Preparation method of pigment red 254 coloring composition for color filter

Abstract

The invention discloses a preparation method of a pigment red 254 coloring composition for a color filter, and belongs to the technical field of preparation of pigment coloring compositions. The pigment red 254 is subjected to bromine substitution treatment through bromination reaction, active sites are provided for modification of the acrylate monomer, the pigment is modified by utilizing the acrylate monomer through Heck reaction, pigment molecules are promoted to form solvated chains through modification of the acrylate monomer, and the surface energy of the pigment molecules is effectively reduced; according to the present invention, the affinity of the pigment red 254 in the dispersion medium is significantly improved, the agglomeration phenomenon is reduced, the particle size of the pigment red 254 is effectively reduced, the uniformity and the stability of the coloring composition are ensured, the coloring power of the pigment is improved, and the performance of the pigment in the final product is enhanced. Through the preparation method, the application range of the pigment red 254 is expanded, and the pigment red 254 can be more effectively applied to multiple fields such as color filters and printing ink.

Description

Technical Field

[0001] The invention belongs to the technical field of pigment coloring composition preparation, and in particular relates to a method for preparing a pigment red 254 coloring composition for a color filter. Background Art

[0002] Organic pigments are a class of compounds composed of elements such as carbon and hydrogen. They are evenly dispersed in the medium in the form of tiny particles to provide color for various materials. These pigments can be divided into two categories: natural and synthetic. Natural organic pigments such as acid blue and carmine are extracted from plants, animals or microorganisms. They are bright in color but have poor stability. Synthetic organic pigments are synthesized through chemical reactions, have better stability and color vividness, and are widely used in many industries such as color filters and inks.

[0003] In the production of color filters, the use of organic pigments, especially red coloring compositions, is crucial. These compositions usually contain coloring pigments, pigment dispersants, resins, and organic solvents. However, traditional red coloring compositions have problems such as difficulty in dispersing pigments and poor stability after dispersion during the dispersion process. These problems limit the performance of color filters, especially in terms of contrast and brightness. Therefore, in order to solve these problems, it is necessary to improve the contrast of red filters through modification. Summary of the invention

[0004] In view of the above situation, in order to overcome the defects of the prior art, the present invention adopts the method of acrylate modification to prepare the Pigment Red 254 coloring composition, the affinity of which is significantly improved, the particle size is effectively reduced, the coloring composition has good uniformity and stability, strong coloring, and has light resistance, weather resistance and heat resistance.

[0005] In order to achieve the above object, the following technical scheme is adopted: The present invention provides a method for preparing a pigment red 254 coloring composition for a color filter, comprising:

[0006] S1. Bromination treatment of Pigment Red 254: add the bromide salt to deionized water, stir and dissolve, then add benzyltriethylammonium bromide, dichloromethane and Pigment Red 254, heat to 150-180°C, pressure of 2-3MPa, react for 5-8h, complete the reaction, separate the liquids, filter the organic phase, remove the solvent and impurities by distillation under reduced pressure, and obtain bromine-substituted Pigment Red 254 after drying;

[0007] S2. Modification of bromine-substituted pigment red 254 by acrylate: acid-binding agent and Pd 2 (dba) 3Add toluene, stir for 5-10 minutes, add acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 under vacuum protection, react at 80-90°C for 1.5-3 hours, add to excess deionized water, separate the liquids, distill the organic phase under reduced pressure to remove the solvent, and dry to obtain acrylate-modified Pigment Red 254;

[0008] S3, preparation of organic pigment red 254: after heating isopropanol to reflux, acrylate-modified pigment red 254, azobisisobutyronitrile, hydroquinone and sodium dodecylsulfonate are mixed and slowly added to isopropanol, and after the addition is completed, the reaction is continued for 3-6 hours, and then the heating is stopped, and triethylamine is added after returning to room temperature. After mixing evenly, the mixture is filtered, washed with deionized water for 3 times, and dried to obtain organic pigment red 254;

[0009] S4, salt grinding treatment of organic pigment red 254: adding the organic pigment red 254, sodium chloride and diethylene glycol in a mass ratio of 1:8-12.5:3-5 to a kneader, and salt grinding treatment is performed at a speed of 50-80 rpm for 10-15 hours;

[0010] S5. Sand-milling the organic pigment red 254: adding the salt-milled organic pigment red 254, the amine dispersant and the alkali-soluble resin into a sand mill, and sand-milling at a rotation speed of 1000-1500 rpm until a suitable particle size is obtained, and then stopping the sand-milling to obtain the coloring composition.

[0011] Furthermore, the bromide salt is a combination of one or more of lithium bromide, potassium bromide, calcium bromide, sodium bromide, magnesium bromide, ferrous bromide, zinc bromide and copper bromide.

[0012] Furthermore, the bromide salt is preferably a combination of potassium bromide and sodium bromide.

[0013] Furthermore, the bromide salt is preferably a combination of potassium bromide and sodium bromide in a mass ratio of 1:1.

[0014] Furthermore, in step S1, the mass ratio of the bromide salt, deionized water, benzyltriethylammonium bromide and Pigment Red 254 is 10-15:30-50:1-2.5:12.5-20.

[0015] Furthermore, in step S1, the mass ratio of the bromide salt, deionized water, benzyltriethylammonium bromide and Pigment Red 254 is preferably 12:40:1.5:15.

[0016] Furthermore, the acid binding agent is one of sodium carbonate, potassium carbonate, cesium carbonate, sodium tert-butoxide and potassium tert-butoxide.

[0017] Furthermore, the acid binding agent is preferably sodium tert-butoxide.

[0018] Furthermore, the acrylic acid ester monomer is one of methyl acrylate, ethyl acrylate, 2-methyl methacrylate and 2-ethyl methacrylate, and the acrylic acid ester monomer is preferably 2-methyl methacrylate.

[0019] Furthermore, in step S2, the acid binding agent, Pd 2 (dba) 3 The feed mass ratio of toluene, acrylate monomer, triethanolamine and bromine-substituted pigment red 254 is 5-10: 0.1-0.2: 50-80: 3-5: 1-2: 5-10.

[0020] Furthermore, in step S2, the acid binding agent, Pd 2 (dba) 3 The preferred feed mass ratio of , toluene, acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 is 8:0.15:60:4:1.5:8.

[0021] Furthermore, in step S3, the mass ratio of isopropanol, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is 50-100: 5-8: 0.01-0.1: 0.05-0.1: 0.5-2: 10-30.

[0022] Furthermore, in step S3, the feed mass ratio of isopropanol, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is preferably 60:7:0.05:0.08:1.5:15.

[0023] Further, 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.

[0024] Furthermore, the amine dispersant is preferably a combination of Lubrizol 20000, Lubrizol 32500 and BYK2001.

[0025] Furthermore, the amine dispersant is preferably a combination of Lubrizol 20000, Lubrizol 32500 and BYK2001 in a mass ratio of 3:1:2.

[0026] Furthermore, the alkali-soluble resin is a combination of one or more of SPC1001, SPC3001 and SPC2000.

[0027] Furthermore, the alkali-soluble resin is preferably SPC2000.

[0028] Furthermore, in the step S5, the mass ratio of the organic pigment red 254, the amine dispersant and the alkali-soluble resin after salt grinding is 1:0.3-1:2.5-3.

[0029] The mass ratio of the organic pigment red 254, the amine dispersant and the alkali-soluble resin after salt grinding in step S5 is preferably 1:0.5:2.8.

[0030] The nitrogen atom of amine dispersants has an unshared electron pair and can accept protons, so it has alkalinity. The alkalinity of amine dispersants enables them to react with a variety of substances, including forming salts with acids, and participating in various organic synthesis reactions. This chemical activity of amine dispersants enables them to enhance and improve the dispersibility of solid or liquid materials.

[0031] Alkali-soluble resins can be dissolved by alkali at high pH values ​​to form a developed pattern. At the same time, alkali-soluble resins can assist pigment dispersants to help pigments disperse evenly in the medium, improve the tinting power and stability of the coloring composition, and improve the properties of the coloring composition, such as particle size, gloss and dispersion stability.

[0032] In the above preparation method, salt grinding and sand grinding are two key steps, which have a significant impact on the final properties of the pigment.

[0033] The main function of salt grinding is to reduce the dispersibility and original particle size of the pigment by physical methods. During the salt grinding process, the pigment is mixed and kneaded in a kneader together with a large amount of inert medium (such as sodium chloride). This treatment can break up the pigment aggregates and reduce the interaction force between the pigment particles, thereby reducing the original particle size of the pigment particles and narrowing the particle distribution through the extrusion and friction of salt.

[0034] Sanding is a more sophisticated physical processing process, which aims to make the processed pigments stably dispersed in the medium. Using equipment such as sand mills, the pigments are impacted and sheared by high-speed rotating sanding media, and the pigment particles are refined to obtain a more uniform particle size distribution. This step is crucial to improving the coloring power, transparency and gloss of the pigment. During the sanding process, additives such as dispersants and alkali-soluble resins are added to enhance the stability and dispersibility of the pigment. The anchoring effect of the dispersant on the pigment is strengthened by forming hydrogen bonds between the introduced ester group and the amine group of the dispersant. At the same time, due to the similar structure between the ester group and the lipid solvent, the affinity between the solvent can be better strengthened, thereby maintaining the stability of the dispersed state.

[0035] The beneficial effects of the present invention are as follows: the present invention firstly performs bromine substitution treatment on Pigment Red 254 through a bromination reaction, and this step provides an active site for the subsequent modification of an acrylate monomer. Then, the pigment is modified by using an acrylate monomer through a Heck reaction. The modification of the acrylate monomer causes the pigment molecules to form a solvation chain, thereby significantly improving the affinity of Pigment Red 254 in the dispersion medium, reducing the occurrence of agglomeration, and thereby effectively reducing the particle size of Pigment Red 254, ensuring the uniformity and stability of the coloring composition. Through this fine dispersion state, not only the tinting power of the coloring composition is improved, but also the contrast and brightness of the coloring composition are improved, and its performance in the final product, such as light resistance, weather resistance and heat resistance, is enhanced. Through this preparation method, the application scope of Pigment Red 254 is expanded, and it can be more effectively applied to multiple fields such as color filters and inks. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 The present invention is a flow chart of a method for preparing a pigment red 254 coloring composition for a color filter.

[0037] 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

[0038] 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.

[0039] 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.

[0040] 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.

[0041] The purity of the brominated salt is ≥99.0%; the benzyl triethyl ammonium bromide is analytically pure, with a purity of ≥98.0%; the dichloromethane is ACS pure, with a purity of ≥99.0%; the purity of the pigment red 254 is ≥98.0%; the acid binding agent is premium pure, with a purity of ≥99.5%; the Pd 2 (dba) 3 The purity of the toluene monomer is ≥99.95%; the purity of the toluene monomer is ≥95.0%; the purity of the acrylate monomer is ≥99.5%; the triethanolamine is gas chromatography grade, with a purity of ≥99.5%; the purity of azobisisobutyronitrile is ≥95.0%; the hydroquinone is analytical grade, with a purity of ≥99.0%; the sodium dodecyl sulfonate is gas chromatography grade, with a purity of ≥98.0%; the isopropanol is spectrally pure, with a purity of ≥99.5%; the purity of the triethylamine is ≥99.9%; the Lubrizol 20000, Lubrizol 24000, Lubrizol 28000, Lubrizol 32000, Lubrizol 3 BYK 2500, Lubrizol 36000 and Lubrizol 39000 were purchased from Lubrizol Corporation of the United States; BYK168, BYK9150, BYK9151, BYK9152, BYK2001, BYK2100, BYK2200 and BYK2205 were purchased from BYK Chemicals of Germany; EFKA4310, EFKA4330, EFKA4030, EFKA4700 and EFKA4701 were purchased from BASF of Germany; SPC1001, SPC3001 and SPC2000 were purchased from Showa Polymer Co., Ltd. of Japan.

[0042] The particle size of the coloring composition was measured using a laser particle size distribution analyzer, model: Malvern zs90.

[0043] The viscosity of the coloring composition was measured using a coloring composition viscosity tester, model NDJ-9T.

[0044] Example 1

[0045] A method for preparing a pigment red 254 coloring composition for color filters

[0046] The preparation method comprises:

[0047] S1. Bromination: Add the bromide salt to deionized water, stir and dissolve, then add benzyltriethylammonium bromide, dichloromethane and Pigment Red 254, heat to 150°C, pressure 2MPa, react for 5h, after the reaction is completed, separate the liquids, filter the organic phase, and then distill under reduced pressure to remove the solvent and impurities, and dry to obtain bromine-substituted Pigment Red 254;

[0048] S2, acrylate modification: acid binding agent and Pd 2 (dba) 3Add toluene, stir for 5 minutes, add acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 under vacuum protection, react at 80°C for 1.5 hours, add to excess deionized water, separate the liquids, distill the organic phase under reduced pressure to remove the solvent, and dry to obtain acrylate-modified Pigment Red 254;

[0049] S3, preparation of organic pigment: after heating isopropanol to reflux, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone and sodium dodecylsulfonate are mixed and slowly added to isopropanol, and the reaction is continued for 3 hours after the addition is completed, and then the heating is stopped, and triethylamine is added after returning to room temperature, and after mixing evenly, the mixture is filtered, washed with deionized water for 3 times, and dried to obtain organic Pigment Red 254;

[0050] S4, salt milling: adding the organic pigment Red 254, sodium chloride and diethylene glycol in a mass ratio of 1:8:3 to a kneader, and performing salt milling treatment at a speed of 50 rpm for 10 hours;

[0051] S5, sand milling: adding the salt-milled organic pigment Red 254, the amine dispersant and the alkali-soluble resin into a sand mill, sand milling at a rotation speed of 1000 rpm until the particles have a suitable particle size, and then stopping the sand milling to obtain the coloring composition.

[0052] The bromide salt is lithium bromide; the mass ratio of bromide salt, deionized water, benzyl triethyl ammonium bromide and pigment red 254 in step S1 is 10:30:1:12.5; the acid binding agent is sodium carbonate; the acrylate monomer is methyl acrylate; the acid binding agent, Pd 2 (dba) 3 , toluene, acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 are fed in a mass ratio of 5:0.1:50:3:1:5; in the step S3, the mass ratio of isopropanol, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is 50:5:0.01:0.05:0.5:10; the amine dispersant is Lubrizol 20000; the alkali-soluble resin is SPC1001; in the step S5, the mass ratio of the salt-milled organic Pigment Red 254, the amine dispersant and the alkali-soluble resin is 1:0.3:2.5.

[0053] Example 2

[0054] A method for preparing a pigment red 254 coloring composition for color filters

[0055] The preparation method comprises:

[0056] S1. Bromination: Add the brominated salt to deionized water, stir and dissolve, then add benzyltriethylammonium bromide, dichloromethane and Pigment Red 254, heat to 180°C, pressure 3MPa, react for 8h, after the reaction is completed, separate the liquids, filter the organic phase, and then distill under reduced pressure to remove the solvent and impurities, and dry to obtain bromine-substituted Pigment Red 254;

[0057] S2, acrylate modification: acid binding agent and Pd 2 (dba) 3 Add toluene, stir for 10 minutes, add acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 under vacuum protection, react at 90°C for 3 hours, add to excess deionized water, separate the liquids, distill the organic phase under reduced pressure to remove the solvent, and dry to obtain acrylate-modified Pigment Red 254;

[0058] S3, preparation of organic pigment: after heating isopropanol to reflux, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone and sodium dodecylsulfonate are mixed and slowly added to isopropanol, and the reaction is continued for 6 hours after the addition is completed, and then the heating is stopped, and triethylamine is added after returning to room temperature, and after mixing evenly, the mixture is filtered, washed with deionized water for 3 times, and dried to obtain Organic Pigment Red 254;

[0059] S4, salt milling: adding the organic pigment Red 254, sodium chloride and diethylene glycol in a mass ratio of 1:12.5:5 to a kneader, and performing salt milling treatment at a speed of 80 rpm for 15 hours;

[0060] S5, sand milling: adding the organic pigment red 254 after salt milling, the amine dispersant and the alkali-soluble resin into a sand mill, sand milling at a rotation speed of 1500 rpm until the particles have a suitable particle size, and then stopping the sand milling to obtain the coloring composition.

[0061] The bromine salt is potassium bromide; the mass ratio of the bromine salt, deionized water, benzyl triethyl ammonium bromide and pigment red 254 in step S1 is 10:30:1:12.5; the acid binding agent is potassium carbonate; the acrylate monomer is ethyl acrylate; the acid binding agent, Pd 2 (dba) 3 , toluene, acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 are fed in a mass ratio of 10:0.2:80:5:2:10; in the step S3, the mass ratio of isopropanol, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is fed in a mass ratio of 100:8:0.1:0.1:2:30; the amine dispersant is BYK2001; the alkali-soluble resin is SPC3001; in the step S5, the mass ratio of the salt-milled organic Pigment Red 254, the amine dispersant and the alkali-soluble resin is 1:1:3.

[0062] Example 3

[0063] A method for preparing a pigment red 254 coloring composition for color filters

[0064] The preparation method comprises:

[0065] S1. Bromination: Add the bromide salt to deionized water, stir and dissolve, then add benzyltriethylammonium bromide, dichloromethane and Pigment Red 254, heat to 160°C, pressure to 2.5MPa, react for 6.5h, after the reaction is completed, separate the liquids, filter the organic phase, and then distill under reduced pressure to remove the solvent and impurities, and dry to obtain bromine-substituted Pigment Red 254;

[0066] S2, acrylate modification: acid binding agent and Pd 2 (dba) 3 Add toluene, stir for 8 minutes, add acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 under vacuum protection, react at 82°C for 2.5 hours, add to excess deionized water, separate the liquids, distill the organic phase under reduced pressure to remove the solvent, and dry to obtain acrylate-modified Pigment Red 254;

[0067] S3, preparation of organic pigment: after heating isopropanol to reflux, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone and sodium dodecylsulfonate are mixed and slowly added to isopropanol, and the reaction is continued for 4.5 hours after the addition is completed, and then the heating is stopped, and triethylamine is added after returning to room temperature. After mixing evenly, the mixture is filtered, washed with deionized water for 3 times, and dried to obtain Organic Pigment Red 254;

[0068] S4, salt milling: adding the organic pigment Red 254, sodium chloride and diethylene glycol in a mass ratio of 1:10:4 to a kneader, and performing salt milling at a speed of 70 rpm for 12 hours;

[0069] S5, sand milling: adding the salt-milled organic pigment Red 254, the amine dispersant and the alkali-soluble resin into a sand mill, sand milling at a rotation speed of 1200 rpm until the particles have a suitable size, and then stopping the sand milling to obtain the coloring composition.

[0070] The bromide salt is a combination of potassium bromide and sodium bromide in a mass ratio of 1:1; the mass ratio of bromide salt, deionized water, benzyltriethylammonium bromide and pigment red 254 in step S1 is 12:40:1.5:15; the acid binding agent is sodium tert-butoxide; the acrylate monomer is 2-methyl methacrylate; the acid binding agent, Pd 2 (dba) 3, toluene, acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 are fed in a mass ratio of 8:0.15:60:4:1.5:8; in the step S3, the mass ratio of isopropanol, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is 60:7:0.05:0.08:1.5:15; the amine dispersant is a combination of Lubrizol 20000, Lubrizol 32500 and BYK2001 in a mass ratio of 3:1:2; the alkali-soluble resin is SPC2000; in the step S5, the mass ratio of the salt-milled organic Pigment Red 254, the amine dispersant and the alkali-soluble resin is 1:0.5:2.8.

[0071] Example 4

[0072] A method for preparing a pigment red 254 coloring composition for color filters

[0073] The difference between this embodiment and embodiment 3 is that the acrylic acid ester monomer is 2-ethyl methacrylate, and the rest is the same as embodiment 3.

[0074] Example 5

[0075] A method for preparing a pigment red 254 coloring composition for color filters

[0076] The difference between this embodiment and embodiment 3 is that the amine dispersant is a combination of Lubrizol 20000, BYK2100 and EFKA4310 in a mass ratio of 1:1:1, and the rest is the same as embodiment 3.

[0077] Example 6

[0078] A method for preparing a pigment red 254 coloring composition for color filters

[0079] The difference between this embodiment and embodiment 3 is that the amine dispersant is a combination of Lubrizol 20000, BYK2200 and EFKA4030 in a mass ratio of 1:1:1, and the rest is the same as embodiment 3.

[0080] Example 7

[0081] A method for preparing a pigment red 254 coloring composition for color filters

[0082] The difference between this embodiment and embodiment 3 is that the alkali-soluble resin is a combination of SPC1001, SPC3001 and SPC2000 in a mass ratio of 1:1:1, and the rest is the same as embodiment 3.

[0083] Example 8

[0084] A method for preparing a pigment red 254 coloring composition for color filters

[0085] The difference between this embodiment and embodiment 3 is that the mass ratio of the organic pigment red 254, the amine dispersant and the alkali-soluble resin after salt grinding in step S5 is 1:1:2.5, and the rest is the same as embodiment 3.

[0086] Example 9

[0087] A method for preparing a pigment red 254 coloring composition for color filters

[0088] The difference between this embodiment and embodiment 3 is that the mass ratio of the organic pigment red 254, the amine dispersant and the alkali-soluble resin after salt grinding in step S5 is 1:0.3:3, and the rest is the same as embodiment 3.

[0089] Comparative Example 1

[0090] The difference between this comparative example and Example 3 is that Pigment Red 254 is not modified, but an equal amount of Pigment Red 254 is directly used to replace organic Pigment Red 254 for salt grinding and sand grinding to prepare a coloring composition, and the rest is the same as Example 3.

[0091] Test Example 1

[0092] Particle size analysis and testing of organic pigments in coloring compositions

[0093] The purpose of this test example is to determine the particle size distribution of the organic pigment in the coloring composition to evaluate the dispersibility and uniformity of the pigment: the particle size of the organic pigment in the coloring composition prepared in the embodiment and the comparative example is measured using a laser nanoparticle size analyzer, and the test results are shown in Table 1.

[0094] Table 1 Coloring composition particle size analysis test results

[0095] Test items Particle size D50(nm) Example 1 62.3 Example 2 65.4 Example 3 57.6 Example 4 68.5 Example 5 73.6 Example 6 82.5 Example 7 76.8 Example 8 86.5 Example 9 88.7 Comparative Example 1 100.5

[0096] It can be seen from the test results in Table 1 that the coloring composition prepared by the present invention shows significant advantages in the D50 particle size of the organic pigment. The D50 particle size of the organic pigment of the coloring composition of each embodiment is lower than that of the comparative example coloring composition, among which the D50 particle size of the coloring composition prepared in Example 3 is the smallest, that is, the process flow of Example 3 significantly reduces the particle size of the organic pigment. Through this modification, the agglomeration phenomenon of the pigment during the preparation process is effectively reduced, thereby effectively reducing the particle size of the organic pigment.

[0097] Test Example 2

[0098] Viscosity analysis of coloring composition

[0099] The purpose of this test example is to characterize the uniformity of the coloring composition by detecting the viscosity of the coloring composition at 25°C: the coloring composition is placed in a sample cell, and the viscosity of the coloring composition sample is measured at 25°C by a NDJ-9T coloring composition viscosity tester. Each group of examples is tested 3 times, and then the average value is taken. The results are shown in Table 2.

[0100] Table 2 Viscosity analysis results of coloring composition

[0101] Test items Viscosity / cp Example 1 6.5 Example 2 6.4 Example 3 6.2 Example 4 6.5 Example 5 6.6 Example 6 6.6 Example 7 6.5 Example 8 6.2 Example 9 6.2 Comparative Example 1 10.5

[0102] It can be seen from the test results in Table 2 that the coloring compositions prepared in various embodiments of the present invention have very low viscosity and good fluidity, and low viscosity can improve the uniformity and appearance quality of the coloring composition coating, improve the stability of the coloring composition, reduce pigment sedimentation and stratification, and enable the coloring composition to maintain good performance after long-term storage.

[0103] Test Example 3

[0104] Coloring composition filterability analysis test

[0105] The purpose of this test example is to detect the filterability of the coloring composition and verify the dispersibility of the pigment in the coloring composition: at -0.05MPa, filter membrane diameter 50mm, pore size 0.45μm polypropylene filter membrane, the time required to filter 200g of the coloring composition, the results are shown in Table 3.

[0106] Table 3 Filterability analysis results of coloring composition

[0107] Test items Filterability(min) Example 1 9.5 Example 2 8.1 Example 3 6.8 Example 4 7.2 Example 5 8.1 Example 6 6.5 Example 7 7.0 Example 8 7.2 Example 9 6.2 Comparative Example 1 20.5

[0108] It can be seen from the test results in Table 3 that the coloring composition of each embodiment has good filtration performance, which helps to evenly distribute the pigment in the coloring composition, form a more uniform coating thickness, avoid the phenomenon of uneven thickness of the pigment coating, ensure that there are no granular defects on the surface of the coating film, improve the gloss and touch of the paint film, thereby improving the appearance quality of the coating film, and the filterability also proves that the coloring composition prepared by the preparation method of the present invention ensures the dispersibility of the pigment in the coloring composition.

[0109] Test Example 4

[0110] Characterization of aging resistance of coloring compositions

[0111] The purpose of this test example is to characterize the aging resistance, stability and storage resistance of the coloring composition: the coloring composition prepared in each embodiment of the present invention and the comparative example is stored at 50°C for 90 days, and the particle size D50 and viscosity of the coloring composition before and after aging are measured to calculate the increase in particle size and viscosity. The aging resistance of the coloring composition is characterized, and the test results are shown in Table 4.

[0112] Table 4 Characterization results of aging resistance of coloring composition

[0113]

[0114]

[0115] It can be seen from the test results in Table 4 that the changes in particle size and viscosity after aging are significantly smaller than those in the unmodified comparative example 1, among which Example 3 shows the highest stability, proving that the coloring composition prepared by the present invention has good stability, reduces the aggregation and sedimentation of pigment particles during storage, thereby improving the stability and weather resistance of the coating during storage, and is convenient for transportation and long-term storage.

[0116] Test Example 5

[0117] Coloring composition contrast evaluation

[0118] The coated glass sheet was placed on a 120°C heating plate and heated for 90 seconds, and then heated in an oven at 230°C for 30 minutes. The chromaticity (x, y) was measured, and the contrast was measured using a contrast meter.

[0119] Table 5 Contrast evaluation results of coloring compositions

[0120]

[0121]

[0122] It can be seen from the test results in Table 5 that the present invention makes the prepared coloring composition less prone to agglomeration and stratification through modification, thereby improving the stability of the coloring composition and greatly improving the contrast of the coloring composition.

[0123] 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.

[0124] 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 pigment red 254 coloring composition for a color filter, characterized in that: include: S1. Bromination: Add the bromide salt to deionized water, stir and dissolve, then add benzyltriethylammonium bromide, dichloromethane and Pigment Red 254, heat to 150-180°C, pressure 2-3MPa, react for 5-8h, after the reaction is completed, separate the liquids, filter the organic phase, and then distill under reduced pressure to remove the solvent and impurities, and dry to obtain bromine-substituted Pigment Red 254; S2, acrylate modification: add an acid-binding agent and Pd2(dba)3 to toluene, stir for 5-10 minutes, add acrylate monomer, triethanolamine and bromine-substituted Pigment Red 254 under vacuum protection, react at 80-90°C for 1.5-3 hours, add to excess deionized water, separate the liquids, distill the organic phase under reduced pressure to remove the solvent, and dry to obtain acrylate-modified Pigment Red 254; S3, preparation of organic pigment: after heating isopropanol to reflux, acrylate-modified Pigment Red 254, azobisisobutyronitrile, hydroquinone and sodium dodecylsulfonate are mixed and slowly added to isopropanol, and after the addition is completed, the reaction is continued for 3-6 hours, and then the heating is stopped, and triethylamine is added after returning to room temperature. After mixing evenly, the mixture is filtered, washed with deionized water for 3 times, and dried to obtain Organic Pigment Red 254; S4, salt milling: adding the organic pigment red 254, sodium chloride and diethylene glycol in a mass ratio of 1:8-12.5:3-5 to a kneader, and performing salt milling treatment at a speed of 50-80 rpm for 10-15 hours; S5, sand milling: adding the salt-milled organic pigment Red 254, the amine dispersant and the alkali-soluble resin into a sand mill, sand milling at a rotation speed of 1000-1500 rpm until a suitable particle size is obtained, and then stopping sand milling to obtain the coloring composition.

2. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 1, characterized in that: The bromide salt is a combination of one or more of lithium bromide, potassium bromide, calcium bromide, sodium bromide, magnesium bromide, ferrous bromide, zinc bromide and copper bromide.

3. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 2, characterized in that: In the step S1, the mass ratio of the bromide salt, deionized water, benzyltriethylammonium bromide and Pigment Red 254 is 10-15:30-50:1-2.5:12.5-20.

4. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 3, characterized in that: The acid binding agent is one of sodium carbonate, potassium carbonate, cesium carbonate, sodium tert-butoxide and potassium tert-butoxide.

5. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 4, characterized in that: The acrylic acid ester monomer is one of methyl acrylate, ethyl acrylate, 2-methyl methacrylate and 2-ethyl methacrylate.

6. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 5, characterized in that: In the step S2, the mass ratio of the acid-binding agent, Pd2(dba)3, toluene, acrylate monomer, triethanolamine and bromine-substituted pigment red 254 is 5-10: 0.1-0.2: 50-80: 3-5: 1-2: 5-10.

7. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 6, characterized in that: In the step S3, the feed mass ratio of isopropanol, acrylate-modified pigment red 254, azobisisobutyronitrile, hydroquinone, sodium dodecylsulfonate and triethylamine is 50-100: 5-8: 0.01-0.1: 0.05-0.1: 0.5-2: 10-30.

8. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 7, 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.

9. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 8, characterized in that: The alkali-soluble resin is a combination of one or more of SPC1001, SPC3001 and SPC2000.

10. The method for preparing a pigment red 254 coloring composition for a color filter according to claim 9, characterized in that: The mass ratio of the organic pigment red 254, the amine dispersant and the alkali-soluble resin after salt grinding in step S5 is 1:0.3-1:2.5-3.

Images