CN111500088B

CN111500088B - Disperse yellow dye composition, dye product and application

Info

Publication number: CN111500088B
Application number: CN202010331510.2A
Authority: CN
Inventors: 王羽蘅
Original assignee: Individual
Current assignee: Individual
Priority date: 2020-04-24
Filing date: 2020-04-24
Publication date: 2021-08-17
Anticipated expiration: 2040-04-24
Also published as: CN111500088A

Abstract

The invention provides a disperse yellow dye composition and a dye product, and the disperse yellow dye composition and the dye product have the characteristics of good lifting power, good level-dyeing property, excellent sunlight resistance, friction resistance, washing fastness and the like when being applied to dyeing or printing of hydrophobic fiber materials.

Description

Disperse yellow dye composition, dye product and application

Technical Field

The present invention relates to a disperse yellow dye composition and dye preparations and their use for dyeing and printing hydrophobic synthetic materials or for the dope-dyeing of hydrophobic synthetic materials.

Background

Disperse dyes are used primarily for dyeing and printing hydrophobic synthetic materials or for the dope dyeing of hydrophobic synthetic materials. Generally, the disperse dyes are classified into a low temperature type, a medium temperature type and a high temperature type according to the sublimation fastness. The low-temperature three primary colors commonly used in the printing and dyeing industry at present are disperse yellow E-GL 200% (C.I.Y54 compound type), disperse red FB 200% (C.I.R60) and disperse blue 2BLN 100% (C.I.B56). Wherein the light fastness of the disperse yellow E-GL is poor at 200 percent and is more than one grade different from that of the disperse red FB 200 percent and that of the disperse blue 2BLN 100 percent. And a large amount of strong acid is consumed in the production process of the intermediate isatin of which the color matching main component is disperse yellow 54, and the pressure ratio of environmental protection treatment is higher, so that some intermediate manufacturers have to stop production, the supply end is short, the price is increased, and the normal production of downstream printing and dyeing enterprises is not facilitated.

The current printing and dyeing process pursues a short flow, for example, the polyester dyeing pretreatment is popular compared with dyeing one bath, but the alkali resistance requirement on disperse dye is higher, and the pH dependence is generally required to be more than 9. The alkali resistance of disperse yellow 54 is pH 3-9, the color fading is more when the pH is more than 9, and the disperse yellow is obviously not suitable for the process of short flow of a dye house. Therefore, the economic low-temperature disperse yellow with excellent performance and light environmental protection pressure can be popularized as a new low-temperature three-primary color.

Patent CN104356688A discloses a yellow disperse dye composition, which is prepared by coupling o-nitroaniline and m-nitroaniline as diazo components with N-ethyl-N-cyanoethylaniline to obtain a yellow dye compound, and then adding a third orange component to obtain a disperse yellow E-GL similar color light instead of old yellow. However, the compounds containing o-nitro and m-nitroaniline as the diazo component have the disadvantage of poor light fastness. The reason is that the nitro group is special, the introduction of the nitro group at the para-position of the azo group can improve the light fastness, and the intramolecular oxidation occurs at the ortho-position, so that the partial breakage of-N-is caused, and the light fastness is reduced. The introduction of nitro groups in the meta-position is not as good as that of para-nitro groups in the sun. Therefore, although this yellow dye can solve the problem of low-temperature type alkali resistance, the light fastness becomes a bottleneck.

2-aminobenzonitrile is used as a pesticide intermediate, the application of the pesticide intermediate to dyes, particularly diazo components of disperse dyes is rarely reported, and no disperse dye containing the structure is considered, researched and utilized for a long time. The disperse dyes using o-chloroaniline as diazoaniline have not been well used, probably because the dyes of this intermediate tend to have a relatively low melting point and are not well developed for practical use. In fact, selection of suitable coupling components can increase the melting point to give dyes with good properties.

Disclosure of Invention

Aiming at the defects in the prior art, the invention provides a disperse yellow dye composition and a dye product, which have the characteristics of excellent fastness, good lifting power, good alkali resistance and the like when being applied to dyeing or printing of hydrophobic fiber materials.

The technical scheme of the invention is as follows:

a disperse yellow dye composition comprises a component A and a component B, wherein the component A is selected from at least one of dye monomer compounds with structures shown in formulas (I-1) to (I-10), the component B is selected from at least one of dye monomer compounds with structures shown in formulas (II-1) to (II-16), based on the component A and the component B, the mass fraction of the component A is 60-99%, and the mass fraction of the component B is 1-40%;

further, the disperse yellow dye composition comprises a component A and a component B, wherein the mass fraction of the component A is 60-99%, and the mass fraction of the component B is 1-40%.

Still further, the disperse yellow dye composition is based on the component A and the component B, wherein the mass fraction of the component A is 80-99%, and the mass fraction of the component B is 1-20%.

Preferably, the disperse yellow dye composition of the invention, wherein the component A is selected from at least one of the formulas (I-1), (I-2), (I-5), (I-9) and (I-10), and the component B is selected from at least one of the formulas (II-1), (II-3), (II-9), (II-12), (II-13), (II-15) and (II-16).

Also preferably, the disperse yellow dye composition of the invention is characterized in that the component A is selected from at least one of the formulas (I-1), (I-2) and (I-9), and the component B is selected from at least one of the formulas (II-1), (II-9), (II-15) and (II-16).

Also preferably, the disperse yellow dye composition of the invention is characterized in that the component A is selected from at least one of the formulas (I-1) and (I-9), and the component B is selected from at least one of the formulas (II-1), (II-15) and (II-16).

When the disperse yellow dye composition is sold as a commodity or applied to coloring textile materials, an auxiliary agent is usually added for post-treatment.

Therefore, the invention also provides a disperse yellow dye product, which contains the disperse yellow dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse yellow dye composition is 0.2-6: 1. the auxiliary agent is selected from one of the following or a mixture of more than two of the following: naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, and sodium lignosulfonate.

The preparation method of the disperse yellow dye product comprises the following steps: mixing the dye monomer compounds (crude dyes) which form the disperse yellow dye composition according to a ratio, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound may be subjected to a pulverization treatment using a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent or water, and then mixed in a certain proportion.

The disperse yellow dye product of the invention is liquid after being ground by a sand mill or a grinding mill, and can be powder and granular after being spray-dried, which is a preparation method known by the technical personnel in the field, and because 100 percent of water cannot be removed in the spray-drying process, a certain amount of water is still allowed to exist in the powder or granular dye product. Due to the particularity of the dye industry, the dye product is difficult to prepare into a pure product, usually has impurities in the preparation process, and the dye product of the invention also allows the existence of trace impurities.

The disperse yellow dye composition provided by the invention is further allowed to be compounded with other dyes to be synergistic to prepare a new composition, or other red, yellow or orange toning components and the like are added.

In the present invention, the dye intermediates represented by the formulae (I-1) to (I-10) and (II-1) to (II-16) may be commercially available or synthesized, and the dye compounds may be conveniently synthesized in a manner known to those skilled in the art, or commercially available products may be used.

The disperse yellow dye composition and the dye product can be applied to dyeing and printing of hydrophobic synthetic materials or the dope dyeing of the hydrophobic synthetic materials.

The dye prepared by the dye composition can dye hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional mode in the industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip-dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, reducing, washing and drying; the direct printing is to carry out dyeing pretreatment, drying and setting on the fabric, print disperse dye color paste on a printing machine, then carry out steaming, fix the color of the dye on the fabric by using a steaming mode, finally wash and tenter setting.

The disperse yellow dye composition and the dye product provided by the invention have the characteristics of good lifting power, good level-dyeing property, excellent sunlight resistance, friction resistance, washing fastness and the like when being applied to dyeing or printing of hydrophobic fiber materials.

Detailed Description

The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:

example 1

In a 150 ml beaker, 24 g of 80% by weight sulfuric acid and 12 g of 2-aminobenzonitrile of the formula (III) were weighed in and 30 g of 42% nitrosylsulfuric acid were added dropwise with stirring. During which the temperature is controlled not to be higher than 20 ℃. After the addition, the reaction is carried out for 2 hours at the temperature of 0-20 ℃ to prepare the diazonium salt.

540 ml of water were added to a 2000 ml beaker, 21.6 g of 98% strength by weight sulfuric acid were added and the temperature was lowered to 0 ℃ by adding an appropriate amount of ice. Then 18 g of the coupling component of the formula (IV) are added with stirring and stirred.

Slowly dripping the prepared diazonium salt, controlling the temperature at 0-5 ℃ and finishing the addition within about 1.5 hours.

After stirring for 1 hour, filtration was carried out and the mother liquor was dark brown. The filter cake was washed with 1000mL of water and was bright orange red.

The filter cake was dried at 90-100 ℃ to give about 30 g of a dry product of the filter cake represented by the formula (I-1) in a weight yield of about 99%.

The filter cake described in example 1 is a compound represented by the formula (I-1):

the maximum absorption wavelength λ max of the monoazo compound in DMF was 440 nm.

Example 2

90 g of the compound of the formula (I-1), 10 g of the compound of the formula (II-1) and 270 g of the dispersing agent MF are mixed with 500 g of water, ground, dispersed and spray-dried to obtain a finished dye product, and the finished dye product can provide yellow color tone of fabrics.

According to a method similar to GB/T2394-2006, 0.4 g of finished dye product is weighed into 500ml of water respectively to prepare a disperse dye suspension. Sucking 50ml of dispersion suspension, mixing with 50ml of water, adjusting the pH value of a dye bath to 4.0 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 4 g of polyester fiber proofing cloth to perform high-temperature high-pressure dyeing, heating to 130 ℃ within 35min, preserving heat for 60min, cooling to 80 ℃ and sampling. The color light of the cloth sample is observed to be the uniform color tone of the old yellow. And observing the level dyeing condition of the cloth sample by naked eyes and electronic color measurement respectively.

Then carrying out reduction washing under the following conditions: NaOH 1g/l, sodium hydrosulfite 2g/l, 85 ℃ 15 min.

GB/T8427-2008, GB/T3921-2008, GB/T3922-2013, GB/T5718-1997, GB/T3920-2008 and GB/T6152-1997 are adopted to test the light fastness, the washing fastness, the perspiration stain fastness, the dry heat fastness, the friction fastness and the hot press fastness of the materials, and the test results are shown in Table 1.

According to a method similar to GB/T2394-2006, O.W.F 1%, 2%, 3%, 4% and 5% dyeing depth sampling is carried out, an electronic color measuring instrument is used for testing the K/S value of the cloth sample to observe the dyeing depth condition of the cloth sample, and the measurement result is shown in Table 1.

Table 1 units: stage

Examples 3 to 23

According to the method of the example 2, the component A, the component B and the dispersant with different weights shown in the table 2 are mixed and blended with 500 g of water to prepare slurry, and the slurry is ground, dispersed and spray-dried to obtain the finished product, wherein the finished product can provide yellow to yellowish-brown color tone of the fabric.

85A and 83A in table 2 are lignin 85A and lignin 83A, respectively.

TABLE 2

Comparative example 1

The yellow disperse dye prepared in example 2 of patent CN104356688A is added with 10 g of MF dispersant to reduce the strength, and the prepared product is used as a comparative example 1:

example 24

The disperse dyes prepared in the above examples 3-23 and the finished dye of the comparative example 1 were dyed according to the method of example 2, and the level dyeing of the fabric was observed with naked eyes and electronic color measurement, respectively.

GB/T8427-2008, GB/T3921-2008, GB/T3922-2013, GB/T5718-1997, GB/T3920-2008 and GB/T6152-1997 are adopted to test the light fastness, the washing fastness, the perspiration stain fastness, the dry heat fastness, the friction fastness and the hot press fastness of the materials, and the test results are shown in Table 3.

According to a method similar to GB/T2394-2006, O.W.F 1%, 2%, 3%, 4% and 5% dyeing depth sampling is carried out, K/S values of the cloth samples are tested by an electronic color measuring instrument to compare the dyeing depth conditions of the cloth samples, and the measurement results are shown in Table 3.

Table 3 units: stage

As can be seen from Table 3, the light fastness of the invention is greatly improved compared with that of comparative example 1, the level-dyeing property and the deep dyeing property are good, the color is fuller, and other various fastnesses are excellent.

Comparative example 2

Comparative example 2 was prepared with disperse yellow E-GL 200% manufactured by Longsheng corporation.

Example 25

The finished dye of example 2, comparative example 2 disperse yellow E-GL 200%, was subjected to a basic dyeing test:

according to a method similar to GB/T2394-2006, 0.8 g of the finished dye product in example 2 is weighed into 500ml of water to prepare a disperse dye suspension. Respectively sucking 50ml of the dispersion suspension and 50ml of water to mix, preparing 4 cups in the same step, regulating the pH of a dye bath to 4.5 by using acetic acid for the first cup, regulating the pH of the dye bath to 10, 11 and 12 by using sodium hydroxide for the other three cups, heating to 60 ℃, simultaneously adding 4 g of polyester fiber sample cloth to carry out high-temperature high-pressure dyeing, heating to 130 ℃ within 35min, keeping the temperature for 60min, cooling to 80 ℃, sampling, and testing the pH value of residual liquid. And (3) drying the sample cloth, carrying out electronic color measurement by taking a cloth sample with pH 4.5 as a standard, and observing the color light of the cloth sample to be a uniform color tone of the old yellow.

0.8 g of the finished product of comparative example 2 was weighed, the above steps were repeated, and the alkali resistance of the two products was compared, and the results are shown in Table 4.

TABLE 4

As can be seen from Table 4, the low-temperature disperse dye composition with good light fastness has improved alkali resistance compared with 200% of commercially available disperse yellow E-GL, can be applied to a short-flow process of a dye house, and has wider applicability.

Claims

1. The disperse yellow dye composition is characterized by comprising a component A and a component B, wherein the component A is selected from at least one of dye monomer compounds with structures shown in formulas (I-1) to (I-10), the component B is selected from at least one of dye monomer compounds with structures shown in formulas (II-1) to (II-16), based on the component A and the component B, the mass fraction of the component A is 60-99%, and the mass fraction of the component B is 1-40%;

2. the disperse yellow dye composition according to claim 1, wherein the mass fraction of the component A is 80-99% and the mass fraction of the component B is 1-20% based on the component A and the component B.

3. The disperse yellow dye composition according to claim 1, wherein the component A is at least one selected from the group consisting of formula (I-1), (I-2), (I-5), (I-9) and (I-10), and the component B is at least one selected from the group consisting of formula (II-1), (II-3), (II-9), (II-13) and (II-16).

4. The disperse yellow dye composition according to claim 1, wherein the component A is at least one selected from the group consisting of formula (I-1), (I-2) and (I-9), and the component B is at least one selected from the group consisting of formula (II-1), (II-9) and (II-16).

5. The disperse yellow dye composition according to claim 1, wherein the component A is at least one selected from the group consisting of formula (I-1) and formula (I-9), and the component B is at least one selected from the group consisting of formula (II-1) and formula (II-16).

6. The disperse yellow dye composition according to any one of claims 1 to 5, wherein the disperse yellow dye composition consists of a component A and a component B.

7. A disperse yellow dye preparation comprising the disperse yellow dye composition of claim 1 and an auxiliary.

8. The disperse yellow dye preparation according to claim 7, wherein the weight ratio of the auxiliary agent to the disperse yellow dye composition is 0.2-6: 1.

9. a disperse yellow dye preparation according to claim 7 or 8, wherein the auxiliaries are selected from one or a mixture of two or more of the following: naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate and benzyl naphthalene sulfonic acid formaldehyde condensate.

10. Use of a disperse yellow dye composition according to claim 1 for dyeing and printing hydrophobic synthetic materials or for the dope-dyeing of hydrophobic synthetic materials.