Preparation method and application of special multiplying agent for pigment yellow 138

Abstract

The invention discloses a preparation method and application of a special multiplying agent for pigment yellow 138, and belongs to the technical field of pigment multiplying agents. The multiplying agent prepared by the invention can effectively solve the problem that primary particles of pigment yellow 138 are easy to aggregate, and the primary particles are converted into a finer and more uniform dispersed state, so that the viscosity of a dispersion is reduced, the gelation phenomenon is prevented, and the stability is kept. During long-time storage and use, normal use of the pigment is ensured, segregation or sedimentation is reduced, a coated object is uniformly colored, and tinting strength and an expected effect are ensured. Meanwhile, the pigment crystal state change is inhibited, the defects of tinting strength reduction and the like caused by the crystal state change are avoided, and the excellent properties of the pigment, including high brightness, high saturation hue, chemical stability and light resistance, are maintained. Meanwhile, the flowability of the dispersion is improved, the production efficiency and the application convenience are improved, the performance of the pigment yellow 138 in various aspects is improved, and various requirements of practical application are met.

Description

Technical Field

[0001] The invention belongs to the technical field of pigment multiplying agents, and in particular relates to a preparation method and application of a special multiplying agent for Pigment Yellow 138. Background Art

[0002] Pigment Yellow 138 is an organic pigment widely used in plastics, inks, coatings and other fields. It occupies an important position in many industrial fields due to its excellent color properties, such as high brightness, high saturation yellow hue, as well as good chemical stability and light resistance. For this pigment with high tinting power, their microstructure contains extremely fine primary particles. These primary particles tend to aggregate with each other to form aggregates of primary particles in their actual existence. This aggregation state is a significant obstacle to the full performance of the pigment. In order for the pigment to truly show the excellent properties it should have, it is necessary to implement a dispersion operation on them. The key goal of this process is to transform the pigment from its original aggregation state to a more delicate and uniform dispersion state, so that the various characteristics of the pigment can be effectively released.

[0003] In practice, it is found that as the pigment particles develop in a finer direction, the difficulty of dispersion is increasing. When the pigment particles become finer, the interaction between them and the interaction with the surrounding medium become more complicated, making it difficult to achieve uniform dispersion. Dispersions with unsatisfactory dispersion state will expose a series of problems in many practical application scenarios. First, in terms of physical properties, such dispersions will show the characteristics of high viscosity. High viscosity makes the dispersion face many difficulties during operation, requiring more complex processes to ensure uniform dispersion of pigments, increasing the complexity and cost of operation; during transportation, high-viscosity dispersions have poor fluidity, which puts higher requirements on transportation equipment, and may also lead to reduced transportation efficiency and increased unstable factors during transportation. Secondly, this kind of dispersion with poor dispersion state also has stability problems. The dispersion will gel, and the particles inside the dispersion will combine with each other to form a gel-like structure, which makes the dispersion lose its original fluidity and operability, and thus cannot be used normally. Furthermore, when this dispersion with poor dispersion effect is mixed with other different types of pigments, due to factors such as interactions between pigments and uneven dispersion, the aggregation or sedimentation of pigments often occurs. Segregation will cause local color differences on the surface of the coated object, resulting in uneven coloring; sedimentation will cause uneven distribution of the pigment in the system, which will lead to a significant reduction in the overall coloring power and failure to achieve the expected coloring effect. In addition, when some organic pigments are in a dispersion medium, the crystal state of the pigment will change. In unstable pigment particles, the size or shape will change, and the crystal state will transform into a more stable state. This crystal state transformation often has a negative impact on the performance of the pigment, usually resulting in defects such as a significant reduction in coloring power, a change in color tone, or the generation of coarse particles.

[0004] In response to these problems, after long-term research and practice, it was found that the use of various derivatives with pigment structures or structures similar to them is an effective solution. In past studies, many different types of structures have been disclosed. One type is to obtain pigment derivatives by introducing specific functional groups into the pigment structure, such as acidic groups, basic groups, or special functional groups such as phthalimide methyl. The introduction of these functional groups can change the surface properties and interaction modes of the pigment molecules, thereby having a positive effect on the dispersion performance and stability of the pigment. These specially designed structures have been widely used in the fields of dispersants, particle growth inhibitors, or crystal conversion inhibitors in long-term application practice, and have achieved good results to a certain extent, providing important ideas and methods for solving pigment-related technical problems. In view of this, it is necessary for the present invention to propose a multiplier specifically for Pigment Yellow 138, and apply it to the Pigment Yellow 138 coloring composition of the filter. Summary of the invention

[0005] In view of the above situation, in order to overcome the defects of the prior art, the present invention designs a specific synthesis route and process steps to prepare a special multiplying agent for Pigment Yellow 138 with unique structure and performance, thereby significantly improving the dispersion performance of Pigment Yellow 138, enhancing its stability in various application scenarios, and reducing the adverse effects caused by problems such as pigment aggregation and crystal transition.

[0006] In order to achieve the above object, the following technical scheme is adopted: The present invention provides a method for preparing a special multiplying agent for Pigment Yellow 138, characterized in that it comprises the following steps:

[0007] S1. Add N-methyl-4-bromobenzamide, 3-methyl-3-carboxyl-1-oxetane, potassium carbonate and cuprous iodide to DMF, stir at room temperature until clear, then add acetylcyclohexanone, heat to 105°C and react for 12 hours. After the reaction, add deionized water to the reaction solution, extract with ethyl acetate, collect the aqueous phase, add 10 mol / L hydrochloric acid to the aqueous phase until the pH is 4.0, filter out the precipitated solid, wash with 5°C cold deionized water, and dry to obtain intermediate 1;

[0008] S2, adding the intermediate 1, 1-hydroxybenzotriazole and 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride to anhydrous ethanol, stirring for 4 hours, removing the ethanol under reduced pressure, adding deionized water and continuing to stir for 20 minutes, filtering, washing with deionized water, dissolving the filter cake with dichloromethane, adding anhydrous sodium sulfate to dry, and removing dichloromethane under reduced pressure to obtain intermediate 2;

[0009] S3, dissolving 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine and phenyl chlorothioformate in dichloromethane, stirring at room temperature for 2 hours, filtering after the reaction, collecting the filtrate, removing dichloromethane under pressure to obtain a yellow solid, dissolving the yellow solid with toluene, heating to reflux, maintaining the reaction for 12 hours, then filtering, collecting the filtrate, removing toluene under reduced pressure, and obtaining intermediate three through column chromatography;

[0010] S4, adding the intermediate 2 and intermediate 3 to DMSO, then adding isopropyl acetate, stirring at room temperature until clear, then heating to 90°C for reaction for 10 hours, then cooling to room temperature, adding distilled water for extraction, combining the organic phases, removing the solvent under reduced pressure, recrystallizing with a mixed solution of ethyl acetate and isopropanol in a volume ratio of 2:1, and drying to obtain intermediate 4;

[0011] S5, adding 8-aminoquinaldine and tetrachlorophthalic anhydride to benzoic acid, heating to reflux reaction for 10 hours, then returning to room temperature, adding methanol, filtering, washing the filter cake with deionized water until the filtrate is neutral, and drying to obtain intermediate 5;

[0012] S6. Add intermediate 5 to acetone, then add intermediate 3 to acetone while controlling the temperature at 5°C, and then dropwise add 10% by mass aqueous sodium carbonate solution while continuing to control the temperature at 5°C, filter the obtained product, wash it, and obtain the multiplying agent.

[0013] Furthermore, the multiplying agent has the following structure:

[0014]

[0015] Furthermore, in step S1, the feed ratio of N-methyl-4-bromobenzamide, 3-methyl-3-carboxyl-1-oxetane, potassium carbonate, cuprous iodide, DMF, and acetylcyclohexanone is 10 mmol: 18-20 mmol: 18-20 mmol: 10-13 mmol: 20-30 mL: 2-3 mmol.

[0016] Furthermore, in the step S1, the feed ratio of N-methyl-4-bromobenzamide, 3-methyl-3-carboxy-1-oxetane, potassium carbonate, cuprous iodide, DMF, and acetylcyclohexanone is preferably 10 mmol: 20 mmol: 20 mmol: 13 mmol: 25 mL: 2.5 mmol.

[0017] Furthermore, in the step S2, the feed ratio of the intermediate 1, 1-hydroxybenzotriazole, 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, anhydrous ethanol and deionized water is 5 mmol: 5-7 mmol: 12-15 mmol: 10-15 mL: 40-50 mL.

[0018] Furthermore, in the step S2, the feed ratio of the intermediate 1, 1-hydroxybenzotriazole, 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, anhydrous ethanol and deionized water is preferably 5 mmol: 6 mmol: 12.5 mmol: 12 mL: 45 mL.

[0019] Furthermore, in step S3, the feed ratio of 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine, phenyl chlorothioformate and dichloromethane is 3 mmol: 7-8 mmol: 20-30 mL.

[0020] Furthermore, in the step S3, the feed ratio of 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine, phenyl chlorothioformate and dichloromethane is preferably 3 mmol:7.5 mmol:25 mL.

[0021] Furthermore, in step S4, the feed ratio of intermediate 2, intermediate 3, DMSO and isopropyl acetate is 5 mmol: 6-8 mmol: 20-30 mL: 1-3 mmol.

[0022] Furthermore, in the step S4, the feed ratio of intermediate 2, intermediate 3, DMSO and isopropyl acetate is preferably 5 mmol: 7.5 mmol: 25 mL: 2 mmol.

[0023] Furthermore, in step S5, the feed ratio of 8-aminoquinaldine, tetrachlorophthalic anhydride, benzoic acid and methanol is 3 mmol: 3-6 mmol: 10-15 mL: 10-20 mL.

[0024] Furthermore, in step S5, the feed ratio of 8-aminoquinaldine, tetrachlorophthalic anhydride, benzoic acid and methanol is preferably 3 mmol:4 mmol:12 mL:15 mL.

[0025] Furthermore, in step S6, the feed ratio of intermediate five, acetone, intermediate three and sodium carbonate aqueous solution is 6mmol:20-30mL:6-8mmol:10-20mL.

[0026] Furthermore, in step S6, the feed ratio of intermediate five, acetone, intermediate three and sodium carbonate aqueous solution is preferably 6 mmol:25 mL:7 mmol:15 mL.

[0027] The present invention provides an application of a special multiplying agent for Pigment Yellow 138, comprising the following steps:

[0028] (1) Salt milling: Add Pigment Yellow 138, sodium chloride and diethylene glycol in a mass ratio of 1:8-10:3-5 to a kneader, and perform salt milling at a speed of 50-80 rpm for 10-15 hours;

[0029] (2) Sand milling: Add the salt-milled Pigment Yellow 138, amine dispersant, multiplying agent and alkali-soluble resin into a sand mill in a mass ratio of 1:0.3-1:0.01-0.05:2-3, and sand mill at a speed of 1000-1500 rpm for 3-5 hours to obtain a Pigment Yellow 138 coloring composition.

[0030] The amine dispersant is a combination of one or more of Lubrizol 20000, Lubrizol 24000, Lubrizol 28000, Lubrizol 32000, Lubrizol 32500, Lubrizol 36000, Lubrizol 39000, BYK168, BYK9150, BYK9151, BYK9152, BYK2001, BYK2100, BYK2200, BYK2205, EFKA4310, EFKA4330, EFKA4030, EFKA4700 and EFKA4701.

[0031] Furthermore, the alkali-soluble resin is a combination of one or more of SPC1001, SPC3001 and SPC2000.

[0032] The beneficial effects of the present invention are as follows: the multiplier prepared by the present invention can solve the problem that the primary particles of Pigment Yellow 138 are easy to aggregate, and the pigment is converted from an aggregated state to a more delicate and uniform dispersed state. It can reduce the viscosity of the pigment dispersion, prevent the dispersion from gelling, maintain the stability of the dispersion, and prevent the dispersion from losing fluidity and operability during long-term storage and use, thereby ensuring the normal use of the pigment, reducing the occurrence of segregation or sedimentation, making the surface of the coated object uniformly colored, avoiding local color differences, ensuring the overall coloring power, and achieving the expected coloring effect. The multiplier has an inhibitory effect on the crystal state change phenomenon that is easy to occur in the dispersion medium. It can maintain the stability of the pigment particles in an environment such as a non-aqueous excipient, prevent the crystal state of the pigment from changing in a direction that is not conducive to performance, thereby avoiding defects such as reduced coloring power, color tone change, or generation of coarse particles caused by crystal state change, and maintaining the excellent properties of Pigment Yellow 138 to the greatest extent, such as high brightness, high saturation yellow hue, and good chemical stability and light resistance. The dispersion is easier to handle during operation, improving the fluidity of the dispersion, and improving production efficiency and convenience of application. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 The present invention is a flow chart of a method for preparing a special multiplying agent for Pigment Yellow 138.

[0034] The accompanying drawings are used to provide further understanding of the present invention and constitute a part of the specification. They are used to explain the present invention together with the embodiments of the present invention and do not constitute a limitation of the present invention. DETAILED DESCRIPTION

[0035] The technical solutions in the embodiments of the present invention will be clearly and completely described below in conjunction with the drawings in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0036] Unless otherwise defined, all professional and scientific terms used herein have the same meanings as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to those described herein may be applied to the present invention. The preferred implementation methods and materials described herein are for demonstration purposes only and are not intended to limit the content of this application.

[0037] The experimental methods in the following examples are conventional methods unless otherwise specified, and the experimental materials used in the following examples are purchased from commercial channels unless otherwise specified.

[0038] Example 1

[0039] Preparation of Intermediate 1 and Intermediate 2

[0040] 10 mmol of N-methyl-4-bromobenzamide, 20 mmol of 3-methyl-3-carboxyl-1-oxetane, 20 mmol of potassium carbonate and 13 mmol of cuprous iodide were added to 25 mL of DMF, stirred at room temperature until clear, then 2.5 mmol of acetylcyclohexanone was added, the temperature was raised to 105°C and the reaction was carried out for 12 hours. After the reaction was completed, deionized water was added to the reaction solution, extracted with ethyl acetate, the aqueous phase was collected, 10 mol / L hydrochloric acid was added to the aqueous phase until the pH was 4.0, the precipitated solid was filtered out, washed with 5°C cold deionized water, and dried to obtain intermediate 1;

[0041] 5 mmol of intermediate 1, 6 mmol of 1-hydroxybenzotriazole and 12.5 mmol of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride were added to 12 mL of anhydrous ethanol, stirred for 4 h, and then the ethanol was removed under reduced pressure. Then 45 mL of deionized water was added and continued to stir for 20 min. The mixture was filtered and washed with deionized water. The filter cake was dissolved with dichloromethane, dried with anhydrous sodium sulfate, and then the dichloromethane was removed under reduced pressure to obtain intermediate 2.

[0042] The preparation formulas of the intermediate 1 and intermediate 2 are as follows:

[0043]

[0044] Example 2

[0045] Preparation of Intermediate 3

[0046] Dissolve 3 mmol of 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine and 7.5 mmol of phenyl chlorothioate in 25 mL of dichloromethane and stir at room temperature for 2 h. After the reaction is completed, filter and collect the filtrate. Remove dichloromethane under pressure to obtain a yellow solid. Dissolve the yellow solid with toluene and heat to reflux. Keep the reaction for 12 h. Then filter and collect the filtrate. Remove toluene under reduced pressure and obtain intermediate three through column chromatography.

[0047] The preparation formula of the intermediate three is as follows:

[0048]

[0049] Example 3

[0050] Preparation of Intermediate 4

[0051] 5 mmol of intermediate 2 and 7.5 mmol of intermediate 3 were added to 25 mL of DMSO, and then 2 mmol of isopropyl acetate was added, stirred at room temperature until clear, and then heated to 90°C for reaction for 10 hours, then cooled to room temperature, extracted with distilled water, combined the organic phases, removed the solvent under reduced pressure, and recrystallized with a mixed solution of ethyl acetate and isopropanol in a volume ratio of 2:1, and dried to obtain intermediate 4.

[0052] The preparation formula of the intermediate four is as follows:

[0053]

[0054] Example 4

[0055] Preparation of Intermediate 5

[0056] Add 3 mmol of 8-aminoquinaldine and 4 mmol of tetrachlorophthalic anhydride to 12 mL of benzoic acid, heat to reflux for 10 h, then return to room temperature, add 15 mL of methanol, filter, wash the filter cake with deionized water until the filtrate is neutral, and dry to obtain intermediate 5.

[0057] The preparation formula of the intermediate 5 is as follows:

[0058]

[0059] Example 5

[0060] Preparation of multiplying agents

[0061] 6 mmol of intermediate 5 was added to 25 mL of acetone, and then 7 mmol of intermediate 3 was added to the acetone at a temperature of 5°C, and then 15 mL of a 10% mass fraction sodium carbonate aqueous solution was added dropwise at a temperature of 5°C. The obtained product was filtered and washed to obtain the multiplying agent.

[0062] The preparation formula of the multiplying agent is as follows:

[0063]

[0064] Example 6

[0065] Application of a special multiplying agent for pigment yellow 138

[0066] The following steps are involved:

[0067] (1) Salt milling: Pigment Yellow 138, sodium chloride and diethylene glycol were added to a kneader in a mass ratio of 1:8:3, and salt milling was performed at a speed of 50 rpm for 10 h;

[0068] (2) Sand milling: The salt-milled Pigment Yellow 138, amine dispersant, multiplying agent and alkali-soluble resin were added into a sand mill in a mass ratio of 1:0.3:0.01:2, and sand milled at 1000 rpm for 3 h to obtain a Pigment Yellow 138 coloring composition.

[0069] The amine dispersant is BYK2001, and the alkali-soluble resin is SPC1001.

[0070] Example 7

[0071] Application of a special multiplying agent for pigment yellow 138

[0072] The following steps are involved:

[0073] (1) Salt milling: Pigment Yellow 138, sodium chloride and diethylene glycol were added to a kneader in a mass ratio of 1:10:5, and salt milling was performed at a speed of 80 rpm for 15 h;

[0074] (2) Sand milling: The salt-milled Pigment Yellow 138, amine dispersant, multiplying agent and alkali-soluble resin are added into a sand mill in a mass ratio of 1:1:0.05:3, and the mixture is sand milled at a speed of 1500 rpm until a suitable particle size is reached, thereby obtaining the coloring composition.

[0075] The amine dispersant is a combination of Lubrizol 20000, Lubrizol 32500 and BYK2001 in a mass ratio of 1:1:2; and the alkali-soluble resin is SPC3001.

[0076] Example 8

[0077] Application of a special multiplying agent for pigment yellow 138

[0078] The following steps are involved:

[0079] (1) Salt milling: Pigment Yellow 138, sodium chloride and diethylene glycol were added to a kneader in a mass ratio of 1:9:4, and salt milling was performed at a speed of 60 rpm for 12 h;

[0080] (2) Sand milling: The salt-milled Pigment Yellow 138, amine dispersant, multiplying agent and alkali-soluble resin were added into a sand mill in a mass ratio of 1:0.5:0.02:2.5, and sand milled at 1200 rpm for 4 h to obtain a Pigment Yellow 138 coloring composition.

[0081] The amine dispersant is a combination of Lubrizol 20000, BYK2200 and EFKA4030 in a mass ratio of 1:1:1, and the alkali-soluble resin is SPC2000.

[0082] Example 9

[0083] Application of a special multiplying agent for pigment yellow 138

[0084] In this embodiment, the alkali-soluble resin is a combination of SPC1001, SPC3001 and SPC2000 in a mass ratio of 2:1:1, and the rest is the same as in Embodiment 8.

[0085] Comparative Example 1

[0086] In this comparative example, no multiplying agent prepared by the present invention is added during the sand grinding process, and the remaining components, contents, and preparation process are the same as those of Example 8.

[0087] Comparative Example 2

[0088] In this comparative example, an equal amount of commercially available Lubrizol 22000 is used to replace the multiplying agent prepared by the present invention during the sand grinding process, and the remaining components, contents and preparation process are the same as those of Example 8.

[0089] Test Example 1

[0090] Particle size characterization of coloring compositions

[0091] The particle sizes of the organic pigments in the coloring compositions prepared in the examples and comparative examples were measured by a laser nanoparticle size analyzer. The test results are shown in Table 1.

[0092] It can be seen from the results in Table 1 that the particle size D50 of the coloring composition in Examples 6-9 is in the range of 63.6-66.5 nm, and the particle size is relatively small and relatively stable, which shows that the special multiplying agent for Pigment Yellow 138 prepared by the present invention is effective in dispersing Pigment Yellow 138, and can effectively disperse the pigment particles to a finer degree so that they are evenly distributed in the composition. The particle size D50 of Comparative Example 1 is 145.5 nm, and that of Comparative Example 2 is 112.5 nm, which are significantly larger than those of the embodiments. Since the primary particles of Pigment Yellow 138 are easy to aggregate, poor dispersion will result in larger particle size. The multiplying agent of the present invention successfully overcomes this problem. In contrast, due to the lack of the multiplying agent of the present invention in the comparative example, the pigment dispersion is poor and the particle size is large. This reflects the advantage of the multiplying agent of the present invention in improving the dispersion state of the pigment, which is in line with the beneficial effect of effectively improving the pigment dispersion performance and converting the pigment from an aggregated state to a more fine and uniform dispersion state.

[0093] Table 1 Particle size characterization results of the coloring composition

[0094] project Particle size D50 / nm Example 6 65.5 Example 7 67.8 Example 8 63.6 Example 9 69.5 Comparative Example 1 145.5 Comparative Example 2 112.5

[0095] Test Example 2

[0096] Characterization of tinting strength and viscosity of tinting compositions

[0097] The tinting strength of the coloring compositions prepared in Examples 6-9 and Comparative Examples 1-2 was tested according to the standard of GB / T 13451.2-1992, and the viscosity of the coloring compositions prepared in Examples 6-9 and Comparative Examples 1-2 was tested at 25° C. according to the standard of GB / T 10247-2008. The results are shown in Table 2.

[0098] From the results in Table 2, it can be seen that the tinting power of Examples 6-9 is between 5.5-5.8%, and the viscosity is between 8.3-8.8cp. A higher tinting power means that at the same usage amount, the colored object can present a brighter and richer color, which meets the needs of pigments in practical applications. The lower viscosity makes the coloring composition easier to operate and process during use, and has better fluidity, reducing the operational difficulties and cost increases caused by high viscosity. The tinting power of Comparative Example 1 is 4.3%, and it is non-flowing; the tinting power of Comparative Example 2 is 5.2%, and the viscosity is 12.5cp. Compared with the examples, the tinting power of the comparative examples is significantly lower and the viscosity is higher, which shows that the multiplying agent of the present invention can significantly improve the tinting power of Pigment Yellow 138 while reducing the viscosity of the dispersion.

[0099] Table 2 Characterization results of tinting strength and viscosity of the coloring composition

[0100] project Tinting strength / % Viscosity / cp Example 6 5.5 8.6 Example 7 5.8 8.5 Example 8 5.6 8.3 Example 9 5.5 8.8 Comparative Example 1 4.3 Non-flowing Comparative Example 2 5.2 12.5

[0101] Test Example 3

[0102] Storage stability characterization of multiplying agents

[0103] The coloring compositions prepared in Examples 6-9 of the present invention and Comparative Examples 1-2 were stored at 50°C for 90 days, and the particle size D50 and viscosity of the coloring compositions before and after aging were measured to calculate the changes in particle size and viscosity, and to characterize the temperature stability of the coloring compositions. The test results are shown in Table 3.

[0104] Table 3 Storage stability characterization results of multiplying agents

[0105] project Particle size D50 change / nm Viscosity change / cp Example 6 +5.5 +0.2 Example 7 +6.3 +0.1 Example 8 +5.8 +0.2 Example 9 +5.1 -0.1 Comparative Example 1 +4.3 Unable to test Comparative Example 2 +5.2 +10.5

[0106] It can be seen from the results in Table 3 that after the coloring compositions prepared in Examples 6-9 were stored at 50°C for 90 days, the changes in particle size D50 and viscosity were relatively small, indicating that the coloring composition has good temperature stability, which means that at different ambient temperatures, especially in some application scenarios where temperature changes may occur, the coloring composition of the present invention can maintain the stability of its performance, and will not have problems such as a significant increase in particle size or a significant increase in viscosity due to temperature changes, thereby ensuring the quality and use effect of the product. The changes in particle size and viscosity of the coloring compositions prepared in Comparative Examples 1 and 2 are relatively large, in sharp contrast to the embodiments. The multiplying agent of the present invention plays an important role in improving the temperature stability of the coloring composition, ensuring that Pigment Yellow 138 can maintain good performance under various environmental conditions.

[0107] Test Example 4

[0108] Contrast characterization of coloring compositions

[0109] The contrast and color difference of the coloring compositions prepared in Examples 6-9 and Comparative Examples 1-2 were tested by a colorimeter. The results are shown in Table 4.

[0110] Table 4 Contrast Characterization Results of Coloring Compositions

[0111] project Contrast Example 6 3840 Example 7 4083 Example 8 4233 Example 9 4310 Comparative Example 1 1940 Comparative Example 2 3080

[0112] From the results in Table 4, it can be seen that the contrast ratios of Examples 6-9 are between 3840 and 4310. High contrast ratio means that when the coloring composition is applied, the surface color of the colored object can be made more uniform and brighter, and the color accuracy and stability are also higher, which greatly reduces the quality problems caused by color differences. In contrast, the contrast ratio of Comparative Example 1 is 1940, and the contrast ratio of Comparative Example 2 is 3080. Compared with the examples, the contrast ratios of the comparative examples are significantly lower. It can be concluded that the multiplying agent in the present invention helps to improve the contrast ratio of the coloring composition, so that Pigment Yellow 138 can better exert its color performance in practical applications.

[0113] Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions and variations may be made to the embodiments without departing from the principles and spirit of the present invention, and that the scope of the present invention is defined by the appended claims and their equivalents.

[0114] The present invention and its implementation methods are described above, which is not restrictive. The drawings are only one of the implementation methods of the present invention, and the actual application is not limited thereto. In short, if ordinary technicians in the field are inspired by it and design methods and embodiments similar to the technical solution without creativity without departing from the purpose of the invention, they should all fall within the protection scope of the present invention.

Claims

1. A method for preparing a special multiplying agent for Pigment Yellow 138, characterized in that: The steps include: S1. Add N-methyl-4-bromobenzamide, 3-methyl-3-carboxyl-1-oxetane, potassium carbonate and cuprous iodide to DMF, stir at room temperature until clear, then add acetylcyclohexanone, heat to 105°C and react for 12 hours. After the reaction, add deionized water to the reaction solution, extract with ethyl acetate, collect the aqueous phase, add 10 mol / L hydrochloric acid to the aqueous phase until the pH is 4.0, filter out the precipitated solid, wash with 5°C cold deionized water, and dry to obtain intermediate 1; S2, adding the intermediate 1, 1-hydroxybenzotriazole and 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride to anhydrous ethanol, stirring for 4 hours, removing the ethanol under reduced pressure, adding deionized water and continuing to stir for 20 minutes, filtering, washing with deionized water, dissolving the filter cake with dichloromethane, adding anhydrous sodium sulfate to dry, and removing dichloromethane under reduced pressure to obtain intermediate 2; S3, dissolving 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine and phenyl chlorothioformate in dichloromethane, stirring at room temperature for 2 hours, filtering after the reaction, collecting the filtrate, removing dichloromethane under pressure to obtain a yellow solid, dissolving the yellow solid with toluene, heating to reflux, maintaining the reaction for 12 hours, then filtering, collecting the filtrate, removing toluene under reduced pressure, and obtaining intermediate three through column chromatography; S4, adding the intermediate 2 and intermediate 3 to DMSO, then adding isopropyl acetate, stirring at room temperature until clear, then heating to 90°C for reaction for 10 hours, then cooling to room temperature, adding distilled water for extraction, combining the organic phases, removing the solvent under reduced pressure, recrystallizing with a mixed solution of ethyl acetate and isopropanol in a volume ratio of 2:1, and drying to obtain intermediate 4; S5, adding 8-aminoquinaldine and tetrachlorophthalic anhydride to benzoic acid, heating to reflux reaction for 10 hours, then returning to room temperature, adding methanol, filtering, washing the filter cake with deionized water until the filtrate is neutral, and drying to obtain intermediate 5; S6. Add intermediate 5 to acetone, then add intermediate 3 to acetone while controlling the temperature at 5°C, and then dropwise add 10% by mass aqueous sodium carbonate solution while continuing to control the temperature at 5°C, filter the obtained product, wash it, and obtain the multiplying agent.

2. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: The multiplying agent has the following structure:

3. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S1, the feeding ratio of N-methyl-4-bromobenzamide, 3-methyl-3-carboxyl-1-oxetane, potassium carbonate, cuprous iodide, DMF and acetylcyclohexanone is 10 mmol: 18-20 mmol: 18-20 mmol: 10-13 mmol: 20-30 mL: 2-3 mmol.

4. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S2, the feed ratio of the intermediate 1, 1-hydroxybenzotriazole, 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, anhydrous ethanol and deionized water is 5 mmol: 5-7 mmol: 12-15 mmol: 10-15 mL: 40-50 mL.

5. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S3, the feed ratio of 2,4-diamino-6-(4-chlorophenyl)-1,3,5-triazine, phenyl chlorothioformate and dichloromethane is 3 mmol: 7-8 mmol: 20-30 mL.

6. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S4, the feed ratio of intermediate 2, intermediate 3, DMSO and isopropyl acetate is 5 mmol: 6-8 mmol: 20-30 mL: 1-3 mmol.

7. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S5, the feed ratio of 8-aminoquinaldine, tetrachlorophthalic anhydride, benzoic acid and methanol is 3 mmol: 3-6 mmol: 10-15 mL: 10-20 mL.

8. The preparation method of the special multiplying agent for Pigment Yellow 138 according to claim 1, characterized in that: In the step S6, the feed ratio of intermediate 5, acetone, intermediate 3 and sodium carbonate aqueous solution is 6 mmol: 20-30 mL: 6-8 mmol: 10-20 mL.

9. An application of the special multiplying agent for Pigment Yellow 138 according to any one of claims 1 to 8, characterized in that: The steps include: (1) Salt milling: Add Pigment Yellow 138, sodium chloride and diethylene glycol in a mass ratio of 1:8-10:3-5 to a kneader, and perform salt milling at a speed of 50-80 rpm for 10-15 hours; (2) Sand milling: Add the salt-milled Pigment Yellow 138, amine dispersant, multiplying agent and alkali-soluble resin into a sand mill in a mass ratio of 1:0.3-1:0.01-0.05:2-3, and sand mill at a speed of 1000-1500 rpm for 3-5 hours to obtain a Pigment Yellow 138 coloring composition.

10. The use of the special multiplying agent for Pigment Yellow 138 according to claim 9, characterized in that: The amine dispersant is a combination of one or more of Lubrizol 20000, Lubrizol 24000, Lubrizol 28000, Lubrizol 32000, Lubrizol 32500, Lubrizol 36000, Lubrizol 39000, BYK168, BYK9150, BYK9151, BYK9152, BYK2001, BYK2100, BYK2200, BYK2205, EFKA4310, EFKA4330, EFKA4030, EFKA4700 and EFKA4701; the alkali-soluble resin is a combination of one or more of SPC1001, SPC3001 and SPC2000.

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