A low-hue red disperse dye composition, and a method for preparing and using the same

Abstract

The application provides a red disperse dye composition with a low metamerism index and a preparation method and application thereof. The red disperse dye composition comprises 1-5% of C.I. Disperse Red 362, 25-50% of C.I. Disperse Red 91 and 45-70% of C.I. Disperse Red 92 in terms of mass fraction. Through the synergistic complementation of C.I. Disperse Red 362, C.I. Disperse Red 91 and C.I. Disperse Red 92 in color and spectral characteristics, the red disperse dye composition of the application is consistent with C.I. Disperse Red 60 in color and spectral characteristics, does not cause metamerism under any light source, has a very low condition metamerism index (MI) in the dyeing of textiles, and even the MI value can be ≤0.6, which meets the relevant provisions in "Textile Color System: FZ / T 01099-2021".

Description

Technical Field

[0001] This invention relates to the field of red disperse dye technology, specifically to a red disperse dye composition with a low metamerism index, its preparation method, and its application. Background Technology

[0002] CI Disperse Red 60, traded as Disperse Red 3B, Disperse Red FB or Disperse Red E-4B, has the structural formula shown in formula (VI).

[0003]

[0004] As a bright red dye with a bluish tint, CI Disperse Red 60 is widely used in the textile printing and dyeing industry. As one of the three primary colors of disperse dyes at low temperatures, CI Disperse Red 60 exhibits excellent performance in terms of leveling, enhancement, and stability. However, due to its small molecular weight (M = 331.32), CI Disperse Red 60 has significant deficiencies in sublimation fastness and heat migration resistance.

[0005] Currently, some blended products with similar colors to CI Disperse Red 60 have appeared on the market. For example, patent number CN111040469A proposes a blending scheme using CI Disperse Red 343, CI Disperse Red 362, and CI Disperse Red 60, aiming to reduce the cost of using disperse reds and meet the needs of printing and dyeing mid-to-low-end fabrics. Furthermore, patent number CN108530947B further proposes a blending scheme including CI Disperse Red 343, CI Disperse Red 362, CI Disperse Red 60, and CI Disperse Red 146 to meet market requirements for environmental protection and economy.

[0006] Although these blended products reduce costs to some extent, the spectral curves of CI Disperse Red 343 and CI Disperse Red 362, with only a single absorption peak, differ significantly in optical absorption characteristics from Disperse Red 60, which has two absorption peaks (maximum absorption wavelengths at 521 nm and 557 nm, respectively) and a smaller shoulder peak (489–502 nm). Figure 3 As shown in Figure (a), the spectral curves of the mixed dyes differ significantly from those of the original Disperse Red 60. Even at the optimal ratio, the goodness of fit R calculated using the least squares method is... n It is only 0.8928, such as Figure 3 As shown in Figure (b), this indicates that in order to mitigate metamerism, a large amount of Disperse Red 60 primary dye must be added to the blended products. As a result, the performance improvement of these products is limited, and they cannot simultaneously meet the requirements of printing and dyeing production for high sublimation fastness, high heat migration resistance, high washability, and low metamerism index. Summary of the Invention

[0007] Technical problems solved

[0008] In view of the deficiencies of the prior art, the present application provides a red disperse dye composition with low metamerism index, and a preparation method and application thereof, which solves the problems presented in the background art.

[0009] Technical solutions

[0010] To achieve the above object, the present application is implemented by the following technical solutions:

[0011] According to a first aspect of the present application, a red disperse dye composition with low metamerism index comprises, by mass fraction, 1-5% of dye A, 25-50% of dye B, and 45-70% of dye C.

[0012] The structural formula of the dye A is shown as formula (I):

[0013]

[0014] The structural formula of the dye B is shown as formula (II):

[0015]

[0016] The structural formula of the dye C is shown as formula (III):

[0017]

[0018] The present application obtains a dye composition that can replace C.I. Disperse Red 60 by blending the dye B and the dye C to obtain spectral and color characteristics close to and complementary to C.I. Disperse Red 60, the dye B being more yellow than C.I. Disperse Red 60, the dye C being more blue than C.I. Disperse Red 60, the color being slightly dark after mixing the dye B and the dye C due to subtractive color mixing, and the addition of the dye A to improve the brilliance of the composition.

[0019] Preferably, the mass fraction of the dye A in the red disperse dye composition is 1-3%, the mass fraction of the dye B in the red disperse dye composition is 30-45%, and the mass fraction of the dye C in the red disperse dye composition is 50-65%.

[0020] Preferably, the red disperse dye composition further comprises a dye D, the dye D being selected from at least one of structural formula (IV) or structural formula (V), and the mass fraction of the dye D in the red disperse dye composition being 0.5-2.5%.

[0021]

[0022] The present application plays the role of fine-tuning color by adding a small amount of dye D to the red disperse dye composition, and realizes the consistency with C.I. Disperse Red 60 in color and spectral characteristics, and the metamerism will not be caused by changing the light source arbitrarily.

[0023] Preferably, the red disperse dye composition further comprises a dispersant, and the mass fraction of the dispersant in the red disperse dye composition is 3-13%.

[0024] Preferably, the dispersant is at least one selected from naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate or sodium lignosulfonate.

[0025] Preferably, the mass ratio of the dye B to the dye C is 1:1-2.

[0026] According to the second aspect of the present application, a preparation method of the red disperse dye composition with low metamerism index is provided, which comprises sufficiently mixing and grinding dye A, dye B, dye C, dye D and a dispersant to obtain the red disperse dye composition.

[0027] Specifically, the preparation method of the red disperse dye composition with low metamerism index is selected from the following three methods.

[0028] Method one:

[0029] The solid powdery dye A, dye B, dye C and dye D are weighed according to the proportion and placed in a dye mixing kettle, a dispersant is added, and the mixing kettle is opened for stirring and mixing to obtain the red disperse dye composition.

[0030] Method two:

[0031] The dry or wet (filter cake) of the dye A, dye B, dye C and dye D is weighed according to the proportion and placed in a sand mill, water and a dispersant are added, and the sand mill is opened for grinding and dispersing, and after reaching the specified particle size, filtration and spray drying are carried out to obtain the red disperse dye composition.

[0032] Method three:

[0033] The liquid dye A, dye B, dye C and dye D are weighed according to the proportion and placed in a sand mill, a dispersant is added, and the sand mill is opened for grinding and dispersing to obtain the red disperse dye composition.

[0034] According to the third aspect of the present application, the application of the red disperse dye composition with low metamerism index to dyeing fabric is provided.

[0035] Preferably, the specific step of the dyeing is as follows: dissolving the red disperse dye composition in water to obtain a dye bath, adjusting the pH of the dye bath to 4.5-5.5 with glacial acetic acid, putting the fabric in, first heating to 80℃ at a heating rate of 3℃ / min, then heating to 130℃ at a heating rate of 1℃ / min, keeping for 30 min, finally cooling to 80℃ at a cooling rate of 2℃ / min, taking out the fabric, washing once, reducing cleaning, washing twice, and drying to obtain the dyed fabric.

[0036] (III) Beneficial effects

[0037] The present application provides a red disperse dye composition with low metamerism index and its preparation method and application. It has the following beneficial effects:

[0038] (1) The red disperse dye composition with low metamerism index provided by the present application realizes the consistency of the red disperse dye composition and C.I. Disperse Red 60 in color and spectral characteristics through the synergistic complementation of pigment A, dye B and dye C in color and spectral characteristics. It will not cause metamerism under any light source, has extremely low condition metamerism index (MI) in the dyeing of textiles, and even the MI value can be ≤0.6, which meets the relevant provisions in "Textile Color System: FZ / T01099-2021".

[0039] (2) The red disperse dye composition with low metamerism index provided by the present application has high molecular weight and molecular volume, which has excellent washing and sunlight fastness in the process of dyeing textiles. In addition, the sublimation fastness of the red disperse dye composition is significantly better than that of C.I. Disperse Red 60 original dye and other substitutes. At the same time, with the improvement of sublimation fastness and heat migration performance, the reduction of washing fastness caused by dye heat migration is also greatly weakened. BRIEF DESCRIPTION OF DRAWINGS

[0040] Figure 1 The spectral curve comparison chart of the red disperse dye composition prepared in Example 1 of the present application and C.I. Disperse Red 60;

[0041] Figure 2 The spectral curve comparison chart of the red disperse dye composition prepared in Example 2 of the present application and C.I. Disperse Red 60;

[0042] Figure 3 The spectral curve chart, wherein (a) is the spectral curve comparison chart of C.I. Disperse Red 362, C.I. Disperse Red 343 and C.I. Disperse Red 60 monomers, and (b) is the spectral curve comparison chart of the mixture of C.I. Disperse Red 362 and C.I. Disperse Red 343 and C.I. Disperse Red 60;

[0043] Figure 4 The process curve for dyeing polyester fabric with the red disperse dye composition of the present application is shown in the figure. DETAILED DESCRIPTION

[0044] The present application will be further described in conjunction with specific examples. It should be understood that these examples are only used to illustrate the present application and not used to limit the scope of the present application. Furthermore, it should be understood that after reading the content of the present application, those skilled in the art can make various modifications or changes to the present application, and these equivalent forms also fall within the scope of the present application as defined in the appended claims.

[0045] The dyes A to D and the dispersing agent in the present application are all commercially available products, and each of the dyes is in the form of liquid or solid.

[0046] The dye A can be C.I. Disperse Red 362 (CAS: 52372-36-8 / 158129-94-3) produced by Longsheng Co., Ltd., Nippon Shokubai Co., Ltd., and Gi-Ju-A Co., Ltd., etc.

[0047] The dye B can be C.I. Disperse Red 91 (CAS: 34231-26-0 / 12236-10-1) produced by Dystar, Nippon Shokubai Co., Ltd., and Wan-Fung Co., Ltd., etc.

[0048] The dye C can be C.I. Disperse Red 92 (CAS: 12236-11-2 / 72363-26-9) produced by Longsheng Co., Ltd., Nippon Shokubai Co., Ltd., and Wan-Fung Co., Ltd., etc.

[0049] The dye D can be C.I. Disperse Red 153 (CAS: 78564-87-1 / 25176-89-0 / 25150-28-1) produced by Longsheng Co., Ltd., Nippon Shokubai Co., Ltd., Wan-Fung Co., Ltd., and Gi-Ju-A Co., Ltd., etc., or C.I. Disperse Red 343 (CAS: 99031-78-6 / 68385-96-6 / 72968-82-2) produced by Longsheng Co., Ltd., Nippon Shokubai Co., Ltd., Wan-Fung Co., Ltd., and Gi-Ju-A Co., Ltd., etc.

[0050] The dispersing agent in the present application is also selected from commercially available products, and the dispersing agent is in the form of liquid or solid.

[0051] The naphthalene sulfonic acid formaldehyde condensate can be selected from commercially available dispersing agent NNO.

[0052] The methylnaphthalene sulfonic acid formaldehyde condensate can be selected from commercially available dispersing agent MF.

[0053] The sodium lignosulfonate can be selected from the commercially available dispersant Reax 85A.

[0054] Examples 1-7

[0055] The four dye monomers and the dispersant were mixed according to the mass fractions shown in Table 1, and then ground and dispersed by a sand mill to obtain a red disperse dye composition.

[0056] Table 1

[0057]

[0058] The spectral curves of Example 1 and Example 2 of the present application and the commercially available product C.I. Disperse Red 60 were compared, as shown in Figures 1 to 2 The red disperse dye composition of Example 1: dye A (red 362) + dye B (red 91) + dye C (red 92) + dye D (red 153) and the red disperse dye composition of Example 2: dye A (red 362) + dye B (red 91) + dye C (red 92) + dye D (red 343) both have two absorption peaks and one shoulder peak, and the positions and intensities of the absorption peaks are basically the same as those of C.I. Disperse Red 60, so the spectral curve shapes of the two dye compositions are consistent with that of C.I. Disperse Red 60 in the visible light range of 380-780 nm. In addition, the goodness of fit (R n ) of the spectral curves of the red disperse dye compositions of Example 1 and Example 2 relative to C.I. Disperse Red 60 is as high as 0.9939 and 0.9937, respectively, which also indicates that the red disperse dye compositions of Example 1 and Example 2 have a very high similarity to the original dye of C.I. Disperse Red 60.

[0059] Examples 8-14

[0060] The four dye monomers, the dispersant and water were placed in a sand mill according to the mass fractions shown in Table 2, and then ground and dispersed, followed by filtration and spray drying to obtain a red disperse dye composition.

[0061] Table 2

[0062]

[0063] Examples 15-18

[0064] The four monomers were placed in a sand mill according to the mass fractions shown in Table 3, and then the dispersant was added as needed, and the sand mill was started to grind and disperse sufficiently to obtain a red disperse dye composition.

[0065] Table 3

[0066]

[0067]

[0068] Test examples 1-18

[0069] Respectively, 0.2g of the red disperse dye composition prepared in examples 1 to 18 was placed in a 100ml volumetric flask, and water was added to the calibration mark to prepare a mother liquor with a concentration of 2g / L. 20ml of the mother liquor was taken with a pipette and placed in a dye cup, and 20ml of water was added to prepare a dye bath. The pH value of the dye bath was adjusted to 4.5-5.5 with glacial acetic acid, then 4g of polyester fabric was placed in it, and dyeing was carried out according to the process curve shown in the figure. After completion, the fabric was taken out, washed with water, reduced and washed (sodium hydrosulfite 2g / L, sodium hydroxide 1g / L, bath ratio 1:30, 65℃×10min), then washed with water, and dried at 80℃ to obtain dyed fabric. Figure 4

[0070] The color difference (DE), conditional isochromatic index (MI) and color fastness of the dyed fabric dyed with the red disperse dye composition of examples 1 to 18 were tested, wherein the color fastness was tested according to the methods of national standards GB / T 3921.C3-2013, GB / T 5718-2008 (180℃, 30s), GB / T 8427-2013 (20h) for water washing resistance, sublimation resistance and sunlight resistance, respectively, and the test results are shown in Table 4.

[0071] Table 4

[0072]

[0073]

[0074] From the test results in Table 4, it can be seen that the water washing resistance level of the dyed polyester fabric with the red disperse dye composition of the present application is 4-5, the sublimation resistance level is 4-5, the sunlight resistance level is 6-7, and the MI value of the color difference test result is less than 0.6. It is proved that the red disperse dye composition provided by the present application has excellent color fastness and does not have metamerism phenomenon.

[0075] Although the embodiments of the present application have been shown and described, it will be understood by those of ordinary skill in the art that various changes, modifications, substitutions and alterations can be made without departing from the principles and spirit of the present application, and the scope of the present application is defined by the appended claims and their equivalents.​

Claims

1. A low-hue red disperse dye composition characterized in that: 1-5% of dye A, 25-50% of dye B and 45-70% of dye C by mass fraction; The structural formula of the dye A is shown as formula (I): ； The structural formula of the dye B is shown as formula (II): ； The structural formula of the dye C is shown as formula (III): 。 2. A low-hue red disperse dye composition according to claim 1, characterized in that: The mass fraction of the dye A in the red disperse dye composition is 1-3%, the mass fraction of the dye B in the red disperse dye composition is 30-45%, and the mass fraction of the dye C in the red disperse dye composition is 50-65%.

3. A low-hue red disperse dye composition according to claim 1, characterized in that: The red disperse dye composition further comprises a dye D selected from at least one of formula (IV) or formula (V), and the mass fraction of the dye D in the red disperse dye composition is 0.5-2.5%. ； 。 4. A low-hue red disperse dye composition according to claim 1, characterized in that: The red disperse dye composition further comprises a dispersant, and the mass fraction of the dispersant in the red disperse dye composition is 3-13%.

5. A low-hue red disperse dye composition according to claim 4, characterized in that: The dispersant is selected from at least one of naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate or sodium lignosulfonate.

6. A low-hue red disperse dye composition according to claim 1, characterized in that: The mass ratio of the dye B to the dye C is 1:1-2.

7. Use of the low-hue-angle red disperse dye composition according to any one of claims 1-6 for dyeing a fabric.

8. Use according to claim 7, characterized in that: The specific steps of the dyeing are as follows: dissolving the red disperse dye composition in water to obtain a dye bath, adjusting the pH of the dye bath to 4.5-5.5 with glacial acetic acid, putting the fabric in the dye bath, first heating to 80°C at a heating rate of 3°C / min, then heating to 130°C at a heating rate of 1°C / min, keeping the temperature for 30 min, finally cooling to 80°C at a cooling rate of 2°C / min, taking out the fabric, washing once, reducing cleaning, washing twice, and drying to obtain the dyed fabric.

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