Dark red disperse dye

Abstract

The present invention provides a dark red disperse dye, which comprises a dye composition and an auxiliary agent, the weight ratio of the dye composition to the auxiliary agent is 1: 0.5-5, and the dye composition comprises the following components by weight: 35-85% of a component A composed of one or two of compounds represented by a formula (I); 5-40% of a component B composed of a compound represented by a formula (II); the component C is composed of one or two of the compounds shown in the formula (III), and the auxiliary agent is selected from one or a mixture of more of a dispersing agent, a dispersing agent and a surfactant. # imgabs0 # wherein X is chlorine or bromine, # imgabs1 # imgabs2 # wherein R and R'are each independently a methyl group or a benzyl group and are different.

Description

Technical Field

[0001] The application relates to a dark red disperse dye, which is a dark red disperse dye with high color fastness used for dyeing and printing of polyester fiber textiles (fabrics). Background Art

[0002] Disperse dyes are a type of hydrophobic dyes with a simple molecular structure and no ionizable water-soluble groups. They are mainly used for dyeing and printing polyester fibers and their blended fabrics. They can also be used for dyeing textiles such as acetate fibers and polyamide fibers. Deep red is one of the main color systems of disperse dyes. In recent years, disperse dyes with excellent lifting power and high color fastness have gradually increased their share of the dye market. They are particularly suitable for sportswear fabrics and travel clothing fabrics that have high requirements for dye performance. Since this type of clothing fabric is mostly made of polyester fiber materials, and has relatively high requirements for the comprehensive color fastness of dyes (including washing fastness, sublimation fastness, perspiration fastness, water fastness, sunlight fastness, etc.).

[0003] At present, the dark red dyes used in the dyeing of the above-mentioned sportswear fabrics and travel clothing fabrics on the market are mainly compounds shown in formula (D1) or (D2), and compounds shown in formula (D3) are also used in small quantities. Although disperse dyes containing compounds shown in formula (D1), formula (D2) or formula (D3) have excellent dyeing properties and high color fastness, their water fastness is poor (D2 and D3 are worse than D1), and there is still room for improvement in dyeing lifting power and color fastness to water stains and perspiration. Therefore, it is necessary to develop a dark red dye with excellent comprehensive fastness, which can not only meet the standard color fastness test requirements, but also pass the simple evaluation operation of water fastness.

[0004]

[0005] Summary of the invention

[0006] In view of the shortcomings of crimson dyes in the prior art, the purpose of the present invention is to provide a crimson disperse dye, which has excellent dyeing application performance, can obtain good dyeing depth and dyeing lifting power on polyester fabrics (cloths) and polyester-spandex (polyester and spandex blended) fabrics (cloths), and has excellent color fastness, such as washing fastness, sublimation fastness, perspiration fastness, water fastness, water fastness, water fastness, etc. To achieve the purpose of the present invention, the present invention adopts the following technical solutions:

[0007] A deep red disperse dye, which consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.5-5.

[0008] The dye composition comprises the following components by weight:

[0009] Component A consisting of one or two of the compounds represented by formula (I), 35% to 85%;

[0010] Component B composed of the compound represented by formula (II), 5% to 40%;

[0011] Component C composed of one or two of the compounds represented by formula (III) 5% to 40%,

[0012] Wherein X is chlorine or bromine,

[0013]

[0014] Wherein R and R' are each independently methyl or benzyl and are different

[0015] The auxiliary agent is selected from a mixture of one or more of a dispersant, a diffuser and a surfactant.

[0016] In another preferred embodiment, the auxiliary agent is selected from a dispersant, and the dispersant is selected from naphthalenesulfonic acid formaldehyde condensate, lignin sulfonate, alkylnaphthalenesulfonic acid formaldehyde condensate, methylnaphthalenesulfonic acid formaldehyde condensate, or a combination thereof.

[0017] In another preferred embodiment, the surfactant is selected from EO-based nonionic surfactants.

[0018] In another preferred embodiment, in the crimson disperse dye, the component A is composed of the compound represented by formula (I-1), and the component C is composed of the compound represented by formula (III-1), or the component C is composed of the compound represented by formula (III-2), or the component C is composed of a mixture of the compound represented by formula (III-1) and the compound represented by formula (III-2),

[0019]

[0020] In another preferred embodiment, in the crimson disperse dye, the component A is composed of the compound represented by formula (I-2), and the component C is composed of the compound represented by formula (III-1), or the component C is composed of the compound represented by formula (III-2), or the component C is composed of a mixture of the compound represented by formula (III-1) and the compound represented by formula (III-2),

[0021]

[0022] In another preferred embodiment, in the crimson disperse dye, the component A is composed of a compound represented by formula (I-2) and a mixture of a compound represented by formula (I-2), and the component C is composed of a compound represented by formula (III-1), or the component C is composed of a compound represented by formula (III-2), or the component C is composed of a mixture of a compound represented by formula (III-1) and a compound represented by formula (III-2),

[0023]

[0024] In another preferred example, in the crimson disperse dye, the weight ratio of the dye composition to the auxiliary agent is 1:0.6-2.5.

[0025] In another preferred embodiment, in the dye composition, the weight content of component A composed of the compound represented by formula (I) is 40% to 80%.

[0026] In another preferred embodiment, in the dye composition, the weight content of component B composed of the compound represented by formula (II) is 7% to 35%.

[0027] In another preferred embodiment, in the dye composition, the weight content of component C composed of the compound represented by formula (III) is 7% to 35%.

[0028] In another preferred embodiment, the crimson dye composition provided by the present invention consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.6-2.

[0029] The dye composition is composed of the following components in percentage:

[0030] Component A of the compound represented by formula (I-1) 40% to 63%,

[0031] Component B composed of the compound represented by formula (II) 12% to 25%,

[0032] Component C of the compound represented by formula (III-1) is 12% to 35%,

[0033] The auxiliary agent is methylnaphthalenesulfonic acid formaldehyde condensate.

[0034] In another preferred embodiment, the crimson dye composition provided by the present invention consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.8-1.5.

[0035] Component A composed of the compound represented by formula (I-1) and the compound represented by formula (I-2) 56% to 80%,

[0036] Component B composed of the compound represented by formula (II) 7% to 35%,

[0037] The dye composition represented by formula (III-2) comprises 7% to 25% of component C.

[0038] The auxiliary agent is lignin or a mixture of lignin and methylnaphthalenesulfonic acid formaldehyde condensate,

[0039] In component A, the weight ratio of the compound represented by formula (I-1) to the compound represented by formula (I-2) is 3.0 to 0.8:1, and

[0040] In the mixture of lignin and methylnaphthalenesulfonic acid formaldehyde condensate, the weight ratio of lignin to methylnaphthalenesulfonic acid formaldehyde condensate is 1:2-5.

[0041] In another preferred embodiment, the crimson dye composition provided by the present invention consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.8-2.0:

[0042] Component A of the compound represented by formula (I-2) 50% to 60%,

[0043] Component B composed of the compound represented by formula (II) 15% to 25%,

[0044] Component C composed of the dye represented by formula (III-1) and the dye represented by formula (III-2) 20% to 30%,

[0045] The auxiliary agent is composed of methylnaphthalenesulfonic acid formaldehyde condensate and lignin.

[0046] In component C, the weight ratio of the compound represented by formula (III-1) to the compound represented by formula (III-2) is 2 to 0.5:1, and

[0047] In the auxiliary agent, the weight ratio of methylnaphthalenesulfonic acid formaldehyde condensate to lignin is 2-6:1.

[0048] In another preferred embodiment, the dark red dye composition provided by the present invention is composed of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:1.5 to 2.5.

[0049] Component A of the compound represented by formula (I-2) 45% to 62%,

[0050] Component B composed of the compound represented by formula (II) 20% to 32%,

[0051] Component C of the dye composition represented by formula (III-1) 15% to 25%,

[0052] The auxiliary agent is composed of methylnaphthalenesulfonic acid formaldehyde condensate and lignin.

[0053] In the auxiliary agent, the weight ratio of methylnaphthalenesulfonic acid formaldehyde condensate to lignin is 12-6:1.

[0054] The present invention also provides a method for using the crimson disperse dye, comprising mixing the crimson disperse dye with water, grinding and dispersing the mixture, and then spray drying the mixture to form a powder or granular disperse dye. The mixture may also be prepared into a liquid disperse dye without drying. DETAILED DESCRIPTION

[0055] In view of the defects of crimson dyes in the prior art, the inventors of the present application considered that under the premise of not significantly affecting the dyeing property of disperse dyes, several dyes were selected for optimization combination by appropriately increasing the molecular weight of the dyes, adding electron-withdrawing groups, introducing hydrophobic planar structures, etc. After in-depth research, it was found that a crimson disperse dye has a good dyeing effect on polyester and polyester-spandex fabrics. The crimson disperse dye contains component A composed of one or two of the compounds shown in formula (I), component B composed of the compounds shown in formula (II), and component C composed of one or two of the compounds shown in formula (III). The crimson disperse dye is used for dyeing and printing of hydrophobic fiber textiles, especially textiles containing polyester fibers (such as polyester fabrics and polyester-spandex fabrics). The obtained dyed fabric has the advantages of high dyeing rate, good dyeing depth, excellent lifting power, excellent color fastness, good leveling property, etc.

[0056] The preparation of the compound represented by formula (I) and the compound represented by formula (II) of the present invention can be carried out with reference to EP 0555179 A1.

[0057] The compound represented by formula (III-1) is CAS 2093329-85-0, and the compound represented by formula (III-2) is CAS 1613451-37-8.

[0058] In the dark red disperse dye of the present invention, the auxiliary agent includes but is not limited to a dispersant, a diffusing agent, and a surfactant.

[0059] The dispersant is a commonly used dispersant in disperse dyes, such as naphthalenesulfonic acid formaldehyde condensate, lignin sulfonate, alkylnaphthalenesulfonic acid formaldehyde condensate, methylnaphthalenesulfonic acid formaldehyde condensate, etc. The methylnaphthalenesulfonic acid formaldehyde condensate used is a commonly used dispersant in the art, for example, CAS 9084-06-4.

[0060] The diffusing agent is a commonly used dispersing agent in disperse dyes.

[0061] The surfactant is a surfactant commonly used in disperse dyes.

[0062] The compound represented by formula (I) of the present invention adds an electron-withdrawing group -Cl or -Br on the basis of the compound represented by formula (II) (i.e., the compound represented by the above-mentioned existing crimson dye formula (D1)), thereby producing a dark color effect and a rich color effect; the hydrophobic planar structure introduced into the compound represented by formula (III) increases the hydrophobicity of the dye molecules and enhances the coplanarity, which helps to enhance the dispersion stability of the dye in water, improve the affinity of the dye for hydrophobic fibers, improve the dyeing depth of the dye, and obtain excellent dye lifting power.

[0063] In the description of the present invention, "cloth", "fabric" and "textile" can be used interchangeably.

[0064] Compared with the existing crimson dyes, the crimson disperse dyes of the present invention have the following advantages: compared with the dyes of the compounds of formula (D1), the compounds of formula (I) of the present invention have an electron-withdrawing group -Cl or -Br, which increases the molecular weight of the dye and increases the difficulty of the dye molecules diffusing from the inside of the fiber to the outside under high temperature and high humidity conditions, thereby helping to improve the light fastness, sublimation fastness, washing fastness and water fastness of the dye. The compounds of formula (III) have multiple benzene rings and heterocycles in their molecular structure, which enhance the coplanarity and hydrophobicity of the dye molecules, not only improving the lifting power of the dye, but also helping to improve the light fastness, sublimation fastness, washing fastness and water fastness of the dye.

[0065] The present invention is further illustrated by the following examples, but the present invention is not limited thereto. Unless otherwise specified, the raw materials and reagents used in the following examples are commercially available; experimental methods without specific conditions are usually carried out under conventional conditions or under conditions recommended by the manufacturer.

[0066] Embodiment 1:

[0067] Mix 25.0 g of dye component A represented by formula (I-1), 7.5 g of dye component B represented by formula (II), 7.5 g of dye component C represented by formula (III-1), and 65.0 g of methylnaphthalenesulfonic acid formaldehyde condensate (as a dispersant, abbreviated as "MF"), add 158.0 g of water and grind and disperse in a sand mill, and spray dry to obtain a deep red disperse dye product.

[0068] Embodiments 2 to 8:

[0069] Referring to the method of Example 1, the dyes of Examples 2 to 8 were prepared, and the amounts of the components used were as shown in Table 1.

[0070] Table 1

[0071]

[0072]

[0073] Comparative Example 1

[0074] 40.0 g of the dark red dye of the compound represented by formula (II) was taken separately, mixed with 65.0 g of dispersant MF, added with 158.0 g of water, ground and dispersed in a sand mill, and spray-dried to obtain a finished dark red disperse dye (see Table 1).

[0075] The dark red disperse dye products prepared in Examples 1 to 8 and Comparative Example 1 were respectively taken and the polyester fabric was subjected to exhaust dyeing at 130°C, the holding time was 50 minutes, the dyeing concentration was 0.5% to 4% (owf), and the dyeing bath ratio was 20:1. After dyeing, reduction cleaning was performed at 90°C for 20 minutes. The lifting power of the dyes of Examples 1 to 8 and Comparative Example 1 was measured and evaluated according to GB / T 2397-2012, and the results are shown in Table 2.

[0076] Table 2 Dyeing lifting power of dyes on polyester fabrics

[0077] Example Lifting force 1 excellent 2 excellent 3 excellent 4 good 5 excellent 6 excellent 7 good 8 excellent Comparative Example generally

[0078] The dark red dyes of Examples 1 to 8 and Comparative Example 1 were used to perform exhaust dyeing on polyester fabrics at 130°C, with a holding time of 50 minutes and a dyeing bath ratio of 20:1. The dyeing concentration of the dye of Comparative Example 1 was 2% (owf), and the dyeing concentrations of the dyes of Examples 1 to 8 are listed in Table 3, and substantially the same dyeing depth as that of the dye of Comparative Example 1 was obtained. After dyeing, reduction cleaning was performed at 90°C for 20 minutes.

[0079] The dyed fabric samples were heat-set at 180°C for 30 seconds, and then the washing resistance, water stain resistance, perspiration resistance, chlorinated water resistance, light fastness and sublimation fastness of the dyed fabrics were tested according to AATCC 61-2A, GB / T5713-2013, GB / T 3922-2013, GB / T 8433-2013, GB / T 8427-2019 and GB / T 5718-1997, respectively.

[0080] The color fastness to water immersion of the dyes of Examples 1 to 8 and Comparative Example 1 was tested: the dyed fabric was heat-set at 150°C for 30 seconds, and then the heat-set dyed fabric was placed in water containing 5g / L washing powder, with a bath ratio of 1:30, and kept at 70°C for 5 minutes. The dyed fabric was taken out and the color of the water was observed and rated, with 1 being the worst and 5 being the best.

[0081] The color fastness test results of polyester fabrics are shown in Table 3.

[0082] Table 3 Color fastness of polyester fabrics

[0083]

[0084] It can be seen from the dyeing lifting power of polyester fabric in Table 2 and the dyeing fastness data in Table 3 that the dark red disperse dye of the present invention has better lifting power than the dye of Comparative Example 1; the various fastness properties of the dark red disperse dye of the present invention are similar to or better than those of the dye of the Comparative Example, especially the water fastness of the former is significantly better than that of the latter.

[0085] Referring to the dyeing method of polyester fabric, the dark red disperse dyes prepared in Examples 1 to 8 were used to perform dip dyeing on polyester-spandex fabrics (fiber weight content: polyester 85%, spandex 15%), and the lifting force was measured. The results are shown in Table 4.

[0086] Table 4 Dyeing lifting power of dyes on polyester-spandex fabrics

[0087] Example Lifting force 1 excellent 2 excellent 3 excellent 4 good 5 excellent 6 excellent 7 good 8 excellent Comparative Example 1 generally

[0088] The polyester-spandex fabrics were dip-dyed with the dyes of Examples 1 to 8 and Comparative Example 1, and the color fastnesses were shown in Table 5. The color fastnesses of the dyed fabrics were tested, and the test results were shown in Table 5.

[0089] Table 5 Color fastness of polyester-spandex fabrics

[0090]

[0091] From the dyeing lifting power and dyeing fastness data of polyester-spandex fabrics in Tables 4 and 5, it can be seen that the dark red disperse dyes prepared in Examples 1 to 8 of the present invention have better lifting power than the dyes in Comparative Example 1. The fastness properties of the dark red disperse dyes prepared in Examples 1 to 8 are similar to or better than those of the dyes in Comparative Example 1, especially the water fastness of the former is significantly better than that of the latter.

[0092] All documents mentioned in the present invention are cited as references in this application, just as each document is cited as reference individually. In addition, it should be understood that after reading the above teachings of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the claims attached to this application.

Claims

1. A deep red disperse dye, characterized in that It consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.5-5. The dye composition comprises the following components by weight: Component A consisting of one or two of the compounds represented by formula (I), 35% to 85%; Component B composed of the compound represented by formula (II), 5% to 40%; Component C composed of one or two of the compounds represented by formula (III) 5% to 40%, Wherein X is chlorine or bromine, Wherein R and R' are each independently methyl or benzyl and are different from each other; wherein the auxiliary agent is selected from a mixture of one or more of a dispersant, a diffuser and a surfactant.

2. The dark red disperse dye according to claim 1, characterized in that The auxiliary agent is selected from a dispersant, and the dispersant is selected from naphthalenesulfonic acid formaldehyde condensate, lignin sulfonate, alkylnaphthalenesulfonic acid formaldehyde condensate, methylnaphthalenesulfonic acid formaldehyde condensate, or a combination thereof.

3. The dark red disperse dye according to claim 1 or 2, characterized in that The component A is composed of the compound represented by formula (I-1), and The component C is composed of the compound represented by formula (III-1), or the component C is composed of the compound represented by formula (III-2), or the component C is composed of a mixture of the compound represented by formula (III-1) and the compound represented by formula (III-2), 4. The dark red disperse dye according to claim 1 or 2, characterized in that The component A is composed of the compound represented by formula (I-2), and The component C is composed of the compound represented by formula (III-1), or the component C is composed of the compound represented by formula (III-2), or the component C is composed of a mixture of the compound represented by formula (III-1) and the compound represented by formula (III-2), 5. The dark red disperse dye according to claim 1 or 2, characterized in that The component A is composed of a compound represented by formula (I-2) and a mixture of a compound represented by formula (I-2), and The component C is composed of the compound represented by formula (III-1), or the component C is composed of the compound represented by formula (III-2), or the component C is composed of a mixture of the compound represented by formula (III-1) and the compound represented by formula (III-2), 6. The dark red disperse dye according to claim 1 or 2, characterized in that The weight ratio of the dye composition to the auxiliary agent is 1:0.6-2.5, and / or In the dye composition, The weight content of component A of the compound represented by formula (I) is 40% to 80%, and / or The weight content of component B composed of the compound represented by formula (II) is 7% to 35%, and / or The weight content of component C composed of the compound represented by formula (III) is 7% to 35%.

7. A deep red disperse dye, characterized in that It consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.6-2. The dye composition is composed of the following components in percentage: Component A of the compound represented by formula (I-1) 40% to 63%, Component B of the compound represented by formula (II) is 12% to 25%, The component C of the compound represented by formula (III-1) is 12% to 35%, The auxiliary agent is methylnaphthalenesulfonic acid formaldehyde condensate.

8. A deep red disperse dye, characterized in that The invention is composed of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1: 0.8～1.5， Component A composed of the compound represented by formula (I-1) and the compound represented by formula (I-2) 56% to 80%, Component B composed of the compound represented by formula (II) 7% to 35%, The dye composition represented by formula (III-2) comprises 7% to 25% of component C. The auxiliary agent is lignin or a mixture of lignin and methylnaphthalenesulfonic acid formaldehyde condensate, In component A, the weight ratio of the compound represented by formula (I-1) to the compound represented by formula (I-2) is 3.0 to 0.8:1, and In the mixture of lignin and methylnaphthalenesulfonic acid formaldehyde condensate, the weight ratio of lignin to methylnaphthalenesulfonic acid formaldehyde condensate is 1:2-3.

9. A deep red disperse dye, characterized in that The invention is composed of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:0.8-2.0: Component A of the compound represented by formula (I-2) 50% to 60%, Component B of the compound represented by formula (II) is 15% to 25%, Component C composed of the dye represented by formula (III-1) and the dye represented by formula (III-2) 20% to 30%, The auxiliary agent is composed of methylnaphthalenesulfonic acid formaldehyde condensate and lignin. In component C, the weight ratio of the compound represented by formula (III-1) to the compound represented by formula (III-2) is 2 to 0.5:1, and In the auxiliary agent, the weight ratio of methylnaphthalenesulfonic acid formaldehyde condensate to lignin is 2-6:

1.

10. A deep red disperse dye, characterized in that: It consists of a dye composition and an auxiliary agent, wherein the weight ratio of the dye composition to the auxiliary agent is 1:1.5-2.5 Component A of the compound represented by formula (I-2) 45% to 62%, Component B composed of the compound represented by formula (II) 20% to 32%, The dye composition represented by formula (III-1) contains 15% to 25% of component C. The auxiliary agent is composed of methylnaphthalenesulfonic acid formaldehyde condensate and lignin. In the auxiliary agent, the weight ratio of the methylnaphthalenesulfonic acid formaldehyde condensate to the lignin is 12-6:1.

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