阅读说明：本技术 一种含长碳链的匀染性阳离子荧光染料的制备和应用 (Preparation and application of leveling cationic fluorescent dye containing long carbon chain ) 是由 谢孔良 洪广伙 高爱芹 孙介明 侯爱芹 于 2021-08-06 设计创作，主要内容包括：本发明涉及一种含长碳链的匀染性阳离子荧光染料的制备和应用,所述阳离子荧光染料结构如通式I所示。本发明的阳离子荧光染料用于改性涤纶织物染色,上染率、得色量高,颜色鲜艳,匀染性佳,染色织物对不同纤维的耐洗色牢度及干、湿摩擦色牢度均在4-5级及以上。(The invention relates to preparation and application of a leveling cationic fluorescent dye containing long carbon chains, wherein the cationic fluorescent dye has a structure shown in a general formula I. The cationic fluorescent dye is used for dyeing modified polyester fabrics, has high dye uptake and color yield, bright color and good level-dyeing property, and the color fastness to washing and dry and wet rubbing of the dyed fabrics to different fibers is 4-5 grades and above.)

1. A cationic fluorescent dye shown in the following general formula I,

wherein n is an integer of 8-16.

2. The fluorescent dye according to claim 1, wherein the cationic fluorescent dye is in particular:

3. a method of preparing a cationic fluorescent dye comprising:

(1) mixing a solvent and 4-bromo-1, 8-naphthalic anhydride, heating to 45-50 ℃, dropwise adding N, N-dimethylpropylenediamine, heating to reflux temperature after dropwise adding, stirring, monitoring by TLC in the whole process, cooling to room temperature after reaction, purifying, and drying to obtain 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide;

(2) adding fatty amine into 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and a solvent while stirring, heating to 115-130 ℃, carrying out reflux reaction, cooling to room temperature after the reaction is finished, and purifying to obtain 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide;

(3) mixing 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide with a solvent, heating to 45-50 ℃, adding benzyl chloride, heating to 55-65 ℃, stirring for reaction, cooling the reaction solution to room temperature after the reaction is finished, performing suction filtration, and drying to obtain the cationic fluorescent dye.

4. The method according to claim 3, wherein the solvent in the step (1) is ethanol; the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to the N, N-dimethylpropylenediamine is 1: 1.2-1.5; the adopted developing solvent is selected from petroleum ether: ethyl acetate 2:1 (v/v); the reaction time is 0.5-1.5 h.

5. The preparation method according to claim 3, wherein in the step (1), the purification comprises pouring the reaction solution into water, stirring for 5-10 min after the system becomes turbid, standing for 1-2 h, separating out solids, performing suction filtration, and collecting a filter cake.

6. The method according to claim 3, wherein the aliphatic amine in the step (2) is octylamine, dodecylamine or hexadecylamine.

7. The production method according to claim 3, wherein the solvent in the step (2) is ethylene glycol monomethyl ether; the molar ratio of the 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide to the fatty amine is 1: 5-8; the reaction time is 10-25 h.

8. The method according to claim 3, wherein the purification in the step (2) is: adding water into the obtained product, adjusting the pH value of the system to 6-7 by using hydrochloric acid with the mass fraction of 20%, extracting with dichloromethane for three times, collecting organic matters, washing with water for three times, removing water by using anhydrous sodium sulfate, and removing dichloromethane by rotary evaporation.

9. The method according to claim 3, wherein the solvent in the step (3) is acetone; the molar ratio of the 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide to the benzyl chloride is 1: 3-10, and the stirring reaction time is 5-13 h.

10. The use of the cationic fluorescent dye according to claim 1 in modified polyester dyeing.

Technical Field

The invention belongs to the field of cationic fluorescent dyes and preparation and application thereof, and particularly relates to preparation and application of a leveling cationic fluorescent dye containing long carbon chains.

Background

The polyester fiber structure is free of hydrophilic groups, sweat and air permeability are poor, wearing experience is affected, static electricity is easily generated on the surface, fine dust is adsorbed to cause fiber contamination, fluffing and pilling are easy to occur, and researchers can prepare modified polyester fibers by adding a third monomer and even a fourth monomer during molecular polymerization for overcoming the defects. The modified terylene has soft hand feeling and good anti-pilling performance, but fiber molecules are loose, and the dye molecules diffuse fast in the fiber when the fabric is dyed, so that the initial dyeing rate of the dye is higher, the dyeing rate is higher, and uneven fiber dyeing is easy to cause. At present, with the rapid development of modified terylene, part of cationic dyes with good level-dyeing property suitable for modified terylene dyeing are developed, but the cationic fluorescent dyes with good level-dyeing property suitable for modified terylene dyeing are not reported. In order to further expand the application range of the modified polyester fiber, the finding and development of the cationic fluorescent dye with good level-dyeing property suitable for the modified polyester fabric are problems to be solved urgently in the field of printing and dyeing.

CN112143253A cationic fluorescent dye based on a benzyl naphthalimide structure, and preparation and application thereof, and the technical problem of insufficient leveling property.

Disclosure of Invention

The invention aims to solve the technical problem of providing preparation and application of a leveling property cationic fluorescent dye containing a long carbon chain, overcoming the defect of insufficient leveling property in the prior art, and improving the leveling property of the cationic fluorescent dye in the prior art by introducing a long carbon chain structure into a molecular structure. .

The invention provides a cationic fluorescent dye shown in the following structure,

wherein n is an integer of 8-16.

Further, n is 8, 12, 16.

The cationic fluorescent dye is specifically as follows:

the invention provides a preparation method of a cationic fluorescent dye, which comprises the following steps:

(1) preparation of intermediate 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide: mixing a solvent and 4-bromo-1, 8-naphthalic anhydride, heating to 45-55 ℃, dropwise adding N, N-dimethylpropylenediamine, heating to 75-78 ℃ after dropwise adding, stirring, monitoring by TLC in the whole process, cooling to room temperature after the reaction is finished, purifying, and drying to obtain 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide;

(2) adding fatty amine into 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and a solvent while stirring, heating to 115-130 ℃, carrying out reflux reaction, cooling to room temperature after the reaction is finished, and purifying to obtain 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide;

(3) mixing 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide with a solvent, heating to 45-55 ℃, adding benzyl chloride, heating to 55-65 ℃, stirring for reaction, cooling a reaction solution to room temperature after the reaction is finished, separating out a large amount of solids, performing suction filtration, collecting a filter cake, and drying to obtain the cationic fluorescent dye.

The preferred mode of the above preparation method is as follows:

the solvent in the step (1) is ethanol; the molar ratio of the 4-bromo-1, 8-naphthalic anhydride to the N, N-dimethylpropylenediamine is 1: 1.2-1.5; the adopted developing solvent is selected from petroleum ether: ethyl acetate 2:1 (v/v); the reaction time is 0.5-1.5 h (the reaction time is the reaction time after the temperature is raised to the reflux temperature).

And (2) in the step (1), the purification is to pour the reaction solution into water, stir the system for 5-15 min, stand for 1-2 h, separate out solids, filter and collect filter cakes.

And (3) in the step (2), the aliphatic amine is octylamine, dodecylamine or hexadecylamine.

The solvent in the step (2) is ethylene glycol monomethyl ether; the molar ratio of the 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide to the fatty amine is 1: 5-8; the reaction time is 10-25 h.

The purification in the step (2) is as follows: adding water into the obtained product, adjusting the pH value of the system to 6-7 by using hydrochloric acid with the mass fraction of 20%, extracting with dichloromethane for three times, collecting organic matters, washing with water for three times, removing water by using anhydrous sodium sulfate, and removing dichloromethane by rotary evaporation.

The solvent in the step (3) is acetone; the molar ratio of the 4-alkylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide to the benzyl chloride is 1: 3-10, and the stirring reaction time is 5-13 h.

The cationic fluorescent dye is applied to modified polyester dyeing, so that dyed fabrics are bright in color, show bright yellow fluorescence under an ultraviolet lamp, are excellent in level-dyeing property and have excellent color fastness, particularly washing color fastness and rubbing color fastness which are both 4-5 grades and above.

The modified polyester is obtained by adding a third monomer of 3, 5-dimethyl benzene dicarboxylic acid sodium Sulfonate (SIPM) into polyester fiber, and the density/10 cm is 570 (warp) multiplied by 290 (weft); gram weight 157g m^-2。

The invention relates to a preparation method of a leveling property cationic fluorescent dye containing a long carbon chain, which comprises the following preparation formula:

advantageous effects

(1) The cationic fluorescent dye provided by the invention is novel in structure, is used for dyeing modified polyester fabrics, and expands the application range of the modified polyester fabrics;

(2) the cationic fluorescent dye containing the long carbon chain naphthalimide structure is used for modifying dyeing dye uptake of terylene, and has high dye yield and good level dyeing property;

(3) the cationic fluorescent dye containing the long carbon chain naphthalimide structure provided by the invention is excellent in various color fastness when used for modified polyester dyeing.

(4) The structural dye is used for dyeing modified polyester fabrics, has bright color, shows bright yellow green fluorescence under an ultraviolet lamp, has excellent level-dyeing property and excellent color fastness, particularly washing color fastness and rubbing color fastness which are both 4-5 grades and above.

Drawings

FIG. 1 is a FTIR spectrum of cationic fluorescent dye I obtained in example 1;

FIG. 2 is a fluorescence spectrum of the cationic fluorescent dye I obtained in example 1;

FIG. 3 is a FTIR spectrum of cationic fluorescent dye II obtained in example 2;

FIG. 4 is a fluorescence spectrum of the cationic fluorescent dye II obtained in example 2;

FIG. 5 is a FTIR spectrum of the cationic fluorescent dye III obtained in example 3;

FIG. 6 is a fluorescence spectrum of the cationic fluorescent dye III obtained in example 3;

FIG. 7 is a graph of a modified polyester fabric dyeing process;

FIG. 8 is a photograph of modified polyester fabric dyed with cationic fluorescent dye I under an ultraviolet lamp in example 7;

FIG. 9 is a photograph of modified polyester fabric dyed with cationic fluorescent dye II under an ultraviolet lamp in example 8;

FIG. 10 is a photograph of modified polyester fabric dyed with cationic fluorescent dye III under an ultraviolet lamp in example 9.

Detailed Description

The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.

The drugs and materials used in the examples were: the modified polyester is obtained by adding a third monomer of 3, 5-dimethyl benzene dicarboxylate sodium Sulfonate (SIPM) into polyester fiber, and the density/10 cm:570 (warp) × 290 (weft), grammage: 157g/m²Supplied by Zhejiang Shengfa textile printing and dyeing Co., Ltd; 4-bromo-1, 8-naphthalic anhydride (98%), octylamine (99%), dodecylamine (99%), hexadecylamine (99%), dichloromethane (99%)5%), benzyl chloride (99%) purchased from Shanghai Tantake technologies, Inc.; anhydrous ethanol (99.5%), ethylene glycol monomethyl ether (99%), and N, N-dimethylpropylene diamine (99%) were purchased from national pharmaceutical group chemical agents, Inc.

Example 1

(1) 100mL of ethanol and 10.0g of 4-bromo-1, 8-naphthalic anhydride are sequentially added into a 250mL three-neck flask, the temperature is raised to 50 ℃, 5.45mL of N, N-dimethyl propane diamine is gradually dripped, the temperature is raised to 78 ℃ after the dripping is finished, and the mixture is stirred. The whole process is monitored by TLC, and the developing solvent is petroleum ether: ethyl acetate 2:1 (v/v). After 30min, the reaction is finished, the reaction solution is cooled to room temperature, the reaction solution is poured into water, the system becomes turbid, the reaction solution is stirred for 10min, the reaction solution is kept stand for 1h, a large amount of solid is separated out, the filtration is carried out, a filter cake is collected and dried, and 10.56g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide is obtained.

(2) 6.40g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 21mL of ethylene glycol monomethyl ether were placed in a 100mL three-necked flask, 19.29mL of octylamine was added while stirring, the temperature was raised to 127 ℃ and the reaction was carried out under reflux for 10 hours. After the reaction is finished, cooling to room temperature, adding water into the obtained product, adjusting the pH value of the system to 6-7 by using hydrochloric acid with the mass fraction of 20%, extracting with dichloromethane for three times, collecting organic substances, washing with water for three times, removing water by using anhydrous sodium sulfate, and removing dichloromethane by rotary evaporation to obtain 4-octylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide.

(3) Adding 3.92g of 4-octylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 30mL of acetone into a reactor, heating to 50 ℃, adding 5.73mL of benzyl chloride, heating to 60 ℃, stirring for reaction for 9.5h, cooling reaction liquid to room temperature after the reaction is finished, separating out a large amount of solids, carrying out suction filtration, collecting a filter cake, and drying to obtain the cationic fluorescent dye I, wherein the yield is 56.32%.

(4) The Infrared (FTIR) spectrum and the fluorescence spectrum of the cationic fluorescent dye I obtained in the test (3) were measured, and the results are shown in fig. 1 and fig. 2, respectively.

Example 2

(1) 100mL of ethanol and 10.0g of 4-bromo-1, 8-naphthalic anhydride are sequentially added into a 250mL three-neck flask, the temperature is raised to 50 ℃, 5.45mL of N, N-dimethyl propane diamine is gradually dripped, the temperature is raised to 78 ℃ after the dripping is finished, and the mixture is stirred. The whole process is monitored by TLC, and the developing solvent is petroleum ether: ethyl acetate 2:1 (v/v). After 30min, the reaction is finished, the reaction solution is cooled to room temperature, the reaction solution is poured into water, the system becomes turbid, the reaction solution is stirred for 10min, the reaction solution is kept stand for 1h, a large amount of solid is separated out, the filtration is carried out, a filter cake is collected and dried, and 10.56g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide is obtained.

(2) 5.52g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 30mL of ethylene glycol monomethyl ether were charged into a 100mL three-necked flask, 29.70mL of dodecylamine was added while stirring, the temperature was raised to 127 ℃ and the reaction was carried out under reflux for 18 hours. After the reaction is finished, cooling to room temperature, adding water into the obtained product, adjusting the pH value of the system to 6-7 by using hydrochloric acid with the mass fraction of 20%, extracting with dichloromethane for three times, collecting organic substances, washing with water for three times, removing water by using anhydrous sodium sulfate, and removing dichloromethane by rotary evaporation to obtain 4-dodecadiamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide.

(3) Adding 4.66g of 4-dodecaamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 30mL of acetone into a reactor, heating to 50 ℃, adding 5.40mL of benzyl chloride, heating to 60 ℃, stirring for reaction for 7h, cooling reaction liquid to room temperature after the reaction is finished, separating out a large amount of solids, carrying out suction filtration, collecting a filter cake, and drying to obtain the cationic fluorescent dye II with the yield of 60.75%.

(4) The Infrared (FTIR) spectrum and the fluorescence spectrum of the cationic fluorescent dye II obtained in the test (3) were shown in fig. 3 and 4, respectively.

Example 3

(1) 100mL of ethanol and 10.0g of 4-bromo-1, 8-naphthalic anhydride are sequentially added into a 250mL three-neck flask, the temperature is raised to 50 ℃, 5.45mL of N, N-dimethyl propane diamine is gradually dripped, the temperature is raised to 78 ℃ after the dripping is finished, and the mixture is stirred. The whole process is monitored by TLC, and the developing solvent is petroleum ether: ethyl acetate 2:1 (v/v). After 30min, the reaction is finished, the reaction solution is cooled to room temperature, the reaction solution is poured into water, the system becomes turbid, the reaction solution is stirred for 10min, the reaction solution is kept stand for 1h, a large amount of solid is separated out, the filtration is carried out, a filter cake is collected and dried, and 10.56g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide is obtained.

(2) 3.00g of 4-bromo-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 36mL of ethylene glycol monomethyl ether were added to a 100mL three-necked flask, 17.00g of hexadecylamine was added while stirring, the temperature was raised to 127 ℃, and the mixture was refluxed for 22 hours. And after the reaction is finished, cooling to room temperature, adding water into the obtained product, adjusting the pH value of the system to 6-7 by using 20% hydrochloric acid by mass, separating out a large amount of solid, performing suction filtration, and drying to obtain the 4-hexadecylamino-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide.

(3) Adding 3.00g of 4-hexadecylamine-N- (N, N-dimethyl) propylamino-1, 8-naphthalimide and 30mL of acetone into a reactor, heating to 50 ℃, adding 7.50mL of benzyl chloride, heating to 60 ℃, stirring for reacting for 13h, cooling the reaction solution to room temperature after the reaction is finished, separating out a large amount of solid, performing suction filtration, collecting a filter cake, and drying to obtain the cationic fluorescent dye III, wherein the yield is 64.83%.

(4) The Infrared (FTIR) spectrum and the fluorescence spectrum of the cationic fluorescent dye III obtained in the test (3) were shown in fig. 5 and 6, respectively.

Example 4

The cationic fluorescent dye I obtained in example 1 was used to dye a modified polyester fabric according to the dyeing process graph shown in fig. 7. Specifically, dyeing the cloth sample at 30 ℃, raising the temperature to 120 ℃ at the speed of 1 ℃/min, carrying out heat preservation dyeing at 120 ℃ for 40min, and then naturally cooling to 60 ℃. And (3) soaping the dyed fabric for 15min at 85 ℃, washing with water, and drying, wherein the soaping agent is 1.0g/L washing powder, and the soaping bath ratio is 1: 20. The dosage of the ionic fluorescent dye I during dyeing is 2.0 (o.w.f%), and the bath ratio is 1: 20. And testing the dye uptake, the color yield and the color difference of the dye after dyeing.

The dye uptake test method comprises the following steps: and (3) soaping and washing the dyed cloth sample, collecting the dyeing residual liquid and the colored cleaning liquid, reasonably diluting the dyeing residual liquid and the colored cleaning liquid to a certain multiple, testing the absorbance of the dyeing residual liquid and the colored cleaning liquid by an ultraviolet spectrophotometer, and calculating the dyeing uptake rate according to the ratio of the absorbance to the absorbance of the dyeing stock solution. In the experiment, Integ value is selected to represent the color yield of the dyed fabric, a Datacolor D-650 computer color measuring and matching instrument is adopted, and the color measuring light source is D₆₅A light source for emitting light from a light source,at 10 ° viewing angle, 5 measurements per sample were averaged. According to the test, the dyeing uptake of the cationic fluorescent dye I in the example is 98.23%, the Integ value of the color yield of the cloth sample is 12.96, and the color difference value is 0.21. The cationic fluorescent dye I is used for dyeing modified polyester fabrics, and has high dye uptake, high color yield and good level-dyeing property.

The photo of the dyed fabric sample under the ultraviolet lamp is shown in fig. 8, and the photo shows that the cationic fluorescent dye I dyed fabric has bright yellow green fluorescence under the irradiation of the 365nm ultraviolet lamp, and the dyed fabric has bright color and no color spots and flaws, which indicates that the cationic fluorescent dye I dyed modified polyester fabric has good level-dyeing property.

Reference is made to GB/T3920-: xenon arc test Standard the dyed fabric was tested for various colorfastness properties (same as the test standards for other examples), and the test results are shown in Table 1. The results in table 1 show that the dry and wet rubbing color fastness and the washing fastness to acetate, cotton, terylene, chinlon, acrylic fiber and wool fiber of the cationic fluorescent dye I dyed modified terylene fabric reach 4-5 grades and above, which indicates that the cationic fluorescent dye I has excellent color fastness to dyeing of the modified terylene fabric.

TABLE 1 color fastness of modified polyester fabrics dyed with cationic fluorescent dye I

Example 5

The modified polyester fabric was dyed using the cationic fluorescent dye II obtained in example 2 according to the dyeing process graph shown in fig. 7, wherein the amount of the cationic fluorescent dye II was 2.0 (o.w.f%), the bath ratio was 1:20, the dye uptake of the test dye after dyeing was 98.47%, the cloth sample color yield Integ value was 13.80, and the color difference value was 0.29. The result shows that the cationic fluorescent dye II is used for dyeing modified polyester fabrics, and has high dye uptake, high color yield and good level-dyeing property.

The photo of the dyed fabric sample under the ultraviolet lamp is shown in fig. 9, and the photo shows that the cationic fluorescent dye II dyed fabric has bright yellow green fluorescence under the irradiation of the 365nm ultraviolet lamp, and the dyed fabric has bright color and no color spots and flaws, which indicates that the cationic fluorescent dye II dyed modified polyester fabric has good level-dyeing property. The results of the various color fastness tests are shown in table 2. The results in Table 2 show that the dry and wet rubbing color fastness and the washing fastness of the modified polyester fabric dyed by the cationic fluorescent dye II reach 4-5 levels, and the cationic fluorescent dye II has excellent color fastness on the dyeing of the modified polyester fabric.

TABLE 2 color fastness of modified polyester fabrics dyed with cationic fluorescent dye II

Example 6

Using the cationic fluorescent dye III obtained in example 3, dyeing was performed on the modified polyester fabric according to the dyeing process graph shown in fig. 7, wherein the amount of the cationic fluorescent dye III was 2.0 (o.w.f%), the bath ratio was 1:20, the dye uptake of the test dye after dyeing was 98.90%, the cloth sample color yield Integ value was 14.25, and the color difference value was 0.33. The cationic fluorescent dye III is used for dyeing modified polyester fabrics, and has high dye uptake, high color yield and good level-dyeing property.

The photo of the dyed fabric sample under the ultraviolet lamp is shown in fig. 10, and the photo shows that the cationic fluorescent dye III dyed fabric has bright yellow green fluorescence under the irradiation of the 365nm ultraviolet lamp, and the dyed fabric has bright color and no color spots or flaws, which indicates that the cationic fluorescent dye III dyed modified polyester fabric has good level-dyeing property. The results of the various color fastness tests are shown in table 3. The results in Table 3 show that the dry and wet rubbing color fastness and the washing fastness of the modified polyester fabric dyed by the cationic fluorescent dye III are all up to 4-5 grades and above, and the cationic fluorescent dye III has excellent color fastness on the dyeing of the modified polyester fabric.

TABLE 3 color fastness of modified polyester fabrics dyed with cationic fluorescent dye III

Comparative example 1

The results of comparing the dye uptake and the color difference of the dyes using the cationic fluorescent dye (1) and the cationic fluorescent dye (2) of the invention CN112143253A by the same dyeing process as in examples 4 to 6 are shown in table 4.

As can be seen from the comparison of the dye uptake and the color difference value in the table 4, the cationic fluorescent dye of the invention has more stable dye uptake and smaller color difference value when used for dyeing modified terylene, which indicates that the cationic fluorescent dye of the invention has more excellent level-dyeing property than the cationic fluorescent dye of the invention CN 112143253A.

TABLE 4 comparison of the dye uptake and color difference values of the inventive CN112143253A and the inventive cationic fluorescent dye