CN109627490B - Red organic colorant applied to resin coloring and preparation method thereof - Google Patents
Red organic colorant applied to resin coloring and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a red organic colorant applied to resin coloring and a preparation method thereof, and the red organic colorant has a structural general formula shown as I:
Description
Technical Field
The invention belongs to the field of organic coloring agents, and particularly relates to a high-temperature-resistance, migration-resistance and easy-dispersion red organic coloring agent applied to resin coloring and a preparation method thereof.
Background
The development of material science has higher and higher requirements on the performance of the colorant, and has higher requirements on the temperature resistance, the migration resistance in resin and the dispersibility of the colorant besides excellent weather resistance, light resistance and various chemical resistances. One part of the organic colorant is various dyes and solvent dyes with certain water solubility or solvent solubility, and the other part is pigment which is insoluble in water and various application media. The resin coloring can be only solvent dyes and pigments, and water-soluble dyes cannot be used. Although such colorants are commercially available, they all have certain drawbacks for use in coloring resins. Such as: solvent dyes have good tinctorial properties and are dissolved and dispersed in resins, but color bleeding occurs during the coloring process or during the leaving of the colored object, i.e., poor migration resistance. The organic pigment has bright color and good performance, does not migrate, but is difficult to disperse into an application medium in application due to compact crystal structure and easy aggregation, and particularly has the problem of blockage in high-precision coloring, such as in the field of fiber stock solution coloring, the field of digital spray painting and the like, and the color reducibility is poor, so that the coloring effect of the dye is difficult to achieve.
There are many colorants containing anthrapyridone structure disclosed in the prior art, wherein there are 4 colorants related to solvent dye, which are c.i. solvent red 52, c.i. solvent red 149, c.i. solvent red 150, and c.i. solvent red 151, respectively;
the structural colorant has bright color, high tinting strength and good temperature resistance (280 ℃), and can be colored by thermoplastic resin. However, since the molecular weight is small, the solubility in a solvent is high, and the resin cannot be applied to high-quality products, particularly PET and PA resins with high processing temperature, color migration occurs, namely, the migration resistance is poor.
In recent years, there have been many reports of research on the development of colorants around the anthrapyridone structure, such as: the publication of 2003 in the journal of "dyes and dyeings" by yiyi et al, yosu, aolunda scientific and technical practice, inc, uses halogenated anthrapyridone as a main raw material, and condenses with ammonia, monomethylamine, monoethylamine, n-propylamine, n-butylamine, ethanolamine, p-toluidine, 3, 4-dimethylaniline, p-methoxyaniline, o-isopropylaniline, m-isopropylaniline, p-isopropylaniline, n-butylaniline, p-tert-butylaniline, cyclohexylamine, and sixteen amines of benzylamines to obtain the corresponding dyes, and the solubility of the synthesized dyes was measured, leading to the conclusion: the solubility of the synthesized sixteen compounds in the organic solvent is increased along with the reduction of the polarity of the solvent; the solubility gradually increases with increasing carbon chain.
Chinese patent CN 101535269a discloses a thermostable colorant related to anthrapyridone compounds, which can be used for coloring polycarbonate articles and has excellent heat resistance, light resistance and color bleeding resistance. Two novel structural anthrapyridone compounds are disclosed as follows.
Four novel anthrapyridone magenta dyes are synthesized by the university of great colligation Master academic thesis, Lishiyu and the like, and the dyes have good light-resistant stability. The four-branch dye is a water-soluble dye and has the following structure:
the research surrounding the increase of molecular structure mainly comes from the reports in japan.
Japanese patent JP 2003-192930A in 2003 discloses a magenta dye with an anthrapyridone structure, wherein R is selected from a hydrogen atom, an alkyl group or a cyclohexyl group, Y is selected from a hydrogen atom, a hydroxyl group, an amino group, a mono-or dialkylamino group, an alkoxy group, a phenylamino group, a phenoxy group, an aralkyl or cycloalkylamino group, a naphthylamino group and the like, and X is selected from ethylenediamine, butanediamine, hexamethylenediamine and the like, and the compound has excellent fastness in light resistance, water resistance and the like.
JP 2012-126770A published in 2012 by Japanese chemists discloses a novel anthrapyridone compound, the structure of which is as follows, the group X is ethylenediamine tetraacetic dianhydride, and the compound has high-definition color tone and is excellent in light resistance and weather fastness.
However, the research still adopts water-soluble dyes, and the main application field is digital painting. And the bridge group of the symmetrical part is a flexible chain segment and does not have a rigid structure, so that a certain degree of crystallinity cannot be formed, and the problem of resin coloring is difficult to solve.
Disclosure of Invention
The invention aims to provide a red organic colorant with novel structure and applied to resin coloring and a preparation method thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a red organic colorant for coloring resin is disclosed, which is a compound represented by general formula I,
general formula I
In the formula:
r is selected from hydrogen and C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a).
Preferably, R in the general formula I is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, chlorine or bromine.
More preferably, R in the general formula I is selected from hydrogen, methyl or chlorine.
A preparation method of a red organic colorant applied to resin coloring,
the method comprises the following steps: reaction formula is
Wherein: x is selected from Cl and Br;
r is selected from-H, C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a);
6-X-N-methyl-anthrapyridone (6-X-3-methyl-3H-naphtho [1,2,3-de ] quinoline-2,7-dione) and 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine are mixed, and the mixture is subjected to Ullmann condensation reaction in a high boiling point organic solvent in the presence of a catalyst and an acid-binding agent to obtain the compound shown in the general formula I.
Further, the 6-X-N-methyl-anthrapyridone and the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine are mixed and subjected to Ullmann condensation reaction for 10-12h at 160-180 ℃ in a high-boiling-point organic solvent in the presence of a catalyst and an acid-binding agent to obtain a compound shown in the general formula I; wherein the mol ratio of the 6-X-N-methyl-anthrapyridone to the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine is 2:1, the weight ratio of the high-boiling-point organic solvent to 6-X-N-methyl-anthrapyridone is 10-13: 1, the molar ratio of the acid-binding agent to 6-X-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to 6-X-N-methyl-anthrapyridone is 1: 14-16.
The second method has the reaction formula
The compound of the general formula I is obtained by carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high boiling point organic solvent in the presence of an acid binding agent and a catalyst.
Further, 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine are subjected to Ullmann condensation reaction for 10 to 12 hours at the temperature of 160-170 ℃ in a high-boiling-point organic solvent in the presence of an acid binding agent and a catalyst to obtain a compound shown in the general formula I; wherein the mol ratio of the 6-amino-N-methyl-anthrapyridone to the 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine is 2:1, and the weight ratio of the high boiling point organic solvent to the 6-amino-N-methyl-anthrapyridone is 11-13: 1, the molar ratio of the acid-binding agent to the 6-amino-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to the 6-amino-N-methyl-anthrapyridone is 1: 14-16.
The starting materials in the synthesis method of the second method can be obtained by synthesis in the prior literature, such as the literatures SU 1016283 and s.von anger.product subglasses 3: 1,3, 5-triazines and phosphor alloys [ J ]. Science of Synthesis,2004,1(7):449-583. mention the Synthesis of the starting materials.
In the two synthesis methods, the catalyst is selected from copper powder, cuprous chloride, cuprous iodide, cupric acetate or cupric sulfate, preferably cuprous chloride or cuprous iodide; the acid-binding agent is alkali metal carbonate or alkali metal bicarbonate; alkali metal bicarbonates are preferred.
In the above process-the high-boiling organic solvent is usually dichlorobenzene, nitrobenzene, dimethyl sulfoxide, N-methylpyrrolidone or alkylbenzene.
In the second method, the inert organic solvent is dichlorobenzene, nitrobenzene, dimethyl sulfoxide or alkylbenzene.
In the two synthesis methods, after Ullmann condensation reaction, the product is subjected to heat treatment by a polar organic solvent and particle size adjustment to obtain the red powdery compound with the general formula I and a soft structure, so that the red powdery compound is convenient for subsequent application and dispersion, and the cost for recovering the solvent can be reduced.
The polar organic solvent is alcohols, N-dimethylformamide, dimethyl sulfoxide and the like; alcohol organic solvents are preferred. Wherein the alcohol can be methanol, ethanol, n-butanol, isobutanol, amyl alcohol, tertiary amyl alcohol, octanol, etc. Butanol is more preferable.
The two synthetic methods described above are preferred from the viewpoint of ease of preparation and availability of raw materials.
The application of the compound in the general formula I as a coloring agent for resin is disclosed.
The resin may be PE, PP, PET, PC, PA ABS resin, PS resin, PMMA, or the like. Can be used for preparing color master batches, coloring fiber stock solution, plastic films, plastic printing or injection molding and other fields. The beneficial effects of the invention are highlighted as follows:
1. the invention is suitable for resin coloring organic colorants which are bright yellow red, have a melting point of 320 ℃, show obvious crystallinity by XRD analysis and show fine rod-like crystals by electron microscopy. The coloring agent has soft particles, and has obvious easy dispersibility compared with the traditional organic pigment by adopting a scraper fineness instrument to detect the easy dispersibility of the coloring agent.
2. The colorant is subjected to temperature resistance test, a PET resin injection molding method is adopted, the injection molding condition is an organic pigment limit detection condition in the field, namely, the retention time is 5 minutes at 300 ℃, C.I. pigment yellow 147 with good temperature resistance recognized in the field of fiber stock solution coloring is taken as a reference standard, the colorant has remarkable advantages in color change and color difference value, and has better temperature resistance than the C.I. pigment yellow 147.
3. The resistance test is carried out by adopting a national standard method, the rating standard is optimally 5 grades, the worst is 1 grade, the colorant related to the invention shows 5 grades of resistance in different polar organic solvents, and the acid and alkali resistance of the colorant is 5 grades, so that the colorant shows excellent solvent resistance and chemical resistance.
In conclusion, the compound of the general formula I is an organic colorant, has a novel structure, is bright yellow red, has good heat resistance, solvent resistance and easy dispersibility, can meet the requirements of temperature resistance and migration resistance in coloring of high-temperature processed resin such as PET and the like, and has loose and soft particles and good easy dispersibility. The product can be used as a colorant for resin, can be used in the fields of color master batches, fiber stock solution coloring, plastic films, plastic printing or injection molding and the like, meets the application requirements of PE, PP, PET, PC, PA ABS resin, PS resin, PMMA and the like, and has potential commercial value.
Drawings
FIG. 1 is a transmission microtopography under an optical microscope of a colorant provided in example 1 of the present invention.
FIG. 2 is a scanning microtopography of a colorant provided in example 1 of the present invention under an electron microscope.
FIG. 3 is an XRD analysis of a colorant according to the present invention.
Detailed Description
The following examples serve to illustrate the invention in further detail. In the examples, parts and percentages are by weight unless otherwise indicated.
The poor migration of colorants known to those skilled in the art is generally due to the colorant's solubility in the application medium, and supersaturation precipitation occurs as application conditions change; or the colorant has poor temperature resistance, and is decomposed and sublimated in high-temperature application to cause color overflow. Temperature resistance and solvent resistance are therefore important conditions for evaluating the migration resistance of coloring. Dispersibility is due to the molecular polarity, planarity and symmetry of the compound which affects the growth and aggregation of its nascent structure, and thus affects the size and hardness of the colorant's crystal form and aggregates. The invention provides a compound with a novel structure, which connects an anthrapyridone structure with moderate molecular polarity and good temperature resistance into a compound with larger molecular weight by taking a triazine structure compound as a bridging group. The compound keeps the excellent temperature resistance characteristic of an anthrapyridone structure, and the solvent resistance characteristic is ensured due to the increase of the molecular weight, so that the migration resistance of the compound is ensured; meanwhile, the rigidity of the large molecular structure is enhanced but the structural connection of the bridge group triazine does not have planarity, and although the whole molecular structure has symmetry and rigidity, the growth of crystals and the growth and aggregation of nascent particles are still influenced due to poor planarity, so that the compound particles are soft and easy to disperse in an application medium, and have better dispersibility.
The anthrapyridone compound shown in the general formula I is characterized by bright yellow red color and excellent heat resistance, and the injection molding test of staying at 300 ℃ of PET resin for 5min, the bleeding test of solvents such as ethanol, ethyl acetate, N-dimethylformamide, dimethyl sulfoxide and the like, and the acid and alkali treatment test prove that the compound shown in the general formula I can be used for coloring the resin under the high-temperature condition, and the color can not be shifted due to the high-temperature injection molding condition and the polarity of the resin, a plasticizer and the like. Meanwhile, the compound of the general formula I has soft particles, is easy to disperse, is a colorant with potential commercial value, can be used for coloring PE PP PET, PA ABS and other resins, and can also be used for coloring stock solution of polyester, polypropylene, acrylic fiber, spandex and other fibers.
Preparation examples
Example 1
The reaction formula is as follows:
wherein: x is selected from Br; r is selected from-H.
In a 250mL four-necked flask, 7.1 parts of 6-bromo-N-methyl-anthrapyridone, 1.87 parts of benzoguanamine, 0.42 part of cuprous iodide, and 90 mL of alkylbenzene were charged. Heating to 170 ℃, keeping the temperature for reaction for 30 minutes, then gradually adding 2.1 parts of sodium bicarbonate in portions, adjusting the pH value of the reaction, and reacting for 12 hours at the temperature of 165-170 ℃. The liquid chromatogram is used for tracking the complete disappearance of the reactants, and the temperature is reduced to 90-95 ℃. Filtering and recovering the alkylbenzene mother liquor. Washing the filter cake with a small amount of ethanol until the filtrate is colorless, and recovering the washing liquid. The filter cake was washed with water until the pH was neutral and transferred to the next step for treatment.
Adding 100 ml of butanol solution into the filter cake, fully stirring for 2 hours, then heating to reflux, keeping the reflux for 3 hours, cooling to 50 ℃, performing heat filtration, and recovering mother liquor. Washed with a small amount of water and dried to obtain about 6.1 g of dry powder. Appearance: bright red powder, yield 86.5%.
Example 2
Except that cuprous chloride was used as a catalyst in place of cuprous iodide in the above preparation process, the procedure of example 1 was repeated to obtain about 5.9 g of a dry powder, as in example 1. Appearance: bright red powder, yield 83.7%.
Example 3
The difference from example 1 is that o-dichlorobenzene is used as a solvent instead of alkylbenzene, 6.8 parts of 6-bromo-N-methyl-anthrapyridone, 1.87 parts of benzoguanamine and 0.42 part of cuprous iodide as a catalyst are added into a 250mL four-neck flask, 80 mL of o-dichlorobenzene solution is added, the temperature is raised to 170 ℃, the reaction is kept at a constant temperature, 2.1 parts of sodium bicarbonate as an acid binding agent are added in portions during the reaction, the pH value of the reaction is adjusted, the reaction is carried out for 12 hours, and the liquid chromatography shows that the consumption of raw materials in the system is finished and the reaction is finished. Cooling to 90-95 deg.C, filtering, washing with o-dichlorobenzene until the filtrate is colorless, washing with alcohol and water to neutrality to obtain wet filter cake, and recovering the filtrate.
And adding 100 ml of butanol solution into the filter cake, fully stirring for 2 hours, heating to reflux, keeping the temperature and refluxing for 3 hours, cooling, filtering, washing with water and drying. About 6.12 grams of dry powder was obtained. Appearance: the red yield was 86.8%.
The dry powder samples obtained in the above examples are respectively observed under a 400-fold optical microscope in a transmission manner, and the samples are fine rod-shaped crystals, fine particles, uniform in size distribution, and free of obvious large aggregates (see fig. 1), so that the coloring agent has good color performance and easy dispersibility when being applied to resin for coloring. Meanwhile, the sample is observed to have obvious rod-like crystal morphology through scanning of an electron microscope (see figure 2).
The sample obtained above was then subjected to further XRD analysis (see fig. 3), and the prepared dry powder sample compound had distinct crystallinity and crystallinity, with organic pigment characteristics.
Therefore, the obtained colorant has a complete and regular crystal morphology and has the characteristics of an organic pigment. The compound has relatively perfect crystal structure and crystallinity, so that the compound has good temperature resistance, solvent resistance and chemical resistance, and shows good color effect.
Example 4
2, 4-diamino-6-benzene-1, 3, 5-triazine was replaced with 2.01 parts of 2, 4-diamino-6-methylbenzene-1, 3, 5-triazine by the same preparation method as in example 1 above to give about 5.96 g of a dry powder. Appearance: dark red, yield 82.9%.
Example 5
2, 4-diamino-6-benzene-1, 3, 5-triazine was replaced with 2.21 parts of 2, 4-diamino-6-chlorobenzene-1, 3, 5-triazine by the same procedure as in example 1 to give about 6.15 g of a dry powder. Appearance: dark red powder, yield 83.2%.
Meanwhile, other compounds for obtaining the R ═ alkyl, alkoxy or halogen provided by the present invention can be prepared by replacing the raw materials according to the above-mentioned preparation method, and the above-mentioned advantageous characteristics are also obtained in addition to the shift of the color phase.
Application examples
The following examples illustrate in detail the application properties and the application effects of the colorants according to the invention, taking the sample obtained in example 1 above as an example, while other compounds defined according to the invention also have corresponding effect characteristics.
Example 6: color characterization test
The sample obtained in example 1 was uniformly mixed with polyester PET powder in an amount of 1 wt%, injection-molded at 280 ℃ to prepare a PET injection-molded sheet, and color measurement was carried out using an electronic colorimeter under a D65 light source with a Lab system, wherein the color characteristics of the sample are as shown in Table 1:
table 1: color value of PET injection molded sheet of sample
Table 1 shows that the compound of the present invention is brilliant yellow red, has excellent vividness, and can be used as a coloring agent.
Example 7: easy dispersibility test
The colorant dry powder of example 1 without pre-dispersion and pulverization was taken and homogenized with No. 6 varnish on a flat mill. Grinding is carried out under the condition of not adding weights, and the change of the grinding fineness of the colorant is tracked and detected by a scraper fineness meter.
Table 2: easy dispersibility of samples
Generally, organic pigments with perfect crystallization are easy to aggregate into particles during drying to form hard particles, are difficult to disperse into application media, and have to be subjected to pre-dispersion treatment and efficient pulverization treatment, and are applied after being sieved through a certain number of sieves, such as 100 meshes, 300 meshes and the like. When the pressure is detected by using a plain grinding machine, a certain pressure is used, and the pressure of the plain grinding machine with a weight is 47 kilograms. The samples used in the application example are directly detected by a flat grinder without any pre-dispersion treatment and crushing treatment. And the weight of the flat grinding instrument is removed during detection. The test results in Table 2 show that the colorant of the present invention can be completely dispersed under a small grinding condition without pre-dispersion and pulverization treatment, and the colorant of the present invention has a good easy dispersibility.
Example 8: solvent resistance detection
The sample of example 1 of the present invention was tested for fastness properties according to water resistance, solvent resistance, acid and alkali resistance of GB/T5211.5-2008 "pigment resistance test method". The results are shown in Table 3:
TABLE 3: partial fastness Properties of samples
The compound meets the requirements of solvent resistance and chemical resistance of a high-performance colorant, and can avoid the mobility problem caused by solubility in resin application.
Example 9: heat resistance test
The colorant obtained in example 1 was mixed with a PET resin in an amount of 1 wt% to obtain a mixture, which was subjected to injection molding at 300 ℃. The retention time is 15 seconds and 5 minutes respectively, and an injection molding sheet is prepared for color difference detection. And simultaneously, performing injection molding under the same conditions by using C.I. pigment yellow 147 which is recognized in the field and can meet the coloring temperature resistance requirement of the PET fiber stock solution, and contrasting the discoloration condition. The heat resistance of the sample of example 1 in the PET resin was judged by DE comparison using an electronic colorimeter under a Lab system under a D65 light source. The results are shown in Table 4
Table 4: heat resistance in sample PET resin
The test result shows that the colorant provided by the invention has good temperature resistance, and has better temperature resistance compared with the high-temperature-resistance C.I. pigment yellow 147 commonly used in the industry. Can meet the high-temperature processing coloring requirement of resins such as PET and the like, and simultaneously avoids color migration caused by poor temperature resistance.
Example 10: migration resistance test
The method for measuring the migration resistance comprises the following steps: the sample obtained in example 1 was uniformly mixed with a polyester PET powder in an amount of 2 wt%, injection-molded at 275 ℃ to prepare a PET injection-molded sheet, a (3.2X 2.0) cm colored PET sheet was placed on a white PET knitted fabric, the sheet was placed in a thermal cycle oven having an internal temperature of 180 ℃ for 3 minutes under a pressure of 7MPa, and then the colored PET sheet was removed to observe the degree of staining on the white PET knitted fabric (the degree of DE value was measured by an electronic colorimeter using a Lab system under a D65 light source), and the sheet was evaluated according to ISO 105-A03. Grade 5 indicates no migration, grade 1 indicates severe migration, and the results of the migration resistance test are shown in table 5:
table 5: sample migration resistance test
The test result shows that the colorant has good migration resistance, and is judged to be 4-5 grade according to ISO105-A03 detection standard.
Claims (10)
1. A red organic colorant for use in resin coloration, characterized by: the colorant is a compound shown in a general formula I,
in the formula:
r is selected from hydrogen and C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a).
2. A red organic colorant for resin coloration according to claim 1, wherein: in the general formula I, R is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, chlorine or bromine.
3. A red organic colorant for resin coloration according to claim 2, wherein: in the general formula I, R is selected from hydrogen, methyl or chlorine.
4. A method for preparing the red organic colorant for coloring resin according to claim 1, wherein:
wherein: x is selected from Cl and Br;
r is selected from-H, C1-C4Alkyl of (C)1-C4Alkoxy or halogen of (a);
the compound of the general formula I is obtained by mixing 6-X-N-methyl-anthrapyridone and 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine and subjecting the mixture to Ullmann condensation reaction in a high boiling point organic solvent in the presence of a catalyst and an acid-binding agent.
5. The process for preparing a red organic colorant for coloring resins according to claim 4, wherein: mixing the 6-X-N-methyl-anthrapyridone with 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine, and carrying out Ullmann condensation reaction for 10-12h at 160-180 ℃ in a high-boiling-point organic solvent in the presence of a catalyst and an acid-binding agent to obtain a compound shown in a general formula I; wherein the mol ratio of the 6-X-N-methyl-anthrapyridone to the 2, 4-diamino-6-substituted phenyl-1, 3, 5-triazine is 2:1, the weight ratio of the high-boiling-point organic solvent to 6-X-N-methyl-anthrapyridone is 10-13: 1, the molar ratio of the acid-binding agent to 6-X-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to 6-X-N-methyl-anthrapyridone is 1: 14-16.
6. A method for preparing the red organic colorant for coloring resin according to claim 1, wherein: reaction formula is
The compound of the general formula I is obtained by carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high boiling point organic solvent in the presence of an acid binding agent and a catalyst.
7. The process for preparing a red organic colorant for resin coloration according to claim 6, wherein: carrying out Ullmann condensation reaction on 6-amino-N-methyl-anthrapyridone and 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine in a high-boiling-point organic solvent at the temperature of 160-170 ℃ in the presence of an acid binding agent and a catalyst for 10-12h to obtain a compound shown in a general formula I; wherein the mol ratio of the 6-amino-N-methyl-anthrapyridone to the 2, 4-dichloro-6-substituted phenyl-1, 3, 5-triazine is 2:1, and the weight ratio of the high boiling point organic solvent to the 6-amino-N-methyl-anthrapyridone is 11-13: 1, the molar ratio of the acid-binding agent to the 6-amino-N-methyl-anthrapyridone is 1: 1, the weight ratio of the catalyst to the 6-amino-N-methyl-anthrapyridone is 1: 14-16.
8. The process for preparing a red organic colorant for resin coloration according to claim 4, 5, 6 or 7, wherein: the catalyst is selected from copper powder, cuprous chloride, cuprous iodide, copper acetate or copper sulfate; the acid-binding agent is alkali metal carbonate or alkali metal bicarbonate; the high boiling point organic solvent is alkylbenzene, dichlorobenzene, nitrobenzene, dimethyl sulfoxide or N-methyl pyrrolidone.
9. The process for preparing a red organic colorant for resin coloration according to claim 4, 5, 6 or 7, wherein: after Ullmann condensation reaction, the product is subjected to heat treatment by a polar organic solvent to obtain the red powdery compound with the general formula I and the soft structure.
10. Use of a red organic colorant according to claim 1, wherein: the compound of the general formula I is applied to being used as a coloring agent for resin.
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