A red dye derivative and its application in a high-temperature direct-injection red disperse dye ink

Abstract

The present invention relates to the field of disperse dye inks, and particularly to a red dye derivative and its application in high-temperature direct-injection red disperse dye inks. A red dye derivative, the red dye derivative is shown as Formula I. The present invention provides a derivative of a red dye as a dispersant. The structure of this dispersant is similar to that of the dye, and it can bind to the dye better by van der Waals forces. The water-soluble groups therein can enhance the dispersibility of the dye in water. When the obtained derivative of the red dye is added as a dispersant to the red disperse dye ink, it will not affect the final color of the ink, and the amount of auxiliary agent used is small, the ink system has high stability and good fluidity.

Description

Technical Field

[0001] The present invention relates to the field of disperse dye inks, and specifically relates to a red dye derivative and its application in high-temperature direct-injection red disperse dye inks. Background Art

[0002] China is a major country in the textile printing and dyeing industry, with a huge demand for dyes and pigments. As a type of dye, disperse dyes are often made into disperse dye inks for application. Therefore, during the processes of preparation, transportation, storage, and use, high requirements are placed on the stability and fluidity of disperse dye inks. Generally speaking, in order to ensure the performance of the ink, various additives are often added, such as dispersants, surfactants, defoamers, preservatives, penetrants, pH regulators, and leveling agents, etc. However, adding too many of these additives may affect the final use effect of the ink and also increase the cost. Therefore, there is a need for a disperse dye ink with fewer additives and better ink stability and printing fluidity. Patent CN113832743 uses the addition of solvents with different boiling points to improve the moisture retention and fluidity of the ink, but does not explain the stability of the ink; Patent JP2021080374 adds a large equivalent of dispersant to the ink, improving the stability of the ink, but a large equivalent of dispersant is disadvantageous to the use effect of the ink. Previously, Patent CN113914116 proposed a self-made derivative dispersant with an azo structure, and adding a small amount can solve the stability problem of dyes in the ink. However, due to the color difference between the self-made derivative dispersant and some dyes, it will have a slight impact on the use effect of the ink. Summary of the Invention

[0003] The object of the present invention is to provide a high-temperature direct-injection red disperse dye ink and its preparation and application.

[0004] To solve the above problems, the present invention provides the following technical solutions:

[0005] A red dye derivative, characterized in that: the red dye derivative is shown as Formula I,

[0006]

[0007] In the formula, R1 and R2 are the same or different and are selected from hydrogen, C1-C4 alkyl, hydroxyethyl, cyanoethyl, methylsulfonyl, formyl, or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxylic acid group, or sulfonic acid group, and n is an integer from 1 to 3;

[0008] R3 is hydrogen, C1-C4 alkyl, hydroxy, amino, halogen, formamide group, acetamide group, propionamide group, methylsulfonamide group, or the group -NH(CH2) m-Y, where Y is a carboxyl group or a sulfonic acid group, and m is an integer from 1 to 3;

[0009] R4 and R5 are the same or different and are each independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, cyano, carboxyl group or sulfonic acid group;

[0010] R6 is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, halogen, cyano, methyl formate group, carboxyl group, sulfonic acid group or phosphoric acid group;

[0011] And at least one of R1-R6 contains a carboxyl group or a sulfonic acid group.

[0012] Preferably, in the formula of the red dye derivative,

[0013] R1 is selected from hydrogen, C1-C4 alkyl, cyanoethyl or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxyl group or sulfonic acid group, and n is an integer from 1 to 3;

[0014] R2 is selected from hydrogen, C1-C4 alkyl, cyanoethyl and the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxyl group or sulfonic acid group, and n is an integer from 1 to 3;

[0015] R3 is selected from hydrogen, chlorine, acetamido, propionamido, methanesulfonamido or the group -NH(CH2) m -Y, where Y is a carboxyl group or a sulfonic acid group, and m is an integer from 1 to 3;

[0016] R4 and R5 may be the same or different and are each independently selected from hydrogen, chlorine, bromine, cyano, carboxyl group or sulfonic acid group;

[0017] R6 is selected from methyl, nitro, carboxyl group and sulfonic acid group;

[0018] And at least one of R1-R6 contains a carboxyl group or a sulfonic acid group.

[0019] More preferably, in the formula of the red dye derivative,

[0020] R1 and R2 are the same or different and are each independently selected from C1-C4 alkyl, cyanoethyl or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxyl group or sulfonic acid group, and n is an integer from 1 to 3;

[0021] R3 is selected from hydrogen, chlorine, propionamido, methanesulfonamido or the group -NH(CH2) m -Y, where Y is a carboxyl group or a sulfonic acid group, and m is an integer from 1 to 3;

[0022] R4 and R5 are independently selected from hydrogen, chlorine, bromine or cyano;

[0023] R6 is selected from methyl, nitro, carboxyl and sulfonic acid groups;

[0024] And at least one of R1 - R6 contains a carboxyl group or a sulfonic acid group.

[0025] Use of a red dye derivative as defined above, the use of the red dye derivative as a dispersant in a high-temperature direct-injection red disperse dye ink.

[0026] A disperse dye ink, by weight, 2% - 20% of red dye, 0.05% - 2% of the red dye derivative as claimed in claim 1, 0.01% - 1% of surfactant, 0.01% - 1% of preservative, 15% - 40% of water-soluble organic solvent and the balance deionized water.

[0027] The disperse red dye is a disperse red dye containing an azo structure; the disperse red dye containing an azo structure is one or more of C.I. Disperse Red 7, C.I. Disperse Red 12, C.I. Disperse Red 21, C.I. Disperse Red 43, C.I. Disperse Red 56, C.I. Disperse Red 65, C.I. Disperse Red 72, C.I. Disperse Red 73, C.I. Disperse Red 82, C.I. Disperse Red 90, C.I. Disperse Red 97, C.I. Disperse Red 109, C.I. Disperse Red 113, C.I. Disperse Red 118, C.I. Disperse Red 129, C.I. Disperse Red 134, C.I. Disperse Red 167, C.I. Disperse Red 167:1, C.I. Disperse Red 173, C.I. Disperse Red 179, C.I. Disperse Red 188, C.I. Disperse Red 193, C.I. Disperse Red 197, C.I. Disperse Red 210, C.I. Disperse Red 227, C.I. Disperse Red 278, C.I. Disperse Red 311, C.I. Disperse Red 323 and C.I. Disperse Red 343.

[0028] The surfactant is one or more of a cationic surfactant, anionic surfactant, amphoteric surfactant and nonionic surfactant. Preferably, the surfactant is an anionic surfactant and / or a nonionic surfactant; more preferably, one or more of 3,6 - dimethyl - 4 - octyne - 3,6 - diol, 2,5 - dimethyl - 3 - hexyne - 3,5 - diol, 2,4,7,9 - tetramethyl - 5 - decyne - 4,7 - diol, sodium dodecyl sulfate, sodium dodecylbenzenesulfonate, sodium N - lauroylsarcosinate, Surfynol 1465, CT - 131, Disperbyk 2012, YusFS 3000, etc.

[0029] The preservative may be one or more of chlorocresol, 1,2-benzisothiazol-3-one, 2-methyl-4-isothiazolin-3-one, sym-triazine, methylene bisthiocyanate; preferably 1,2-benzisothiazol-3-one and / or 2-methyl-4-isothiazolin-3-one.

[0030] The water-soluble organic solvent may be alcohol and / or alcohol ether. The water-soluble organic solvent is one or more of ethanol, ethylene glycol, isopropanol, 1,2-propanediol, 1,3-propanediol, glycerol, ethylene glycol monomethyl ether, diethylene glycol, diethylene glycol monomethyl ether, propylene glycol monomethyl ether.

[0031] Advantages of the present invention:

[0032] The present invention provides a derivative of a red dye as a dispersant. The structure of the dispersant is similar to that of the dye, and it can combine with the dye better by van der Waals force. The water-soluble groups therein can enhance the dispersibility of the dye in water; when the obtained derivative of the red dye is used as a dispersant and added to the red disperse dye ink, it will not affect the final color of the ink, and the amount of additives used is small, the ink system has high stability and good fluidity. Specific embodiments

[0033] The following examples are for further illustration of the present invention. It should be noted that the specific embodiments described herein are only for explaining and interpreting the present invention and are not limited to the present invention.

[0034] The present invention provides a derivative of a red dye. As a derivative dispersant, the red derivative can be prepared by a diazo coupling reaction from formulas a and b:

[0035]

[0036] Among them, the substituents are described as above.

[0037] The reagents and drugs used in the present invention are all commercially available without special instructions.

[0038] Example 1

[0039] Synthesis of red derivative 1

[0040] Preparation of diazonium salt

[0041] Add 2.65 g of 4-methyl-2,6-dibromoaniline, 30 mL of water and 2.53 g of hydrochloric acid into a 150 mL three-necked flask. Use an ice-water bath to keep the temperature at 0 - 5 °C. Dissolve 0.70 g of NaNO₂ in 6 mL of water. After cooling, gradually add it dropwise into the above solution, controlling the temperature at 0 - 5 °C. After the addition is complete, continue stirring for 30 min. Test with starch potassium iodide test paper. If the test paper turns blue, it indicates that the reaction is complete; otherwise, a small amount of sodium nitrite needs to be added and the above test operation is repeated to obtain the corresponding diazo component.

[0042] Coupling reaction

[0043] Add 4.30 g of 3-(N,N-di-(3-sulfopropyl))aminomethanesulfonanilide into 30 mL of water and stir to prepare the coupling component. Then cool it to 0 - 5 °C and slowly add the diazo component. Control the pH at 4 - 6 by adding sodium acetate and ensure the temperature is at 0 - 5 °C. Continue stirring for 2 h and use H-acid to detect whether the reaction reaches the end point. After the reaction is completed, adjust the pH to about 7 with 5% sodium hydroxide solution, filter, collect the filtrate and remove the solution by rotary evaporation, and then purify to remove salts to obtain Intermediate 1 as shown in the following formula.

[0044]

[0045] Among them, 3-(N,N-di(3-sulfopropyl))aminomethanesulfonanilide can be prepared according to the method used in the literature US2019048196.

[0046] Preparation of red derivative 1 by cyanation

[0047] Add 40 mL of DMF and 0.20 g of sodium bromide into a 150 mL three-necked flask, heat up to 80 °C, slowly add 6.23 g of Intermediate 1, stir to dissolve it, and then add a total of 1.81 g of cuprous cyanide in small portions. Keep the temperature and stir for 2 h, then heat up to 120 °C and continue the reaction for 3 h. After the heat preservation is completed, cool down to 50 °C, add 30 mL of methanol dropwise, continue stirring for 1 h, add 3.20 g of sodium thiosulfate, stir for 2 h, then filter, collect the filtrate, and after rotary evaporation, purify it with an organic solvent to obtain red derivative 1 as shown in the following formula

[0048]

[0049] ( 11H NMR (500 MHz, Chloroform-d) δ 9.01 (s, 1H), 7.68 (s, 2H), 7.56 (d, J = 7.2 Hz, 1H), 6.95 (d, J = 1.9 Hz, 1H), 6.45 (dd, J = 7.2, 1.9 Hz, 1H), 3.41 (t, J = 7.1 Hz, 4H), 3.07 - 2.96 (m, 6H), 2.05 (tt, J = 10.9, 7.0 Hz, 4H)).

[0050] Example 2

[0051] Synthesis of Red Derivative 2

[0052] According to the method in Example 1, the diazo component was replaced with 1.73 g of 2-chloro-4-nitroaniline, and the coupling component was replaced with 3.36 g of 3-(N,N-bis-(carboxypropyl))aminopropionylaniline. Red Derivative 2 was prepared as shown in the following formula.

[0053]

[0054] ( 1 1H NMR (500 MHz, Chloroform-d) δ 9.64 (s, 1H), 8.33 (d, J = 2.2 Hz, 1H), 8.19 (dd, J = 7.9, 2.2 Hz, 1H), 7.85 (d, J = 7.9 Hz, 1H), 7.66 (d, J = 7.2 Hz, 1H), 7.39 (d, J = 1.9 Hz, 1H), 6.65 (dd, J = 7.2, 1.9 Hz, 1H), 3.38 (t, J = 6.2 Hz, 4H), 2.54 (q, J = 7.1 Hz, 2H), 2.43 (s, 1H), 2.39 (s, 1H), 1.89 (tt, J = 9.1, 6.2 Hz, 4H), 1.18 (t, J = 7.1 Hz, 3H).

[0055] Among them, 3-(N,N-bis(3-carboxypropyl))aminopropionylaniline can be prepared according to the method used in the literature US2019048196.

[0056] Example 3

[0057] Synthesis of Red Derivative 3

[0058] According to the method in Example 1, the diazo component was replaced with 2.52 g of 3-bromo-4-aminobenzenesulfonic acid, and the coupling component was replaced with 1.74 g of N-ethyl-N-cyanoethylaniline. Red Derivative 3 was prepared as shown in the following formula.

[0059]

[0060] (1 1H NMR (500 MHz, Chloroform-d) δ 8.28 (d, J = 2.2 Hz, 1H), 8.00 (dd, J = 8.8, 2.2 Hz, 1H), 7.94 (d, J = 8.7 Hz, 1H), 7.78 - 7.73 (m, 2H), 6.85 - 6.79 (m, 2H), 3.69 (t, J = 5.2 Hz, 2H), 3.48 (q, J = 7.3 Hz, 2H), 2.71 (t, J = 5.2 Hz, 2H), 1.17 (t, J = 7.3 Hz, 3H).

[0061] Example 4

[0062] Synthesis of Red Derivative 4

[0063] Add 2.65 g of 4-methyl-2,6-dibromoaniline, 30 mL of water and 2.53 g of hydrochloric acid to a 150 mL three-necked flask, and use an ice-water bath to keep the temperature at 0 - 5 °C. Dissolve 0.70 g of NaNO2 in 6 mL of water, cool it, and then dropwise add it to the above solution while controlling the temperature at 0 - 5 °C. After the addition, continue stirring for 30 min. Use a starch potassium iodide test paper to check. If the test paper turns blue, it indicates that the reaction is complete; otherwise, a small amount of sodium nitrite needs to be added and the above test operation is repeated to obtain the corresponding diazo component.

[0064] Add 1.66 g of 3-(N,N-diethyl)aminobenzeneamine and 1.40 g of sodium formaldehyde bisulfite to 30 mL of water, stir and heat up to 70 °C, and keep the temperature for 2 h to prepare the coupling component. Then cool it to 0 - 5 °C, slowly add the diazo component, control the pH at 4 - 6 with sodium acetate, and ensure the temperature is at 0 - 5 °C. Continue stirring for 2 h, and use H acid to detect whether the reaction reaches the end point. After the reaction is completed, adjust the pH to about 7 with 5% sodium hydroxide solution, filter, collect the filtrate and rotary evaporate to remove the solution, and then purify to remove salt to obtain Intermediate 2 as shown in the following formula.

[0065]

[0066] Cyanate Intermediate 2 according to the method in Example 1 to obtain Red Derivative 4 as shown in the following formula.

[0067]

[0068] ( 11H NMR (500 MHz, Chloroform-d) δ 7.68 (s, 2H), 7.59 (d, J = 7.2 Hz, 1H), 6.83 (t, J = 7.7 Hz, 1H), 6.43 (dd, J = 7.2, 1.9 Hz, 1H), 6.26 (d, J = 1.9 Hz, 1H), 4.62 (d, J = 7.7 Hz, 2H), 3.49 (q, J = 7.1 Hz, 4H), 1.16 (t, J = 7.0 Hz, 6H).

[0069] Preparation of Disperse Ink

[0070] Example 5

[0071] By weight percentage, a red disperse dye ink contains: C.I. Disperse Red 343 (dye) 15%, Red Derivative 1 (derivative dispersant) 1.5%, 3,6-dimethyl-4-octyne-3,6-diol (surfactant) 0.4%, Yus FS3000 (surfactant) 0.4%, glycerol (organic solvent) 10%, ethylene glycol monomethyl ether (organic solvent) 12%, 1,2-benzisothiazol-3-one (preservative) 0.08%, and the balance is deionized water.

[0072] The preparation method of the ink is as follows: Mix the dye, derivative dispersant, surfactant, organic solvent and water evenly according to the above ratio, then grind them in a grinder until the particle size is less than 500 nm, add the preservative, continue to mix for 1 h, and filter out the liquid to obtain a high-temperature direct-injection red disperse dye ink. Denote it as RM-1

[0073] Example 6

[0074] By weight percentage, a red disperse dye ink contains: C.I. Disperse Red 167 (dye) 12%, Red Derivative 2 (derivative dispersant) 1.2%, sodium dodecyl sulfate (surfactant) 0.25%, Surfynol 1465 (surfactant) 0.5%, glycerol (organic solvent) 10%, ethylene glycol monomethyl ether (organic solvent) 12%, 1,2-benzisothiazol-3-one (preservative) 0.1%, and the balance is deionized water.

[0075] Prepare the ink according to the method in Example 5, and denote it as RM-2.

[0076] Example 7

[0077] By weight percentage, a red disperse dye ink contains: C.I. Disperse Red 73 (dye) 8%, red derivative 3 (derivative dispersant) 0.8%, 3,6-dimethyl-4-octyne-3,6-diol (surfactant) 0.3%, CT131 (surfactant) 0.3%, glycerol (organic solvent) 15%, diethylene glycol (organic solvent) 15%, 1,2-benzisothiazol-3-one (preservative) 0.1%, and the balance is deionized water.

[0078] Prepare the ink according to the method in Example 5, denoted as RM-3.

[0079] Example 8

[0080] By weight percentage, a red disperse dye ink contains: C.I. Disperse Red 343 (dye) 10%, red derivative 4 (derivative dispersant) 1.5%, 3,6-dimethyl-4-octyne-3,6-diol (surfactant) 0.3%, Disperbyk 2012 (surfactant) 0.3%, glycerol (organic solvent) 10%, ethylene glycol (organic solvent) 8%, propylene glycol monomethyl ether 8%, 1,2-benzisothiazol-3-one (preservative) 0.1%, and the balance is deionized water.

[0081] Prepare the ink according to the method in Example 5, denoted as RM-4.

[0082] Comparative Example 1

[0083] According to the formulation in Example 5, replace derivative dispersant 1 with an equal amount of RP-Y1 in Patent CN113914116, and keep the others unchanged to prepare a red ink, denoted as RMD-1.

[0084] Comparative Example 2

[0085] According to the formulation in Example 6, replace derivative dispersant 1 with an equal amount of commercially available dispersant NNO, and keep the others unchanged to prepare a red ink, denoted as RMD-2.

[0086] Comparative Example 3

[0087] According to the formulation in Example 7, replace derivative dispersant 1 with an equal amount of commercially available dispersant MF, and keep the others unchanged to prepare a red ink, denoted as RMD-3.

[0088] Comparative Example 4

[0089] According to the formulation in Example 8, replace derivative dispersant 1 with an equal amount of commercially available dispersant 85A, and keep the others unchanged to prepare a red ink, denoted as RMD-4.

[0090] Ink testing and evaluation

[0091] The performance of the red disperse inks of Examples 5-8 and Comparative Examples 1-4 of the present invention was tested as follows:

[0092] 1. Particle size. At room temperature, after diluting the ink, the particle size in the system was measured using a nano particle size distribution analyzer (Brookhaven, NanoBrook Omni).

[0093] 2. Viscosity. At room temperature, the viscosity of the ink was measured using a viscosity tester (AMETEK BROOKFIELD, DV2TLVTJ0).

[0094] 3. pH value. At room temperature, the pH value of the ink was measured using a pH meter (Leici PHS-25).

[0095] 4. Redispersibility. Take 20 g of the ink, and use a UV-Vis spectrophotometer to measure the maximum absorption value at the maximum absorption wavelength (λmax) of the ink, denoted as Abs1; place 20 g of the ink in a 100 ml glass beaker, open it and place it in an oven at 40 °C for 48 h, weigh and record the weight of the dried material, then add pure water to make its weight become 20 g again, stir with a magnetic stirrer for 30 min, filter with a 10 μm syringe filter, and then measure the maximum absorption value of the redispersed solution of the ink at the maximum absorption wavelength (λmax) again, denoted as Abs2. The redispersion rate of the ink = Abs2 / Abs1 * 100%.

[0096] 5. Filterability (flowability). Take 100 g of the ink and record the time it takes to pass through a 1 μm nylon membrane.

[0097] The test results are shown in Table 1 below.

[0098] Table 1

[0099] Item Particle Size (nm) Viscosity (mPa·s) pH Value Redispersion Rate (%) Filtration (s) RM-1 113 2.05 7.56 99.1 8.98 RM-2 123 2.10 7.44 98.6 9.55 RM-3 120 2.09 7.63 98.9 9.10 RM-4 125 2.06 7.45 98.2 9.15 RMD-1 131 2.12 7.59 97.5 10.59 RMD-2 133 2.20 7.68 90.9 13.80 RMD-3 140 2.18 7.33 89.3 12.46 RMD-4 136 2.25 7.55 85.3 12.14

[0100] The above ink was placed in a sealed container and placed in an oven at 60 °C for 14 days, and the above data was measured again. The results are shown in Table 2 below.

[0101] Table 2

[0102] Item Particle Size (nm) Viscosity (mPa·s) pH Value Redispersion Rate (%) Filtration (s) RM-1 118 2.06 7.57 98.8 9.81 RM-2 130 2.09 7.45 98.3 10.91 RM-3 124 2.09 7.66 98.6 10.12 RM-4 130 2.08 7.41 97.8 9.88 RMD-1 140 2.21 7.62 96.1 13.67 RMD-2 151 2.39 7.65 88.7 18.99 RMD-3 166 2.40 7.35 88.1 19.51 RMD-4 158 2.49 7.56 84.5 18.14

[0103] Color difference comparison. After dyeing the cloth with the ink, compare it with its respective standard sample, measure the L*a*b value, and calculate ΔE. The test results are shown in Table 3.

[0104] Table 3

[0105] L a b ΔE Standard Sample (343) 38.667 60.305 9.632 -- RM-1 38.351 59.898 10.105 0.699 RMD-1 37.925 59.38 10.769 1.642 Standard Sample (167) 35.136 52.893 12.084 -- RM-2 34.981 52.288 12.338 0.674 RMD-2 34.392 51.290 12.861 1.930 Standard Sample (73) 36.841 54.358 12.617 -- RM-3 36.589 54.015 12.882 0.501 RMD-3 36.236 56.837 12.921 2.570 Standard Sample (343) 38.667 60.305 9.632 -- RM-4 37.814 60.091 9.255 0.957 RMD-4 37.124 59.510 10.251 1.843

[0106] Comparing Table 1 and Table 2, the data of the inks (RM-1-4) in Examples 5-8 changed little before and after heat storage, while the data of Comparative Examples 1-4 (RMD-1-4) changed significantly, indicating that the properties of the inks of the present invention are superior to those of the comparative examples. The particle size of the inks in Examples 5-8 changed very little before and after heat storage, indicating that the inks have good stability and excellent storage stability. By comparing the filterability (fluidity), the inks in Examples 5-8 only took about 10 s before and after heat storage to pass through a nylon membrane with a pore size of 1 μm, while the time required for the inks in Comparative Examples 1-4 increased, indicating that the inks of the present invention have a good dispersion state and high stability. By comparing the redispersion rate, it can be seen that the inks of the present invention have better redispersibility.

[0107] As can be seen from Table 3, for the cloth dyed with the inks in Examples 5-8, the ΔE value was less than 1 compared with the standard sample, that is, the color difference was small, while for the cloth dyed with the inks in Comparative Examples 1-4, the ΔE value was greater than 1 compared with the standard sample, that is, the color difference was large.

[0108] In summary, the inks of the present invention have good dispersibility, high stability, excellent filterability (fluidity), and a small color difference from the dye itself. The reason why the inks of the present invention have good dispersibility and high stability is that the structure of the red derivative dispersant in Examples 5-8 is similar to the structure of the dye itself, and can interact with the dye molecules to prevent the dye molecules from aggregating. At the same time, the sulfonic acid group or carboxylic acid group carried on the derivative can make it better soluble in water, that is, increase the water solubility of the dye.

Claims

1. Application of a red dye derivative, characterized in that: Use of the red dye derivative as a dispersant in a high-temperature direct-injection red disperse dye ink; The red dye derivative is as shown in Formula I, Formula 1 In the formula, R1 and R2 are the same or different and are selected from hydrogen, C1-C4 alkyl, hydroxyethyl, cyanoethyl, methylsulfonyl, formyl, or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxylic acid group or sulfonic acid group, and n is an integer from 1 to 3; R3 is hydrogen, C1-C4 alkyl, hydroxy, amino, halogen, formamido, acetamido, propionamido, methanesulfonamido or the group -NH(CH2) m -Y, where Y is a carboxyl group or a sulfonic acid group, and m is an integer from 1 to 3; R4 and R5 are the same or different and are selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, cyano, carboxyl or sulfonic acid group; R6 is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, nitro, halogen, cyano, methyl formate group, carboxyl group, sulfonic acid group or phosphoric acid group; And at least one of R1-R6 contains a carboxyl group or a sulfonic acid group.

2. Use of the red dye derivative according to claim 1, characterized in that: In the formula of the red dye derivative, R1 is selected from hydrogen, C1-C4 alkyl, cyanoethyl or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxyl or sulfonic acid group, and n is an integer of 1-3; R2 is selected from hydrogen, C1-C4 alkyl, cyanoethyl, and the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, carboxylic acid group, or sulfonic acid group, and n is an integer from 1 to 3; R3 is selected from hydrogen, chlorine, acetamido, propionamido, methanesulfonamido or the group -NH(CH2) m -Y, where Y is a carboxylic acid group or a sulfonic acid group, and m is an integer from 1 to 3; R4 and R5 can be the same or different and are selected from hydrogen, chlorine, bromine, cyano, carboxyl or sulfonic acid group; R6 is selected from methyl, nitro, carboxyl and sulfonic acid group; And at least one of R1-R6 contains a carboxyl group or a sulfonic acid group.

3. Use of the red dye derivative according to claim 2, characterized in that: In the formula of the red dye derivative, R1 and R2 are the same or different and are selected from alkyl groups having 1 to 4 carbon atoms, cyanoethyl groups or the group -(CH2) n -X, where X is -COOCH3, -OCOCH3, a carboxylic acid group or a sulfonic acid group, and n is an integer from 1 to 3; R3 is selected from hydrogen, chlorine, propionamido, methanesulfonamido or the group -NH(CH2) m -Y, where Y is a carboxylic acid group or a sulfonic acid group, and m is an integer from 1 to 3; R4 and R5 can be the same or different and are selected from hydrogen, chlorine, bromine or cyano; R6 is selected from methyl, nitro, carboxyl and sulfonic acid group; And at least one of R1-R6 contains a carboxyl group or a sulfonic acid group.

4. A disperse dye ink, characterized in that: The disperse dye ink, by weight, comprises 2%-20% of red dye, 0.05%-2% of the red dye derivative according to claim 1, 0.01%-1% of surfactant, 0.01%-1% of preservative, 15%-40% of water-soluble organic solvent and the balance of deionized water.

5. The disperse dye ink according to claim 4, characterized in that: The red dye is a disperse red dye containing an azo structure; The surfactant is one or more of a cationic surfactant, anionic surfactant, amphoteric surfactant and nonionic surfactant.

6. The disperse dye ink according to claim 4, wherein: The preservative is one or several of chlorocresol, 1,2-benzisothiazol-3-one, 2-methyl-4-isothiazolin-3-one, s-triazine, methylene bisthiocyanate; The water-soluble organic solvent is alcohol and / or alcohol ether.

7. The disperse dye ink according to claim 5, characterized in that: The red dye is one or several of C.I. Disperse Red 7, C.I. Disperse Red 12, C.I. Disperse Red 21, C.I. Disperse Red 43, C.I. Disperse Red 56, C.I. Disperse Red 65, C.I. Disperse Red 72, C.I. Disperse Red 73, C.I. Disperse Red 82, C.I. Disperse Red 90, C.I. Disperse Red 97, C.I. Disperse Red 109, C.I. Disperse Red 113, C.I. Disperse Red 118, C.I. Disperse Red 129, C.I. Disperse Red 134, C.I. Disperse Red 167, C.I. Disperse Red 167:1, C.I. Disperse Red 173, C.I. Disperse Red 179, C.I. Disperse Red 188, C.I. Disperse Red 193, C.I. Disperse Red 197, C.I. Disperse Red 210, C.I. Disperse Red 227, C.I. Disperse Red 278, C.I. Disperse Red 311, C.I. Disperse Red 323 and C.I. Disperse Red 343.

8. The disperse dye ink according to claim 5 or 6, characterized in that: The surfactant is an anionic surfactant and / or a nonionic surfactant; The preservative is 1,2-benzisothiazol-3-one and / or 2-methyl-4-isothiazolin-3-one; The water-soluble organic solvent is one or more of ethanol, ethylene glycol, isopropanol, 1,2-propanediol, 1,3-propanediol, glycerol, ethylene glycol monomethyl ether, diethylene glycol, diethylene glycol monomethyl ether, and propylene glycol monomethyl ether.

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