Pyrrolopyrrole dione sulfonate compounds, preparation methods and applications thereof

Abstract

The present invention discloses a pyrrolopyrrolidione sulfonate compound, a preparation method thereof and an application thereof. The structural formula of the compound is shown as formula A or B below: The average particle size of the powder sample of the pyrrolopyrrolidione sulfonate compound of the present invention is less than 100 nm, and it has good dispersion performance for pigments. After mixing it with DPP powder, the crystallinity of the original DPP powder is increased, the crystal particles are finer and more concentrated, and the intermolecular force between the pigments is stronger, so that a better dispersion effect is produced.

Description

Technical Field

[0001] The present invention belongs to the technical field of chemical synthesis, and particularly relates to a pyrrolopyrrole dione sulfonate compound, a preparation method thereof, and uses thereof. Background Art

[0002] A commercial pigment always has complete crystallinity and crystal form, a concentrated particle size range and a complete shape. By adding additives or pigment derivatives to improve its surface properties, it still has good dispersion and excellent stability in the application system. As a well-known additive, pigment dispersants are widely used in the fields of pigments and dyes. Commonly used pigment dispersants can be divided into ionic, non-ionic and polymeric hyperdispersants. Ionic dispersants can be further divided into cationic, anionic and zwitterionic types.

[0003] The basic principle of dispersion is that the dispersant must be bound to the pigment particles in a certain form (anchoring effect) and provide steric hindrance, charge repulsion, etc. to maintain a stable dispersion state. The anchoring effect is mainly achieved by hydrogen bonding, polarization and van der Waals forces. Currently known dispersion theories include the double-layer theory and the steric hindrance theory. The model of the double-layer theory is that when a certain charge is given to the pigment surface, a charged ion cloud of the opposite charge will surround it. When two particles approach, the charge repulsion prevents them from approaching, thus preventing flocculation. Dispersants that can be explained by the double-layer theory contain charged groups such as carboxyl groups and sulfonic acid groups. The dispersant molecules of the steric hindrance theory have a pigmentophilic group at one end and a resin-compatible block at the other end. The dispersant molecules adsorb on the surface of the pigment particles by the pigmentophilic groups, and the resin-compatible chain segments dissolve in the resin solution, thus forming a steric hindrance around the pigment particles to prevent the particles from approaching.

[0004] The process of pigment dispersion generally includes three stages: wetting, dispersion and stabilization. The wetting stage refers to the process in which the gas on the surface of the pigment is replaced by the liquid during the dispersion in the liquid phase medium, that is, the process of forming a solid-liquid interface when the pigment particles contact the medium, which can generally be characterized by theoretical tests of surface tension and contact angle. The dispersion stage refers to the process in which the flocculated state of the pigment is broken into smaller particles under the action of mechanical energy to form a uniform and stable dispersion state; its theoretical tests can be characterized by light transmittance, particle size distribution, X-ray diffraction spectrum, transmission electron microscopy, etc. In the industrial field, tinting strength is widely used to judge whether the sample meets the industrial application standard. In the stabilization stage, the dispersant mainly maintains the stable dispersion state of the pigment, prevents the pigment from spontaneously flocculating, and promotes the suspension to obtain a stable state according to the type and molecular structure of the binder adsorbed on the pigment surface; it is mainly tested by some methods such as centrifugal stability test and freeze-thaw stability.

[0005] There are many reports on pigment dispersion at home and abroad. Most of the reports on pigment dispersants are some high molecular polymers: The research group of Jin Chul Kim published the characterization of the interaction between functional monomers such as styrene, butyl acrylate (BA), and ethyl 2-(N-phthalimido) methacrylate (PEMA) and the target dye (Disperse Blue 359). The research group of Jinying Yuan published the reversible addition-fragmentation chain transfer (RAFT) polymerization to synthesize three different structural types of novel polymeric dispersants, namely AB diblock, ABA triblock, and comb-like structures, and studied and compared the dispersion performance of SiO 2 particles in organic media. The research group of Fushao Hai published the preparation of a novel dispersant by the nucleophilic substitution reaction of RB4 and dodecan-1-ol, studied the dispersion performance of the novel dispersant on C.I. Pigment Blue 15:3, and applied the prepared dispersant as a novel dispersant in solvent-based inks, which showed good centrifugal stability and storage stability.

[0006] To sum up, there are relatively few studies on the direct derivative modification of small molecules on the pigment matrix. Summary of the Invention

[0007] In view of the above problems, the present invention provides a pyrrolopyrrole dione sulfonate compound, a preparation method thereof, and an application as an organic pigment dispersant. Specifically, the present invention provides a novel synthesis method of a small molecule pigment dispersant derived from a DPP pigment matrix, and relevant performance tests and stability tests are carried out on its dispersion characteristics.

[0008] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0009] In the first aspect of the present invention, a pyrrolopyrrole dione sulfonate compound is provided, and its structural formula is shown as Formula A or B below:

[0010]

[0011] Wherein: R 1 is selected from any one of the following structural formulas:

[0012]

[0013] -Cl, -Br, -F, -I, -CN, - t Bu, -CH 3 、-C 2 H 5 、-C 6 H 11 、-H, -CH 2 Cl, -OCH3 、 -NH 2 、 -OH, -SH;

[0014] X is selected from Li, Na or K.

[0015] Preferably, R 1 is - t Bu, -CH 3 、 -H, -CH 2 Cl, -OCH 3 、 -Cl, -Br, -F, -I, any one of them.

[0016] More preferably, the pyrrolopyrrole dione sulfonate compounds provided by the present invention are shown by any of the following structural formulas:

[0017]

[0018] The experimental results show that the average particle size of the samples of the pyrrolopyrrole dione sulfonate compounds of the present invention is less than 100 nm, and they have good dispersion performance for pigments; the XRD pattern shows that after mixing them with DPP powder, the crystallinity of the original DPP powder increases, and the crystal particles are finer and more concentrated; the transmission electron microscopy analysis shows that adding the DPP sulfonic acid group compound dispersant makes the intermolecular force between the pigments stronger, thus producing a better dispersion effect.

[0019] In the second aspect of the present invention, a preparation method of the above-mentioned pyrrolopyrrole dione sulfonate compounds is provided, and the reaction process is as follows:

[0020]

[0021] The reaction steps are as follows:

[0022] (1) Preparation of compound E

[0023] Sodium pellets and ferric chloride are successively added to tert-amyl alcohol, heated to 100 - 105 °C, reacted for 2 - 3 h, cooled to 50 - 60 °C, then compound D of benzonitrile is added, and then heated to 100 - 105 °C. A mixture of diisopropyl succinate compound C and tert-amyl alcohol is added dropwise, and finally reacted for another 2 - 5 h to stop the reaction; the reaction product is diluted with methanol, then the pH is adjusted to 7, filtered by suction, and then hot dissolved in N,N-dimethylformamide at 100 - 120 °C, and cooled and filtered by suction to obtain compound E;

[0024] (2) Preparation of compound A or B:

[0025] Compound E, 1,4-butanedisulfonate, a base and a suitable solvent with a molar ratio of 1:(2 - 6):(2 - 6) are mixed, heated and stirred for reaction for 4 - 10 h. After the reaction is completed, it is poured into an organic solvent to precipitate a solid, which is filtered and dried to obtain a crude product, and compound A or B is obtained through recrystallization.

[0026] Preferably, in the preparation process of compound E, (1) the volume - mass ratio of tert - butyl alcohol, sodium pellets and ferric chloride is: 100 mL:2 - 4 g:20 - 40 mg; the molar ratio of benzonitrile compound D to sodium pellets is (0.3 - 0.5):1; the molar ratio of diisopropyl succinate compound C to sodium pellets is (0.15 - 0.3):1, and the molar ratio of benzonitrile compound D to diisopropyl succinate compound C is 1:1; the mixture of diisopropyl succinate compound C and tert - amyl alcohol is added dropwise within 2 - 3 h. (2) The pH of the initial reaction product is adjusted to 7 with acetic acid; after the first filtration, the filter cake is washed with methanol and water, and then heated and dried; after the second filtration, the filter cake is washed with water and methanol in sequence, and then heated and dried.

[0027] Preferably, in the preparation process of compound A or B, the molar ratio of compound E, 1,4 - butanedisulfonate and a base is 1:5:5 - 1:1:5; the base used is potassium tert - butoxide or sodium tert - butoxide, the solvent is dimethyl sulfoxide, and the organic solvent is acetonitrile.

[0028] In the third aspect of the present invention, the application of the above - mentioned pyrrolopyrrole dione sulfonate compounds is provided, specifically the application in the preparation of a pigment dispersant.

[0029] Preferably, the pigment is an organic pigment, and more preferably a DPP pigment.

[0030] In the fourth aspect of the present invention, an organic pigment dispersant is provided, which includes an active ingredient and auxiliary materials, and the active ingredient is the above - mentioned pyrrolopyrrole dione sulfonate compound.

[0031] The beneficial technical effects of the present invention:

[0032] In terms of effects, the pyrrolopyrrole dione sulfonate compounds of the present invention have good application in the dispersion of organic pigments. Only a small amount of the above - mentioned compounds needs to be added to pigment DPP - 254, and excellent dispersion characteristics are shown. The pigment dispersions prepared by adding the compounds of the present invention are compared with the blank sample for X - ray diffraction test and transmission electron microscopy test. The results show that the particle size distribution of the pigment powder added with the compounds of the present invention is more uniform and the crystallinity is better, indicating that the compounds of the present invention show excellent dispersion performance in pigment DPP - 254.

[0033] In terms of preparation technology, the preparation method of the pyrrolopyrrole dione sulfonate compound of the present invention is simple, does not require harsh reaction conditions, and is conducive to subsequent scale-up tests or production. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 Pre-dispersion diagram of pigment dispersions prepared by adding pigment DPP-254 to compound A-1, B-1, A-2, B-2, A-3, and B-3 powders and blank samples in deionized water;

[0035] Figure 2 A schematic diagram showing the relationship between the X-ray diffraction test of the pigment dispersion prepared by adding the pigment DPP-254 to the compounds A-1 and B-1 and the blank sample;

[0036] Figure 3 Schematic diagram of the molecular distribution of the pigment dispersion prepared by adding pigment DPP-254 to compound A-1 and the blank sample tested by scanning electron microscopy at a magnification of 58,000 times. DETAILED DESCRIPTION

[0037] In order to explain the present invention more clearly, the present invention is further described below in conjunction with preferred embodiments. It should be understood by those skilled in the art that the following specific description is illustrative rather than restrictive, and should not be used to limit the scope of protection of the present invention.

[0038] The reagents used in the examples of the present invention are as follows:

[0039] Tert-amyl alcohol (manufacturer: Shanghai McLean Biochemical Technology Co., Ltd., specification: 500ml, purity: 98%), metallic sodium (manufacturer: Sinopharm Chemical Reagent Co., Ltd., specification: 250g, purity: 99%), ferric chloride (manufacturer: Shanghai Bailingwei Chemical Technology Co., Ltd., specification: 25g, purity: 99%), benzonitrile (manufacturer: Shanghai Mairui Chemical Technology Co., Ltd., specification: 100g, purity: 99%), diisopropyl succinate (manufacturer: Shanghai Mairui Chemical Technology Co., Ltd., specification: 500g, purity: 99%), acetic acid (manufacturer: Shanghai Mairui Chemical Technology Co., Ltd. , specification: 500mL, purity: 99%), N,N-dimethylformamide (Manufacturer: Shanghai Titan Technology Co., Ltd., specification: 500mL, purity: 99%), methanol (Manufacturer: Titan Technology Co., Ltd., specification: 25L, purity: 99%), acetonitrile (Manufacturer: Shanghai Titan Technology Co., Ltd., specification: 25L, purity: 99%), potassium tert-butoxide (Manufacturer: Shanghai Boer Chemical Reagent Co., Ltd., specification: 500g, purity: 99%), 1,4-butanesulfonic acid ester (Manufacturer: Shanghai Dibai Chemical Technology Co., Ltd., specification: 25g, purity: 99%).

[0040] Example 1

[0041]

[0042] Add 4 g of sodium pellets to 100 ml of tert-amyl alcohol, then add 30 mg of ferric chloride, heat to 105 °C, react for 2 h, cool to 50 °C, add (80 mmol, 12.7 g) p-tert-butylbenzonitrile D1, and then heat to 105 °C. Mix (40 mmol, 8 g) diisopropyl succinate compound C with 30 mL of tert-amyl alcohol mixture and add dropwise at 3 - 5 drops / s for 3 h. Finally, react for another 4 h to stop the reaction. Pour the reaction product into a 1000 ml beaker, dilute with a large amount of methanol, adjust the pH to 7 with acetic acid, filter by suction, wash the filter cake with methanol and water, take the filter cake, heat and dry it, then dissolve it in N,N-dimethylformamide at 120 °C, cool and filter by suction, wash the filter cake with water and methanol in sequence, take the filter cake, heat and dry it to obtain compound E1 (yield: 55%);

[0043]

[0044] Mix (10 mmol, 4.0 g) E-1, (50 mmol, 5.6 g) potassium tert-butoxide and 40 ml of dimethyl sulfoxide, heat to 80 °C to abstract hydrogen for half an hour, then add (50 mmol, 6.8 g) 1,4-butanesultone and stir for 6 h. After the reaction is completed, cool to room temperature, pour it into 300 ml of acetonitrile solvent to precipitate solids, filter by suction and dry to obtain the crude product, and recrystallize with methanol to obtain compound A-1 (yield: 78%).

[0045] The test results of A-1 are as follows:

[0046] 1 H NMR(400MHz,Methanol-d4)δ7.80(d,J=8.5Hz,4H),7.63(d,J=8.5Hz,4H),3.81(t,J=6.5Hz,4H),2.73(t,4H),1.75–1.67(m,8H),1.37(s,18H).

[0047] 13 C NMR(151MHz,DMSO-d6)δ162.83(s),162.07(s),154.69(s),148.06(s),128.98(s),126.29(s),108.82(s),51.22(s),35.33(s),31.34(s),28.71(s),22.92(s).

[0048] HRMS(TOF-ESI): m / z[M / 2] +: Calculated for C16H22NO4S + : 335.6231; Found: 335.6229.

[0049]

[0050] (10 mmol, 4.0 g) of E-1, (50 mmol, 5.6 g) of potassium tert-butoxide and 40 ml of dimethyl sulfoxide were mixed, heated to 80 °C for dehydrogenation for half an hour, then (10 mmol, 1.4 g) of 1,4-butanesultone was added and stirred for reaction for 6 h. After the reaction was completed, it was cooled to room temperature, poured into 300 ml of acetonitrile solvent to precipitate a solid, filtered by suction and dried to obtain a crude product, which was recrystallized from methanol to obtain compound B-1 (yield: 85%).

[0051] The test results of B-1 are as follows:

[0052] 1 H NMR (400 MHz, DMSO-d6) δ 11.23 (s, 1H), 8.42 (d, J = 8.1 Hz, 2H), 7.79 (d, J = 7.9 Hz, 2H), 7.59 (d, 4H), 3.80–3.71 (m, 2H), 2.39–2.33 (m, 2H), 1.58–1.47 (m, 4H), 1.33 (s, 18H).

[0053] 13 C NMR (151 MHz, DMSO-d6) δ 162.04 (s), 155.87 (s), 154.37 (s), 145.94 (s), 128.96 (s), 128.42 (s), 126.48 (s), 126.27 (s), 110.94 (s), 108.46 (s), 51.31 (s), 41.77 (s), 35.49 (s), 35.35 (s), 31.41 (s), 28.82 (s), 22.99 (s).

[0054] HRMS (TOF-ESI): m / z [M] + : Calculated for C30H35N2O5S + : 535.2267; Found: 535.2266.

[0055] Example 2

[0056]

[0057] The synthesis procedure of compound E-2 is similar to that of compound E-1 in Example 1, except that benzonitrile (8.2 g, 80 mmol) is used instead of tert-butylbenzonitrile for synthesizing compound D-1 in Example 1. The remaining synthesis steps are the same as those in Example 1, and the amounts of each compound are also the same as those in Example 1 (yield: 58%).

[0058]

[0059] The preparation of compound A-2 was carried out with reference to Example 1, and the amounts of each compound were also the same as those in Example 1 (yield: 75%). The relevant data of compound A-2 are shown below:

[0060] 1H NMR(600MHz,DMSO-d6)δ7.88–7.82(m,4H),7.63–7.58(m,6H),3.68(t,J=7.2Hz,4H),2.28(t,J=7.4Hz,4H),1.63–1.35(m,6H).

[0061] 13C NMR(151MHz,DMSO-d6)δ161.93(s),148.33(s),131.72(s),129.39(s),129.07(s),128.18(s),109.08(s),51.18(s),41.35(s),28.60(s),22.91(s).

[0062] HRMS(TOF-ESI):m / z[M / 2] + :calcd for C13H14NO4S:279.5605;Found:279.5600。

[0063]

[0064] The preparation of compound B-2 was carried out with reference to Example 1, and the amounts of each compound were also the same as those in Example 1 (yield: 85%). The relevant data of compound B-2 are shown below:

[0065] 1 H NMR(400MHz,DMSO-d6)δ7.86–7.79(m,2H),7.63–7.55(m,2H),7.49–7.40(m,6H),3.91–3.82(m,2H),3.29–3.11(m,2H),1.90–1.78(m,4H);

[0066] 1313C NMR (151 MHz, DMSO-d6) δ 162.02 (s), 160.61 (s), 159.08 (s), 152.75 (s), 133.04 (s), 132.74 (s), 128.77 (s), 128.52 (s), 128.34 (s), 128.01 (s), 127.07 (s), 124.33 (s), 120.20 (s), 54.76 (s), 44.45 (s), 27.47 (s), 20.18 (s);

[0067] HRMS (TOF-ESI): m / z [[M]] + : calcd for C22H19N2O5S + : 423.1015; Found: 423.1018.

[0068] Example 3

[0069]

[0070] The synthesis procedure of compound E-3 was similar to that of compound E-1 in Example 1, except that the tert-butylbenzonitrile used for synthesizing compound D-1 in Example 1 was replaced with p-chlorobenzonitrile (11.0 g, 80 mmol), and the remaining synthesis steps were the same as those in Example 1, and the dosages of each compound were also the same as those in Example 1 (yield: 57%).

[0071]

[0072] (10 mmol, 3.6 g) of E-3, (50 mmol, 5.6 g) of potassium tert-butoxide and 40 ml of dimethyl sulfoxide were mixed, and the temperature was raised to 80 °C to abstract hydrogen for half an hour. Then, (50 mmol, 6.8 g) of 1,4-butanesultone was added and stirred for reaction for 6 h. After the reaction was completed, it was cooled to room temperature, poured into 300 ml of acetonitrile solvent to precipitate a solid, filtered by suction and dried to obtain a crude product, which was recrystallized from methanol to obtain compound A-3 (yield: 75%).

[0073] The test results of A-3 are as follows:

[0074] 1 1H NMR (400 MHz, Methanol-d4) δ 8.38 (d, J = 8.7 Hz, 2H), 7.85 (d, J = 8.6 Hz, 2H), 7.58 (dd, J = 12.2, 8.7 Hz, 4H), 3.88 (s, 1H), 2.86 (s, 2H), 1.72 (s, 4H), 1.29 (d, J = 3.6, 12H).

[0075] 13 13C NMR (151 MHz, DMSO-d6) δ 167.24 (s), 152.37 (s), 139.17 (s), 134.48 (s), 132.40 (s), 131.25 (s), 113.80 (s), 59.63 (s), 48.11 (s), 29.70 (s), 24.66 (s).

[0076] HRMS (TOF-ESI): m / z [M - 2K] 2+ : 2 calculated for [C 26 H 24 Cl 2 N 2 O 8 S 2 + / 2, 313.0176; Found: 313.0198.

[0077]

[0078] (10 mmol, 3.6 g) of E-1, (50 mmol, 5.6 g) of potassium tert-butoxide and 40 ml of dimethyl sulfoxide were mixed, heated to 80 °C for half an hour to abstract hydrogen, then (10 mmol, 1.4 g) of 1,4-butanesultone was added and stirred for reaction for 6 h. After the reaction was completed, it was cooled to room temperature, poured into 300 ml of acetonitrile solvent to precipitate a solid, filtered by suction and dried to obtain a crude product, which was recrystallized from methanol to obtain compound B-3 (yield: 84%).

[0079] The test results of B-3 are as follows:

[0080] 1 1H NMR (400 MHz, Methanol-d4) δ 8.54 (d, J = 8.0 Hz, 2H), 7.88 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 8.0 Hz, 4H), 6.70 (s), 2.35 (d, 4H), 1.46 (m, 4H);

[0081] 13 13C NMR (151 MHz, DMSO-d6) δ 167.75 (s), 166.15 (s), 152.15 (s), 150.18 (s), 139.14 (s), 139.07 (s), 134.21 (s), 133.14 (s), 133.11 (s), 132.42 (s), 131.88 (s), 131.27 (s), 115.09 (s), 114.96 (s), 59.64 (s), 48,12 (s), 29.71 (s), 24,67 (s).

[0082] HRMS (TOF - ESI): m / z [M - K] + : calcd for C 22 H 17 C l2 N 2 O 5 S + : 491.02; Found: 491.02367.

[0083] Example 4

[0084] Weigh 10 mg of the product powders A - 1, B - 1, A - 2, B - 2, A - 3, and B - 3 in Example 1 and place them in a test tube. Then add 0.1 g of Pigment Red 254 (Pigment DPP - 254, the same below) powder to it. Next, add 10 ml of deionized water, shake twice, and ultrasonicate for 30 min. After ultrasonication, place it on a test tube rack, as Figure 1 shown. In the blank sample of Test Tube 1, Pigment Red 254 powder is added. In Test Tube 2, A - 1 and pigment powder are added. In Test Tube 3, B - 1 and pigment powder are added. In Test Tube 4, A - 2 and pigment powder are added. In Test Tube 5, B - 2 and pigment powder are added. In Test Tube 6, A - 3 and pigment powder are added. In Test Tube 7, B - 3 and pigment powder are added. It can be seen from Figure 1 that compared with the blank sample, the samples added with A - 1, B - 1, A - 2, B - 2, A - 3, and B - 3 powders all have good dispersion performance for Pigment Red 254 in the water system.

[0085] Next, the particle size distributions of Test Tubes 2, 3, 4, 5, 6, and 7 were tested using a particle size analyzer, as shown in Table 1.

[0086] Table 1 Summary of the average particle sizes of the samples added with A - 1, B - 1, A - 2, B - 2, A - 3, and B - 3 powders

[0087]

[0088] As can be seen from Table 1, the average particle sizes of the samples added with A - 1, B - 1, A - 2, B - 2, A - 3, and B - 3 powders are 79.02 nm, 64.84 nm, 88.11 nm, 84.24 nm, 92.52 nm, and 82.47 nm respectively. This further shows that Compounds A - 1 and B - 1 have good dispersion performance for Pigment Red 254 and are a type of new pigment dispersant with good performance.

[0089] Example 5

[0090] Compound A-1 and B-1 were added to Pigment Red 254 used at an addition amount of 5 wt% of the weight of Pigment Red 254 used. An appropriate amount of water was added for pulping treatment, followed by filtration and drying. A small amount of the dried powder was taken for X-ray diffraction testing (XRD), and the test results are as Figure 2 shown.

[0091] For crystalline materials, when the crystal to be measured makes different angles with the incident beam, those crystal planes that satisfy Bragg diffraction will be detected, which are manifested as diffraction peaks with different diffraction intensities on the XRD pattern. It can be seen from the XRD test results that the addition of dispersants A-1 and B-1 has certain effects on the crystal form and crystallinity of Pigment Red 254. Their addition increases the crystallinity of the original DPP powder, and the crystal form particles are finer and more concentrated. It also proves that the addition of these two additives greatly improves the dispersion performance of Pigment Red 254.

[0092] Example 6

[0093] The samples of A-1 + Pigment Red 254 after pulping and drying and the blank sample of Pigment Red 254 were subjected to field emission transmission electron microscopy testing, as Figure 3 shown. The left side is the blank sample, and the right side is the sample with Compound A-1 added. It can be seen from Figure 3 that on the right side where Compound A-1 is added, the molecules are more divergent from each other and the diameter of each molecule is a little smaller, while on the left side, the molecules are aggregated together and the flocculation phenomenon is more serious. From the transmission electron microscopy analysis, the addition of the DPP sulfonic acid group compound dispersant makes the intermolecular force between the pigments stronger, resulting in better dispersion. Thus, it can be known that the pyrrolopyrrole dione sulfonic acid group compound is a potential new type of high-performance pigment dispersant, and has excellent dispersion effect on Pigment Red 254.

[0094] The above description is only a preferred embodiment of the present invention, and does not impose any form of limitation on the present invention. Although the present invention has been disclosed above with the preferred embodiment, it is not intended to limit the present invention. Any person skilled in the art of this patent, without departing from the scope of the technical solution of the present invention, can make some changes or modifications to the above-mentioned technical content as equivalent embodiments of equivalent changes. However, as long as it does not depart from the content of the technical solution of the present invention, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention still fall within the scope of the present invention.

Claims

1. A pyrrolopyrrole dione sulfonate compound, characterized in that: The structural formula is as shown below: X is selected from K, R 1 is selected from tert-butyl group.

2. The preparation method of the pyrrolopyrrole dione sulfonate compound according to claim 1, characterized in that The reaction process is as shown below: The reaction steps are as follows: (1) Preparation of compound E Sodium pellets and ferric chloride are successively added to tert-amyl alcohol, heated to 100 - 105 °C, reacted for 2 - 3 h, cooled to 50 - 60 °C, then benzonitrile compound D is added, and then heated to 100 - 105 °C. A mixed solution of diisopropyl succinate compound C and tert-amyl alcohol is added dropwise, and finally reacted for another 2 - 5 h to stop the reaction; the reaction product is diluted with methanol, then the pH is adjusted to 7, filtered by suction, and then hot dissolved in N,N-dimethylformamide at 100 - 120 °C, and cooled and filtered by suction to obtain compound E; (2) Preparation of compound A or B-1: Compound E, 1,4-butanesultone, potassium tert-butoxide and a suitable solvent with a molar ratio of 1:(2 - 6):(2 - 6) are mixed, heated and stirred for 4 - 10 h. After the reaction is completed, it is poured into an organic solvent to precipitate a solid, filtered by suction and dried to obtain a crude product, which is recrystallized to obtain compound A or compound B-1. wherein, R 1 is selected from tert-butyl, and X is selected from K.

3. The preparation method of the pyrrolopyrrole dione sulfonate compound according to claim 2, characterized in that: Among them, In the preparation process of compound E, the volume-mass ratio of tert-amyl alcohol to sodium pellets and ferric chloride is: 100 mL: 2 - 4 g: 20 - 40 mg; the molar ratio of benzonitrile compound D to sodium pellets is (0.3 - 0.5):1; the molar ratio of diisopropyl succinate compound C to sodium pellets is (0.15 - 0.3):1, and the molar ratio of benzonitrile compound D to diisopropyl succinate compound C is 1:1; the mixed solution of diisopropyl succinate compound C and tert-amyl alcohol is added dropwise within 2 - 3 h. The pH of the reaction product is adjusted to 7 with acetic acid. After the first filtration by suction, the filter cake is washed with methanol and water, and then heated and dried; after the second filtration by suction, the filter cake is washed with water and methanol in turn, and then heated and dried.

4. The preparation method of the pyrrolopyrrole dione sulfonate compound according to claim 2, characterized in that: Among them, In the preparation process of compound A or B-1, the molar ratio of compound E, 1,4-butanesultone, and base is 1:5:5 - 1:1:5; The solvent is dimethyl sulfoxide, and the organic solvent is acetonitrile.

5. The application of the pyrrolopyrrole dione sulfonate compound according to claim 1 as a dispersant for pigment DPP-254.

6. An organic pigment dispersant, characterized in that It includes an active ingredient and auxiliary materials, and the active ingredient is the pyrrolopyrrole dione sulfonate compound according to claim 1.

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