CN112574595A

CN112574595A - Blue-to-black disperse dye composition and dye product

Info

Publication number: CN112574595A
Application number: CN202011614446.5A
Authority: CN
Inventors: 何旭斌; 陶建国; 杨日升; 王海丰; 刘秋红
Original assignee: ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD; Zhejiang Longsheng Dye Chemical Co ltd; Zhejiang Longsheng Group Co Ltd
Current assignee: ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD; Zhejiang Longsheng Dye Chemical Co ltd; Zhejiang Longsheng Group Co Ltd
Priority date: 2020-12-31
Filing date: 2020-12-31
Publication date: 2021-03-30
Anticipated expiration: 2040-12-31
Also published as: CN112574595B

Abstract

The invention discloses a blue-to-black disperse dye composition, which comprises a component A, a component B, a component C and a component D, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), and the component D is selected from at least one of the following formulas (IV) to (V).

Description

Blue-to-black disperse dye composition and dye product

(I) technical field

The invention relates to a blue-to-black dye composition and a dye product, in particular to an environment-friendly blue-to-black disperse dye composition and a dye product suitable for printing and dyeing hydrophobic fiber materials.

(II) background of the invention

The blue-black series dye in the disperse dyes has the largest usage amount, and the traditional dye composition which is made by mixing C.I. disperse blue 291:1, C.I. disperse purple 93 and C.I. disperse orange 76 with blue black is classified as forbidden dye by European countries such as Germany because C.I. disperse orange 76 can be cracked under certain specific conditions to generate arylamine harmful to human body and generate allergy to human body. In recent years, there have been many disperse blue-black dye compositions as substitutes for c.i. disperse orange 76, such as documents CN1230575A, CN101798472A, and CN105111785, etc., but there is room for further improvement in dye fastness.

Disclosure of the invention

The invention provides a blue-to-black disperse dye composition and a dye product, wherein the dye can be applied to printing and dyeing of polyester and other hydrophobic fiber materials, has the characteristics of excellent color fastness to rubbing, sublimation and washing, and is economical and environment-friendly.

The technical scheme adopted by the invention is as follows:

a blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the component D is selected from at least one of the following formulas (IV) to (V), based on the total weight of the components A to D, the mass percent of the component A is 20-85%, the mass percent of the component B is 5-50%, the mass percent of the component C is 5-60%, and the mass percent of the component D is 5-60%,

in formula (I):

X¹is Cl, Br or cyano; r¹、R²Each independently is C₁～C₄Preferably methyl or ethyl; r³、R⁴Each independently is C₁～C₄Alkyl, allyl, or by cyano, C₁～C₄Alkoxy, -COOR¹²、-OCOR¹³Substituted C₁～C₄Alkyl radical, wherein R¹²、R¹³Each independently is C₁～C₄Alkyl groups of (a);

in formula (II):

X²is Cl or Br, R⁵Is methyl, ethyl or amino, R⁶、R⁷Each independently is ethyl, propyl, isopropyl, butyl or methoxyethyl.

In the formula (III):

X³is 1 or 2C₁～C₄Alkyl radical, R⁸Is C₁～C₄Alkoxy-substituted C₁～C₄Alkyl or benzyl.

In the formula (IV):

X⁴is-SO₂NHR¹⁴，R¹⁴Is C₁～C₁₈Straight or branched alkyl of, X⁵Is hydrogen, methyl or bromine, R⁹Is C₁～C₄An alkyl group;

in formula (V):

X⁶、X⁷each independently of the other being hydrogen, halogen or nitro, R¹⁰、R¹¹One is C₁～C₄Alkyl, cyanoethyl, benzyl or phenethyl, the other is methoxycarbonylmethyl or methoxycarbonylethyl, preferably R¹⁰、R¹¹One is ethyl or benzyl and the other is methoxycarbonylmethyl.

As a further preference, the component a is one of the following formulae or a mixture of two or more thereof:

it is further preferred that component A is at least one of the formulae (I-1) to (I-4).

As a further preference, the component B is one of the following formulae or a mixture of two or more thereof:

more preferably, component B is at least one of the formulae (II-1) to (II-5).

As a further preference, the component C is one of the following formulae or a mixture of two or more thereof:

it is further preferred that component C is at least one of the formulae (III-1) to (III-5).

As a further preference, the component D is one of the following formulae or a mixture of two or more thereof:

it is further preferred that component D is at least one of the formulae (IV-1) to (IV-7) and/or the formulae (V-1) to (V-3).

Preferably, the blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D, wherein based on the total weight of the components A to D, the mass percentage of the component A is 20-85%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-60%, and the mass percentage of the component D is 5-60%.

The disperse blue to black disperse dye composition preferably comprises a component A, a component B, a component C and a component D, wherein:

component A is at least one selected from the group consisting of formulae (I-1) to (I-4),

the component B is at least one selected from formulas (II-1) to (II-5),

the component C is at least one selected from formulas (III-1) to (III-5),

the component D is selected from at least one of formulas (IV-1) to (IV-7) and/or formulas (V-1) to (V-3).

Based on the total weight of the components A to D, the mass percentage of the component A is 20-85%, the mass percentage of the component B is 5-50%, the mass percentage of the component C is 5-60%, and the mass percentage of the component D is 5-60%.

Still more preferably, the disperse blue to black disperse dye composition of the present invention is composed of component a, component B, component C and component D, wherein:

the component B is at least one selected from formulas (II-1) to (II-5),

the component C is at least one selected from formulas (III-1) to (III-5),

When the blue-to-black disperse 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 blue-to-black disperse dye product, which consists of the blue-to-black disperse dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is preferably selected from one or a mixture of more than two of the following components: naphthalenesulfonic acid-formaldehyde condensates, lignosulfonates, alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), sodium lignosulfonates (lignin 85A, lignin 83A), sodium sulfate, polycarboxylates, and the like.

The preparation method of the blue-black disperse dye product comprises the following steps:

mixing the dye monomer compounds (crude dye, dye filter cake) of the component A, the component B, the component C and the component D 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; the dye monomer compound may be further 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 blue to black disperse dye product of the present invention is liquid after being ground by a sand mill or a grinder, and can be powdery or granular after being spray-dried, which is a preparation method well known to those skilled in the art.

In the present invention, the dye compounds represented by the formulae (I) to (V) can be conveniently synthesized by diazotization and coupling methods known to those skilled in the art, and commercially available ones can also be used.

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.

When the blue-to-black disperse dye composition and the dye product provided by the invention are applied to dyeing of hydrophobic fiber materials, the blue-to-black disperse dye composition has the characteristics of excellent color fastness to rubbing, sublimation and washing, and is economical and environment-friendly.

(IV) detailed description of the preferred embodiments

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

example 1:

20 g of component A shown in formula (I-11) and formula (I-12), 10 g of component B shown in formula (II-1) and formula (II-2), 30 g of component C shown in formula (III-1), 10 g of component D shown in formula (IV-1) and 250 g of dispersing agent MF, and 1000 g of water are added for blending, grinding, dispersing and drying to obtain a finished product, wherein the dye can provide black with excellent fastness properties for polyester fabrics.

Example 2:

30 g of component A shown in formula (I-11) and formula (I-12), 10 g of component B shown in formula (II-5) and formula (II-6), 5 g of component C shown in formula (III-1), 10 g of component D shown in formula (V-1) and 250 g of dispersing agent MF are mixed with 3000 g of water, and then the mixture is ground, dispersed and dried to obtain the finished product, and the dye can provide navy blue with excellent fastness properties for polyester fabrics.

Examples 3 to 50:

according to the method described in the embodiment 1 or 2, except that the structures and the weights of the components A to D in the table 1 are adopted, 200 g of the auxiliary agent (150 g of the dispersing agent MF and 50 g of the sodium lignosulfonate) is added, 2500 g of water is added to be mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, wherein the dye can provide blue to black with excellent fastness properties for polyester fabrics.

TABLE 1

Comparative example 1

The closest example 12 of patent CN105111785A was taken as comparative example 1, and the dye composition was as follows:

comparative example 2

The closest example 1 in patent CN1230575A was taken as comparative example 2, and the dye composition was as follows:

comparative example 3

The closest example 1 in patent CN101798472A was taken as comparative example 3, and the dye composition was as follows:

comparative example 4

The closer example 9 in patent CN101798472A was taken as comparative example 4, and the dye composition was as follows:

dyeing example:

respectively weighing 2 g of the disperse dye prepared in the examples 1-50 and the dye prepared in the comparative examples 1-4, treating the polyester fabric by adopting a conventional high-temperature high-pressure dyeing method and heat setting, controlling the dyeing depth (o.w.f) to be 6.0% and the bath ratio to be 1: 25, adjusting the pH value of a dyeing bath to be 4-5, dyeing at room temperature, heating to 125 ℃ at 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing and drying according to a conventional method, and carrying out heat setting at 180 ℃ for 30 seconds to obtain the blue-to-black dyed fabric. The results of testing the fastness to rubbing, washing and sublimation according to ISO 105-X12, AATCC 61-2A, ISO 105X 11P 01 are shown in Table 2 below:

TABLE 2

In conclusion, when the blue-black disperse dye composition provided by the invention is applied to dyeing of polyester fabrics, various color fastness is excellent, and the blue-black disperse dye composition can meet the printing and dyeing requirements of various medium-high grade polyesters and blended fabrics thereof.

Claims

1. A blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the component D is selected from at least one of the following formulas (IV) to (V), based on the total weight of the components A to D, the mass percent of the component A is 20-85%, the mass percent of the component B is 5-50%, the mass percent of the component C is 5-60%, and the mass percent of the component D is 5-60%,

in formula (I):

X¹is Cl, Br or cyano; r¹、R²Each independently is C₁～C₄Alkyl of R³、R⁴Each independently is C₁～C₄Alkyl, allyl, or by cyano, C₁～C₄Alkoxy, -COOR¹²、-OCOR¹³Substituted C₁～C₄Alkyl radical, wherein R¹²、R¹³Each independently is C₁～C₄Alkyl groups of (a);

in formula (II):

X²is Cl or Br, R⁵Is methyl, ethyl or amino, R⁶、R⁷Each independently is ethyl, propyl, isopropyl, butyl or methoxyethyl;

in the formula (III):

X³is 1 or 2C₁～C₄Alkyl radical, R⁸Is C₁～C₄Alkoxy-substituted C₁～C₄Alkyl or benzyl;

in the formula (IV):

in formula (V):

X⁶、X⁷each independently of the other being hydrogen, halogen or nitro, R¹⁰、R¹¹One is C₁～C₄Alkyl, cyanoethyl, benzyl or phenethyl, and the other is methoxycarbonylmethyl or methoxycarbonylethyl.

2. The blue-to-black disperse dye composition according to claim 1, which consists of the component A, the component B, the component C and the component D.

3. A blue to black disperse dye composition according to claim 1, wherein the component A is selected from one of the following formulas or a mixture of two or more thereof in any ratio:

4. a blue to black disperse dye composition according to claim 1, wherein the component B is selected from one of the following formulas or a mixture of two or more thereof in any ratio:

5. a blue to black disperse dye composition according to claim 1, wherein the component C is selected from one of the following formulas or a mixture of two or more thereof in any ratio:

6. a blue to black disperse dye composition according to claim 1, wherein the component D is selected from one of the following formulas or a mixture of two or more thereof in any ratio:

7. the blue-to-black disperse dye composition according to claim 1, which comprises a component A, a component B, a component C and a component D, wherein:

the component B is at least one selected from formulas (II-1) to (II-5),

the component C is at least one selected from formulas (III-1) to (III-5),

the component D is selected from at least one of formulas (IV-1) to (IV-7) and/or formulas (V-1) to (V-3);

8. A disperse dye preparation comprising a blue-to-black disperse dye composition according to any one of claims 1 to 7 and an auxiliary in a weight ratio of 0.2 to 5: 1.

9. A disperse dye composition according to claim 8 wherein the auxiliary agent is one or a combination of any of the following: naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, anhydrous sodium sulphate and polycarboxylic acid polymer dispersant.

10. Use of a disperse dye preparation according to claim 9 for dyeing polyester and polyester blend fabrics.