Method for synthesizing aromatic diamide nucleating agent without solvent

Abstract

The invention relates to the related technical field of synthesis of aromatic diamide nucleating agents, and particularly provides a method for synthesizing an aromatic diamide nucleating agent without a solvent. The method comprises the following steps: firstly, uniformly mixing a compound shown as a formula (I) and an acyl halide reagent, and then adding an organic base catalyst containing nitrogen atoms; then, carrying out acylating chlorination reaction at 50-100 DEG C to obtain a compound as shown in a formula (II); the compound shown in the formula (II) and an organic primary amine compound are ground at the temperature of 20-100 DEG C to be subjected to amidation reaction, and the aromatic diamide nucleating agent shown in the formula (III) is obtained. According to the present invention, the aromatic diamide nucleating agent is synthesized under the solvent-free condition, such that the use of the large amount of the solvent is avoided, the final product aromatic diamide nucleating agent has characteristics of high yield and high purity, the synthesis process flow is simplified, and the method is suitable for industrial amplification and production; and the method plays a positive role in practical application of the aromatic diamide nucleating agent.

Description

Technical Field

[0001] The present application relates to the technical field related to the synthesis of aromatic diamide nucleating agents, and specifically provides a method for synthesizing aromatic diamide nucleating agents without solvent. Background Art

[0002] Nucleating agents are new functional additives suitable for incompletely crystalline plastics such as polyethylene and polypropylene. By modifying the resin's crystallization behavior, accelerating the crystallization rate, increasing the crystal density, and miniaturizing the grain size, they shorten the molding cycle and improve physical and mechanical properties such as product transparency, surface gloss, tensile strength, rigidity, heat distortion temperature, impact resistance, and creep resistance. Polypropylene, due to its low specific gravity, high tensile yield strength, flexural modulus, and hardness, and excellent resistance to environmental stress cracking, coupled with its abundant raw material resources and low price, is well-suited for injection molding plastic products. Polypropylene is a crystalline polymer with large spherulites within it, resulting in very low impact strength and severe post-shrinkage in finished products, which limits its use in injection molding. By adding nucleating agents to generate a microcrystalline structure of polypropylene, the resin is modified to achieve high performance. When nucleating agents are added to polypropylene, they effectively promote and accelerate the crystallization process, imparting a microcrystalline structure to the molecules. This not only improves the product's impact strength and yield strength, but also enhances its appearance, shortens the injection cycle, and increases productivity. With the development of new polypropylene products and grades, nucleating agents will be more widely used in various areas of new polypropylene product development. Nucleating agents are primarily classified into two categories: α-nucleating agents and β-nucleating agents, depending on their nucleation mechanism. In recent nucleating agent research and development, aromatic diamide nucleating agents are considered to offer a very high nucleation efficiency.

[0003] At present, the methods for synthesizing aromatic diamide nucleating agents are mainly as follows: using aromatic dicarboxylic acid and organic amine as raw materials, triphenylphosphine and pyridine as catalysts, N -Methyl pyrrolidone is used as solvent, the reaction is carried out at 100 ° C, and then is treated with isopropanol-water to obtain the product. This process has the following disadvantages: (1) the cost of the catalyst triphenylphosphine is high, the amount used is large, and the generated triphenylphosphine oxide is difficult to separate and recycle; (2) the raw material aromatic dicarboxylic acid has poor solubility, so a large amount of expensive N -Methyl pyrrolidone is used as a solvent, which is mixed with isopropanol-water during post-treatment and is difficult to recycle; (3) a large amount of isopropanol-water is used in the post-reaction treatment, which is difficult to separate and recycle; (4) the reaction operation is complicated and the purity of the product cannot be guaranteed.

[0004] In view of the poor solubility of raw materials, intermediates and products in solvents in the preparation process of nucleating agents, the existing process often uses a large amount of special solvent to dissolve the materials, and the use amount of reaction solvents and post-processing solvents often reaches dozens to more than one hundred times of the amount of raw materials. After the reaction is completed, long and complicated post-processing operations are required to remove the solvents, and then the product can be separated and purified to achieve the desired purity. Due to the use of a large amount of solvent in the synthesis process of the nucleating agent, the volume of reaction materials is large, the post-processing is complicated, the post-processing time is long, and other disadvantages, which leads to the need to use more and larger reaction equipment for industrial scale production, the operation time is long, the energy consumption is high, the requirement for solvent recovery equipment is high, and it also has a certain impact on the production environment. Due to the large cost of solvents, equipment, labor and environmental protection, the product cost is high, the yield is limited, which affects the practical application of the nucleating agent. SUMMARY

[0005] In view of this, the present application provides a method for synthesizing aromatic diamide nucleating agent without solvent, which comprises the following steps:

[0006] Step S1, first mix the compound of formula (I) and the acyl halide reagent uniformly, then add the nitrogen atom-containing organic base catalyst; then, an acyl chloride reaction occurs at 50-100°C to obtain a compound of formula (II); wherein the molar ratio of the compound of formula (I), the acyl halide reagent and the organic base catalyst is 1:(2.0-20.0):(0.05-2.0); the organic base catalyst includes a pyridine organic base catalyst and a non-pyridine organic base catalyst with a molar ratio of 1:(0.1-0.3); Step S2, the compound of formula (II) and the organic primary amine compound are ground at 20-100°C to cause an amidation reaction to obtain an aromatic diamide nucleating agent as shown in formula (III); wherein R1 is independently selected from unsubstituted or substituted C5-C10 alkyl or unsubstituted or substituted C5-C10 aromatic group; the substituent group in the substituted C5-C10 alkyl is selected from C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl or halogen; the substituent group in the substituted C5-C10 aromatic group is selected from C1-C3 alkyl, C1-C3 alkoxy or halogen; the molar ratio of the compound of formula (II) and the organic primary amine compound is 1:(4.0-10.0).

[0007] wherein the structure of the organic primary amine compound is wherein R1 is defined as above.

[0008] In some optional embodiments, the molar ratio of the compound of formula (I), the acyl halide reagent and the organic base catalyst is 1:(5.0-15.0):(0.1-0.5). Wherein, the molar ratio of the compound of formula (I) and the acyl halide reagent can be 1:5.0, 1:5.5, 1:6.0, 1:6.5, 1:7.0, 1:7.1, 1:7.2, 1:7.3, 1:7.4, 1:7.5, 1:7.6, 1:7.7, 1:7.8, 1:7.9, 1:8.0, 1:8.1, 1:8.2, 1:8.3, 1:8.4, 1:8.5, 1:8.6, 1:8.7, 1:8.8, 1:8.9, 1:9.0, 1:9.1 , 1:9.2, 1:9.3, 1:9.4, 1:9.5, 1:9.6, 1:9.7, 1:9.8, 1:9.9, 1:10.0, 1:10.1, 1:10.2, 1:10.3, 1:10.4, 1:10.5, 1:10.6, 1:10.7, 1:10.8, 1:10.9, 1:11.0, 1:11.5, 1:12.0, 1:12.5, 1:13.0, 1:13.5, 1:14.0, 1:14.5 or 1:15.0, etc. The molar ratio of the compound of formula (I) to the organic base catalyst can be 1:0.1, 1:0.2, 1:0.3, 1:0.4 or 1:0.5, etc.

[0009] In some optional embodiments, the molar ratio of the compound of formula (II) to the organic primary amine compound is 1:(4.0-5.0). The molar ratio of the compound of formula (II) to the organic primary amine compound can be 1:4.0, 1:4.1, 1:4.2, 1:4.3, 1:4.4, 1:4.5, 1:4.6, 1:4.7, 1:4.8, 1:4.9 or 1:5.0, etc.

[0010] In some optional embodiments, the organic base catalyst includes a pyridine organic base catalyst and a non-pyridine organic base catalyst in a molar ratio of 1:(0.15-0.25); for example, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, 1:0.2, 1:0.21, 1:0.22, 1:0.23, 1:0.23 or 1:0.25, etc.

[0011] In some alternative embodiments, the pyridine-based organic base catalyst comprises at least one of pyridine (abbreviated as Py, CAS number 110-86-1), 2,3-dimethylpyridine (CAS number 1122-58-3), 2,3-dimethylpyridine (CAS number 583-61-9), 2,4-dimethylpyridine (CAS number 108-47-4), 2,5-dimethylpyridine (CAS number 589-93-5), 2,6-dimethylpyridine (CAS number 108-48-5), 3,4-dimethylpyridine (CAS number 583-58-4), or 3,5-dimethylpyridine (CAS number 591-22-0).

[0012] In some particular embodiments, the pyridine-based organic base catalyst is selected from pyridine.

[0013] In some alternative embodiments, the non-pyridine-based organic base catalyst comprises at least one of triethylamine (CAS number 121-44-8), tripropylamine (CAS number 102-69-2), N,N-dimethylformamide (CAS number 68-12-2), or N,N-dimethylacetamide (CAS number 127-19-5).

[0014] In some alternative embodiments, the non-pyridine-based organic base catalyst comprises triethylamine and N,N-dimethylacetamide. In other alternative embodiments, the non-pyridine-based organic base catalyst comprises triethylamine and N,N-dimethylacetamide in a molar ratio of 1 : (0.3-0.5); for example, 1 :0.3, 1 :0.31, 1 :0.32, 1 :0.33, 1 :0.34, 1 :0.35, 1 :0.36, 1 :0.37, 1 :0.38, 1 :0.39, 1 :0.4, 1 :0.41, 1 :0.42, 1 :0.43, 1 :0.44, 1 :0.45, 1 :0.46, 1 :0.47, 1 :0.48, 1 :0.49, or 1 :0.5, etc. In some particular embodiments, the non-pyridine-based organic base catalyst comprises triethylamine and N,N-dimethylacetamide in a molar ratio of 1 :0.4.

[0015] In some alternative embodiments, the compound of formula (I) is selected from 1,5- naphthalene dicarboxylic acid (CAS number 7315-96-0), 1,6-naphthalene dicarboxylic acid, 1,7-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid (CAS number 518-05-8), 2,6-naphthalene dicarboxylic acid (CAS number 1141-38-4), 2,7-naphthalene dicarboxylic acid, at least one of 1,5-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, or 2,7-naphthalene dicarboxylic acid.

[0016] In other optional embodiments, the compound of Formula (I) comprises at least one of 1,5-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, or 2,7-naphthalene dicarboxylic acid. In some specific embodiments, the compound of Formula (I) is selected from 1,5-naphthalene dicarboxylic acid. In some specific embodiments, the compound of Formula (I) is selected from 2,6-naphthalene dicarboxylic acid. In some specific embodiments, the compound of Formula (I) is selected from 2,7-naphthalene dicarboxylic acid.

[0017] In some optional embodiments, the acyl halogenating reagent comprises at least one of a halogenated sulfoxide (e.g., sulfurous acid chloride, etc.) or a phosphorus trihalide (e.g., phosphorus trichloride). In other optional embodiments, the acyl halogenating reagent comprises at least one of dichlorosulfoxide or dibromosulfoxide. In some specific embodiments, the acyl halogenating reagent is selected from dichlorosulfoxide.

[0018] In some optional embodiments, R1is independently selected from .

[0019] In other optional embodiments, R1is independently selected from , or . In some specific embodiments, R1is selected from . In some specific embodiments, R1is selected from . In some specific embodiments, R1is selected from .

[0020] In some optional embodiments, the organic primary amine compounds include cyclopentylamine (CAS No. 1003-03-8), 1-methylcyclopentylamine (CAS No. 40571-45-7), 2-methylcyclopentylamine (CAS No. 41223-14-7), 3-methylcyclopentylamine (CAS No. 52430-83-8), 2,5-dimethylcyclopentylamine (CAS No. 80874-82-4), 1-ethylcyclopentylamine (CAS No. 67404-87-9), 2-ethylcyclopentylamine (CAS No. 900641-94-3), 3-ethylcyclopentylamine (CAS No. 1267496-90-1), 2-fluorocyclopentylamine (C 2-Methylcyclohexylamine (CAS No. 7003-32-9), 3-Methylcyclohexylamine (CAS No. 6850-35-7), 4-Methylcyclohexylamine (CAS No. 6321-23-9), 1-Fluorocyclohexylamine (CAS No. 94558-85 -7), 2-fluorocyclohexylamine (CAS No. 1039741-13-3), 3-fluorocyclohexylamine (CAS No. 1273566-51-0), 4-fluorocyclohexylamine (CAS No. 1314924-99-6), 3-chlorocyclohexylamine (CAS No. 1045859-81-1), 4-chlorocyclohexylamine (CAS No. 59477-35-9), 2-bromocyclohexylamine (CAS No. 861776-21-8), 3-bromocyclohexylamine (CAS No. 859936-66-6), 4-bromocyclohexylamine (CAS No. 326495-99-2), 4-iodocyclohexylamine (CAS No. 1354087-63-0) , 4,4-difluorocyclohexylamine (CAS No. 458566-84-2), 1-methyl-4-bromocyclohexylamine (CAS No. 2840085-65-4), cycloheptylamine (CAS No. 5452-35-7), 4-methylcycloheptane-1-amine (CAS No. 855590-29-3), 4-isopropylcycloheptane-1-amine (CAS No. 1495590-92-5), 2-fluorocycloheptane-1-amine (CAS No. 1427378-70-8), 3-fluorocycloheptane-1-amine (CAS No. 1461715-22-9), 4-fluorocycloheptane-1-amine (CAS No. 1461709-12-5), 4,4-Difluorocycloheptane-1-amine (CAS No. 1461708-43-9), cyclooctylamine (CAS No. 5452-37-9), aniline (CAS No. 62-53-3), 2-methylaniline (CAS No. 95-53-4), 3-methylaniline (CAS No. 108-44-1), 4-methylaniline (CAS No. 106-49-0), 2-fluoroaniline (CAS No. 348-54-9), 3-fluoroaniline (CAS No. 372-19-0), 4-fluoroaniline (CAS No. At least one of the following: 2-chloroaniline (CAS No. 371-40-4), 2-chloroaniline (CAS No. 95-51-2), 2-bromoaniline (CAS No. 615-36-1), 3-bromoaniline (CAS No. 591-19-5), 2-iodoaniline (CAS No. 615-43-0), 2-bromo-3-chloroaniline (CAS No. 96558-73-5), 4-tert-butyl-3-chloroaniline (CAS No. 52756-36-2) or 2,4-dibromo-3-chloroaniline (CAS No. 80026-15-9).

[0021] In other optional embodiments, the organic primary amine compound includes at least one of cyclopentylamine, cyclohexylamine, or aniline. In some specific embodiments, the organic primary amine compound is selected from cyclopentylamine. In some specific embodiments, the organic primary amine compound is selected from cyclohexylamine. In some specific embodiments, the organic primary amine compound is selected from aniline.

[0022] In some optional embodiments, the aromatic diamide nucleating agent includes N,N'-dicyclopentyl-1,5-naphthalene dicarboxamide ( )、N,N'-dicyclohexyl-1,5-naphthalene dicarboxamide( )、N,N'-diphenyl-1,5-naphthalene dicarboxamide( )、N,N'-dicyclopentyl-2,6-naphthalene dicarboxamide( )、N,N'-dicyclohexyl-2,6-naphthalene dicarboxamide( , CAS No. 153250-52-3) or N,N'-diphenyl-2,6-naphthalene dicarboxamide ( In some embodiments, the aromatic diamide nucleating agent is selected from N,N'-dicyclohexyl-2,6-naphthalene dicarboxamide.

[0023] In some optional embodiments, in step S1, the reaction temperature of the acyl chloride reaction is 50-80°C; for example, 50°C, 55°C, 60°C, 65°C, 70°C, 75°C or 80°C.

[0024] In some optional embodiments, in step S1, the reaction time of the chlorination reaction is 2 to 10 hours; for example, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, 9 hours, 9.5 hours or 10 hours, etc.

[0025] In some optional embodiments, in step S2, the reaction temperature of the amidation reaction is 20-70°C; for example, 20°C, 25°C, 30°C, 35°C, 40°C, 45°C, 50°C, 55°C, 60°C, 65°C or 70°C, etc.

[0026] In some optional embodiments, in step S2, the reaction time of the amidation reaction is 5 to 20 hours, for example, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, 9 hours, 9.5 hours, 10 hours, 10.5 hours, 11 hours, 11.5 hours, 12 hours, 12.5 hours, 13 hours, 13.5 hours, 14 hours, 14.5 hours, 15 hours, 15.5 hours, 16 hours, 16.5 hours, 17 hours, 17.5 hours, 18 hours, 18.5 hours, 19 hours, 19.5 hours or 20 hours, etc.

[0027] This application has the following beneficial effects: First, the present invention synthesizes aromatic diamide nucleating agents under solvent-free conditions, avoiding the use of large amounts of solvent. This not only allows the intermediate product, compound (II), to be directly used in the next step of preparation without separation and purification, but also simplifies the post-processing of the final aromatic diamide nucleating agent. Furthermore, the final aromatic diamide nucleating agent has a high yield and high purity. Thus, the synthetic process is simplified, making it suitable for industrial scale-up and production, and has a positive impact on the practical application of aromatic diamide nucleating agents.

[0028] Second, the method of the present application can effectively reduce the size of the equipment, reduce the number of equipment, and thus reduce the preparation cost.

[0029] Third, the process operation is green and environmentally friendly, does not use organic solvents, and is environmentally friendly. DETAILED DESCRIPTION

[0030] This application discloses a method for solvent-free synthesis of aromatic diamide nucleating agents. Those skilled in the art can refer to the content of this application and appropriately improve the process parameters to achieve the desired effect. It should be noted that all similar substitutions and modifications are obvious to those skilled in the art and are considered to be included in this application. The methods and applications of this application have been described through preferred embodiments. It is obvious that relevant personnel can modify or appropriately change and combine the methods and applications described herein without departing from the content, spirit and scope of this application to implement and apply the technology of this application.

[0031] In order to make the purpose, technical solutions and advantages of this application clearer, the implementation scheme of this application will be further described in detail with reference to examples below.

[0032] Examples of aromatic diamide nucleating agents: In this embodiment, the aromatic diamide nucleating agent is N,N'-dicyclohexyl terephthalamide as an example. Specifically, the synthesis route of N,N'-dicyclohexyl terephthalamide is as follows:

[0033] Step S1, synthesis of terephthaloyl chloride: Terephthalic acid and thionyl chloride were added to a 250 mL reaction flask at room temperature and stirred evenly. 1.0 g of an organic base catalyst was added dropwise. The temperature was raised to 65°C and stirred at 65°C for 4 hours. The white solid was evenly dispersed in the reaction mixture. The excess thionyl chloride was recovered by vacuum distillation on a rotary evaporator at 50-65°C / 20 mmHg (a fraction was distilled out at 36°C) to obtain a white solid.

[0034] Step S2, synthesis of N,N'-dicyclohexylterephthalamide: At room temperature, the terephthaloyl chloride and cyclohexylamine obtained in step S1 were added sequentially to a grinder (wherein the molar ratio of terephthaloyl chloride to cyclohexylamine was 1:5.0). The grinder was started and ground at room temperature for 6 hours to complete the reaction. The reaction mixture in the grinder was transferred to a beaker, 50 mL of water was added, stirred and slurried, filtered, and washed with water 4 times (50 mL each time), filtered; the filter cake was heated at 70 The product was dried under forced air at 4 °C for 4 hours and crushed to obtain N,N'-dicyclohexylterephthalamide in the form of white powder.

[0035] Detection of the purity of N,N'-dicyclohexylterephthalamide: High Performance Liquid Chromatography (HPLC).

[0036] Table 1. Reaction conditions in step S1 for the synthesis of N,N'-dicyclohexylterephthalamide:

[0037] Unless otherwise specified, the molecular weight of "terephthalic acid" used in this application is 203.02; the molecular weight of "dichlorothionyl" used in this application is 118.97; the molecular weight of "pyridine" used in this application is 79.10; the molecular weight of "triethylamine" used in this application is 101.19; the molecular weight of "N,N-dimethylacetamide" used in this application is 87.12; the molecular weight of "terephthaloyl chloride" used in this application is 203.02; and the molecular weight of "N,N'-dicyclohexylterephthalamide" used in this application is 328.46.

[0038] As can be seen from Table 1, the present application synthesizes aromatic diamide nucleating agents under solvent-free conditions, avoiding the use of a large amount of solvent. This not only allows the intermediate product compound (II) to be directly used in the next step of preparation without separation and purification, but also simplifies the post-processing of the final aromatic diamide nucleating agent, and the final aromatic diamide nucleating agent has a high yield and high purity. Therefore, the synthetic process flow is simplified, suitable for industrial scale-up and production, and has a positive effect on the practical application of aromatic diamide nucleating agents.

[0039] Comparison of Experiments 1-2 and 5 shows that the purity of the aromatic diamide nucleating agent is significantly improved by using a combination of a pyridine organic base and a non-pyridine organic base as the organic base catalyst in this application. Furthermore, comparison of Experiments 1 and 3-4 shows that the final yield of the aromatic diamide nucleating agent is slightly improved by using a combination of triethylamine and N,N-dimethylacetamide as the non-pyridine organic base.

[0040] The above is a detailed introduction to the solvent-free synthesis method of aromatic diamide nucleating agents provided by this application. This article uses specific examples to illustrate the principles and implementation methods of this application. The description of the above examples is only used to help understand the method and core concept of this application. It should be pointed out that for those skilled in the art, without departing from the principles of this application, various improvements and modifications can be made to this application, and these improvements and modifications also fall within the scope of protection of the claims of this application.

Claims

1. A method for solvent-free synthesis of aromatic diamide nucleating agents, characterized in that: The method comprises the following steps: ； Step S1, first uniformly mixing the compound of formula (I) and the acyl halide reagent, then adding a nitrogen-containing organic base catalyst; then, performing an acyl chlorination reaction at 50-100° C. to obtain a compound of formula (II); wherein the molar ratio of the compound of formula (I), the acyl halide reagent, and the organic base catalyst is 1:(2.0-20.0):(0.05-2.0); the organic base catalyst comprises a pyridine organic base catalyst and a non-pyridine organic base catalyst in a molar ratio of 1:(0.1-0.3); Step S2, grinding the compound of formula (II) and the organic primary amine compound at 20-100° C. to cause an amidation reaction to obtain an aromatic diamide nucleating agent as shown in formula (III); wherein R1 is independently selected from an unsubstituted or substituted C5-C10 alkyl group or an unsubstituted or substituted C5-C10 aromatic group; the substituent in the substituted C5-C10 alkyl group is selected from a C1-C3 alkoxy group, a C2-C3 alkenyl group, a C2-C3 alkynyl group or a halogen; the substituent in the substituted C5-C10 aromatic group is selected from a C1-C3 alkyl group, a C1-C3 alkoxy group or a halogen; and the molar ratio of the compound of formula (II) to the organic primary amine compound is 1:(4.0-10.0).

2. The method according to claim 1, characterized in that The molar ratio of the compound of formula (I), the acyl halide reagent and the organic base catalyst is 1:(5.0-15.0):(0.1-0.5).

3. The method according to claim 1, characterized in that The molar ratio of the compound of formula (II) to the organic primary amine compound is 1:(4.0-5.0).

4. The method according to any one of claims 1 to 3, characterized in that The organic base catalyst includes a pyridine organic base catalyst and a non-pyridine organic base catalyst in a molar ratio of 1:(0.15-0.25).

5. The method according to claim 4, characterized in that The pyridine organic base catalyst includes at least one of pyridine, 4-dimethylaminopyridine, 2,3-lutidine, 2,4-lutidine, 2,5-lutidine, 2,6-lutidine, 3,4-lutidine or 3,5-lutidine.

6. The method according to claim 5, characterized in that The pyridine organic base catalyst is selected from pyridine.

7. The method according to claim 4, characterized in that The non-pyridine organic base catalyst includes at least one of triethylamine, tripropylamine, N,N-dimethylformamide or N,N-dimethylacetamide.

8. The method according to claim 7, characterized in that The non-pyridine organic base catalyst comprises triethylamine and N,N-dimethylacetamide in a molar ratio of 1:(0.3-0.5).

9. The method according to claim 1, characterized in that The compound of formula (I) includes at least one of 1,5-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid or 2,7-naphthalene dicarboxylic acid; and / or, the acyl halide reagent comprises at least one of thionyl chloride or thionyl bromide; and / or, R1 independently comprises ； And / or, the organic primary amine compound includes cyclopentylamine, 1-methylcyclopentylamine, 2-methylcyclopentylamine, 3-methylcyclopentylamine, 2,5-dimethylcyclopentylamine, 1-ethylcyclopentylamine, 2-ethylcyclopentylamine, 3-ethylcyclopentylamine, 2-fluorocyclopentylamine, 3-fluorocyclopentylamine, 1-vinylcyclopentylamine, 1-ethynylcyclopentylamine, cyclohexylamine, 1-methylcyclohexylamine, 2-methylcyclohexylamine, 3-methylcyclohexylamine, 4-methylcyclohexylamine, 1-fluorocyclohexylamine, 2-fluorocyclohexylamine, 3-fluorocyclohexylamine, 4-fluorocyclohexylamine, 3-chlorocyclohexylamine, 4-chlorocyclohexylamine, 2-bromocyclohexylamine, 3-bromocyclohexylamine, 4-bromocyclohexylamine, 4- At least one of iodocyclohexylamine, 4,4-difluorocyclohexylamine, 1-methyl-4-bromocyclohexylamine, cycloheptylamine, 4-methylcycloheptane-1-amine, 4-isopropylcycloheptane-1-amine, 2-fluorocycloheptane-1-amine, 3-fluorocycloheptane-1-amine, 4-fluorocycloheptane-1-amine, 4,4-difluorocycloheptane-1-amine, cyclooctylamine, aniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 2-fluoroaniline, 3-fluoroaniline, 4-fluoroaniline, 2-chloroaniline, 2-bromoaniline, 3-bromoaniline, 2-iodoaniline, 2-bromo-3-chloroaniline, 4-tert-butyl-3-chloroaniline, or 2,4-dibromo-3-chloroaniline; And / or, the aromatic diamide nucleating agent includes at least one of N,N'-dicyclopentyl-1,5-naphthalene dicarboxamide, N,N'-dicyclohexyl-1,5-naphthalene dicarboxamide, N,N'-diphenyl-1,5-naphthalene dicarboxamide, N,N'-dicyclopentyl-2,6-naphthalene dicarboxamide, N,N'-dicyclohexyl-2,6-naphthalene dicarboxamide or N,N'-diphenyl-2,6-naphthalene dicarboxamide.

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