1989, 200 ℃, 30 seconds), and it is changed when washing fastness (AATCC, 61 to 1989, 3A) It was grade 4, polyester pollution grade 4, and was very good as a grade 5 polyester contamination level 5 when measuring sweat fastness (AATCC, 15 to 1989, acidic). The color is light blue, very similar to commonly used dyes C, I dispersion blue 56.

Example 2

45 g of compound of formula (I), 40 g of compound of formula (II) (R = ethyl), 10 g of compound of formula (III) (R = ethyl), 2.5 g of compound of formula (IV) (R = ethyl), of formula (V 2.5 g of the compound of) is uniformly mixed, and 100 g of lignin sulfonate-based dispersant and 500 g of water are added to the mixture, followed by sufficient dispersion for 2 hours using a dynomil mixing grinder. 1 g of the dye composition and 50 g of a polyester dyed cloth are dyed at 130 ° C. for 45 minutes. The dyed cloth is light blue and has a color similar to that of Example 1 sublimation, laundering, sweatfastness.

Example 3

55.5 g of the compound of formula (I), 36 g of the compound of formula (II) (R = propyl), 3 g of the compound of formula (III) (R = ethyl), 3.5 g of the compound of formula (IV) (R = propyl), V) 2 g of compound (R = ethyl) are uniformly mixed, 100 g of lignin sulfonate-based dispersant and 500 g of water are added to the mixture, and then sufficiently dispersed for 2 hours using a dynomil mixing mill. 1 g of the dye composition and 50 g of a polyester dyed cloth are dyed at 130 ° C. for 45 minutes. The dyed cloth is light blue and has a color similar to that of Example 1 sublimation, laundering, sweatfastness.

Example 4

50 g of the compound of formula (I) and 50 g of the compound of formula (II) (R = ethyl) are uniformly mixed, and 100 g of lignin sulfonate-based dispersant and 500 g of water are added to the mixture, followed by a dynomil mixing grinder for 2 hours. Disperse sufficiently. 1 g of the dye composition and 50 g of a polyester dyed cloth are dyed at 130 ° C. for 45 minutes. The dyed cloth is light blue and has a color similar to that of Example 1 sublimation, laundering, sweatfastness.

[Comparative Example]

After uniformly mixing 59 g of the compound of formula (A) (R '= ethyl) and 1 g of the compound of formula (B) (R' = methoxyethyl) according to the above-mentioned known method, 100 g of lignilsulfonate-based dispersant and 500 g of water is further added to disperse sufficiently for 2 hours to obtain a commercially available blue dye composition.

[Dyeing degree comparison experiment]

The dye composition (A) according to Example 1 of the present invention and the dye composition (B) according to the comparative example were dyed polyester fiber at 130 ° C. for 45 minutes by varying the use ratio of the dye to the dyeing cloth, and then the dyeing degree was measured. The results are shown in Table 1 below. The amount used was dyed using 0.38%, 0.76%, 1.52%, 2.28%, 3.04%, and 3.8%, respectively, by weight of pure dyes relative to the dyeing cloth.

TABLE 1

As can be seen from the above table, there is almost no difference in dyeing degree when dyeing at low concentration, but the dyeing of the composition according to the present invention is superior in dyeing at high concentration.

[Surface contamination comparison experiment]

The dye composition (A) according to Example 1 of the present invention and the dye composition (B) according to the comparative example were blown off the use ratio of the dye to the dyed cloth, and the polyester and cotton fibers were dyed together at 130 ° C. for 45 minutes. The contamination level on the rear surface was measured, and the grades were ranked from grade 1 to grade 5 in the order of high surface contamination in the order of AATCC Transferance scale and the results are shown in Table 2 below. The amount used was dyed using 0.38%, 0.76%, and 1.14%, respectively, as the weight% of the pure dye to the dyeing cloth (50% polyester, 50% cotton).

TABLE 2

As can be seen in Table 2, the higher the concentration dyeing, the less the surface contamination by the composition according to the present invention can be seen that it can be easily confirmed by the naked eye.

Claims (5)

A blue dye composition characterized by containing a compound of the following structural formulas (I) and (II). In the formula, R represents an alkyl group having 1 to 4 carbon atoms. The blue dye composition according to claim 1, further comprising one or more compounds of the following structural formulas (III), (IV) and (V). In the formula, R represents an alkyl group having 1 to 4 carbon atoms. The compound according to claim 1 or 2, wherein 20 to 80% by weight of the compound of formula (I), 10 to 60% by weight of the compound of formula (II), and 0 to 20% by weight of the compound of formula (III) %, 0 to 10% by weight of the compound of formula (IV), 0 to 5% by weight of the compound of formula (V). According to claim 3, 40 to 70% by weight of the compound of formula (I), 30 to 50% by weight of the compound of formula (II), 3 to 15% by weight of the compound of formula (III), Blue dye composition characterized by containing 2 to 5% by weight of the compound of (IV) and 0 to 3% by weight of the compound of the formula (V). The blue dye composition according to claim 1 or 2, further comprising a ligninsulfonate dispersant.