A highly wear-resistant TPR thermoplastic elastomer and its preparation method

Abstract

This invention relates to the field of rubber elastomer technology, and discloses a high-wear-resistant TPR thermoplastic elastomer and its preparation method. The high-wear-resistant TPR thermoplastic elastomer comprises 100 parts by weight of SBS styrene-butadiene styrene copolymer, 30-60 parts by weight of nylon 6, 2-10 parts by weight of hyperbranched triazine polyarylamide, and 0.3-1.6 parts by weight of maleic anhydride-grafted SBS, etc. The hyperbranched triazine polyarylamide has good compatibility with SBS styrene-butadiene styrene copolymer and nylon 6, and is uniformly dispersed in the SBS styrene-butadiene styrene copolymer and nylon 6 thermoplastic elastomer matrix, improving the material's tensile strength, Shore A hardness, wear resistance, and other properties.

Description

Technical Field

[0001] This invention relates to the field of rubber elastomer technology, specifically to a highly wear-resistant TPR thermoplastic elastomer and its preparation method. Background Technology

[0002] Thermoplastic elastomers (TPE), also known as synthetic rubber or artificial rubber, have become a new type of material replacing traditional rubber due to their advantages such as being environmentally friendly and non-toxic, highly elastic, having good aging resistance, and being easy to process. They have wide applications in industrial production and daily life. SBS (styrene-butadiene-styrene copolymer) is a copolymer formed by polymerizing styrene and butadiene monomers. It has good oil resistance, good heat resistance, and strong adhesion, and is widely used.

[0003] Combining SBS styrene-butadiene styrene copolymer with nylon, polypropylene, polyvinyl chloride, etc., yields composite materials with excellent properties. For example, patent CN101629013B discloses a plastic alloy of PPE and PA66 with high impact toughness and its preparation method. Using polyphenylene ether resin (PPE), nylon 66, thermoplastic elastomers, and SBS-type compatibilizers as raw materials, the resulting plastic alloy exhibits good impact toughness. Hyperbranched polymers, such as hyperbranched polyarylamides, hyperbranched polyesters, and hyperbranched polyurethanes, possess highly branched three-dimensional molecular chain structures, unique mechanical properties, and abundant terminal functional groups, and are widely used in the toughening and modification of materials such as nylon, rubber, and polypropylene. Summary of the Invention

[0004] (I) Technical problem to be solved: In view of the shortcomings of the existing technology, the present invention provides a TPR thermoplastic elastic material with high wear resistance and mechanical properties and a preparation method.

[0005] (II) Technical solution: A high wear-resistant TPR thermoplastic elastomer, comprising: 15-25 parts by weight of SBS styrene-butadiene styrene copolymer, 10-20 parts by weight of filler oil, 15-30 parts by weight of mineral filler, 10-20 parts by weight of compatibilizer, 10-20 parts by weight of monomer resin, and 0.1-1 parts by weight of antioxidant.

[0006] Preferably, the filler oil is white oil, and the mineral filler is any one or a combination of barium sulfate, calcium carbonate, and talc.

[0007] Preferably, the compatibilizer is any one or a combination of maleic anhydride-grafted SEBS and maleic anhydride-grafted POE.

[0008] Preferably, the antioxidant is any one or a combination of antioxidant 1010, antioxidant 1076, and antioxidant 168.

[0009] Preferably, the monomer resin is EASTMAN monomer resin Kristalex 5140.

[0010] A preferred method for preparing a highly wear-resistant TPR thermoplastic elastomer is as follows: SBS styrene-butadiene styrene copolymer, filler oil, mineral filler, compatibilizer, monomer resin, and antioxidant are added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0011] Preferably, the TPR thermoplastic elastomer further includes: 100 parts by weight of SBS styrene-butadiene styrene copolymer, 30-60 parts by weight of nylon 6, 2-10 parts by weight of hyperbranched triazine polyarylamide, 0.3-1.6 parts by weight of maleic anhydride-grafted SBS, 0.6-0.8 parts by weight of antioxidant, 1.4-1.8 parts by weight of stearic acid, and 10-25 parts by weight of filler oil.

[0012] The preferred method for preparing hyperbranched triazine polyarylamide is as follows:

[0013] (1) Add toluene to a reaction flask in a molar ratio of 1:(2.8-3.6):(5-7):(0.02-0.026) of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 4-nitrophenylboronic acid, sodium hydroxide, and bis(triphenylphosphine)palladium dichloride. Heat to 100-110℃ and reflux for 2-3 hours. After filtration, concentrate the filtrate under reduced pressure, wash with water, and add the product to ethanol. Add Pd / C catalyst and hydrazine hydrate solution, heat to 80-85℃, and reflux for 5-10 hours. After filtration and recrystallization purification, obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine; the reaction formula is:

[0014]

[0015] (2) Add N-methylpyrrolidone, pyridine, and 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine in a molar ratio of 1:(1.8-2) to a reaction vessel. Purge with nitrogen gas, heat to 115-125℃, and react for 3-6 hours. After cooling, add an aqueous ethanol solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine-based polyarylamide. The reaction formula is:

[0016]

[0017] (III) Beneficial technical effects: The TPR thermoplastic elastomer prepared by the present invention using SBS styrene-butadiene styrene copolymer, white oil, calcium carbonate, talc and other mineral fillers, maleic anhydride grafted SBS compatibilizer, monomer resin and other raw materials has good tensile properties and hardness.

[0018] Furthermore, the present invention uses 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine and 4-nitrophenylboronic acid as raw materials to prepare a novel AB2 monomer 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and then undergoes a self-condensation reaction to obtain hyperbranched triazine-based polyarylamide.

[0019] This invention uses SBS styrene-butadiene styrene copolymer and nylon 6 as the base material of TPR thermoplastic elastomer, hyperbranched triazine polyarylamide as an additive, and maleic anhydride-grafted SBS as a compatibilizer. The hyperbranched triazine polyarylamide contains a polyamide molecular chain structure, which has good compatibility with nylon 6. At the same time, it contains terminal amino groups, which can react with the anhydride groups of maleic anhydride-grafted SBS, so that it also has good compatibility with SBS styrene-butadiene styrene copolymer. This allows the hyperbranched triazine polyarylamide to be uniformly dispersed in the SBS styrene-butadiene styrene copolymer and nylon 6 thermoplastic elastomer matrix, which significantly improves the tensile strength, elongation at break and Shore A hardness of the elastomer material.

[0020] This invention adds hyperbranched triazine-based polyarylamide to the substrate of thermoplastic elastomers, resulting in a smaller Akron abrasion and better wear resistance of the elastomer material. Furthermore, the hyperbranched triazine-based polyarylamide contains a structurally stable phenyltriazine structure, which has strong heat resistance and is not easily thermally decomposed, thus improving the heat resistance of the elastomer material. Even after high-temperature heat treatment, the material still has a low Akron abrasion and maintains excellent wear resistance. Detailed Implementation

[0021] To make the objectives, technical solutions, and advantages of the invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are for illustrative purposes only and are not intended to limit the invention.

[0022] Pd / C catalyst, palladium content 10%, Wuhan Smike Biotechnology Co., Ltd.

[0023] The preparation method of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine is as follows: In an ice bath, add 10 mL of acetone, 10 mmol of cyanuric chloride, 20 mmol of sodium hydroxide, 10 mmol of 4-hydroxybenzoic acid, and 10 mL of water to a reaction flask. React for 3 h. After the reaction, acidify with hydrochloric acid solution, precipitate the precipitate, filter, wash with water, and dry to obtain 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine. The structural formula is as follows:

[0024] The preparation method of maleic anhydride-grafted SBS is as follows: 30 mL of tetrahydrofuran and 1 g of SBS styrene-butadiene styrene copolymer are added to a reaction flask, followed by the addition of 0.7 g of maleic anhydride and 0.05 g of benzoyl peroxide. The mixture is heated to 65 °C and refluxed for 8 h. After cooling, ethanol is added, the mixture is filtered, washed with ethanol, purified by extraction with acetone, and dried to obtain maleic anhydride-grafted SBS.

[0025] Example 1:

[0026] 150g of SBS styrene-butadiene styrene copolymer, 200g of white oil, 150g of barium sulfate, 100g of compatibilizer maleic anhydride grafted SEBS, 120g of EASTMAN monomer resin Kristalex 5140, and 1g of antioxidant 1010 were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 160℃ for 15min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0027] Example 2:

[0028] 250g of SBS styrene-butadiene styrene copolymer, 160g of white oil, 220g of talc, 200g of compatibilizer maleic anhydride grafted SEBS, 200g of EASTMAN monomer resin Kristalex 5140, and 10g of 1076 were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 160℃ for 15min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0029] Example 3:

[0030] 200g of SBS styrene-butadiene styrene copolymer, 100g of white oil, 300g of calcium carbonate, 120g of compatibilizer maleic anhydride grafted SEBS, 100g of EASTMAN monomer resin Kristalex 5140, and 4g of antioxidant 1010 were added to a twin-screw extruder for melt extrusion, mixed at 160℃ for 20min, and then molded in a flat vulcanizing machine at 160℃ for 15min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0031] Tensile properties were tested according to GB / T528-2009.

[0032] Hardness was tested according to GB / T 531.1-2008.

[0033] Table 1

[0034]

[0035] The present invention also provides the following embodiments.

[0036] Example 4

[0037] (1) Add 30 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 8.4 mmol of 4-nitrophenylboronic acid, 21 mmol of sodium hydroxide, and 0.066 mmol of bis(triphenylphosphine)palladium dichloride to a reaction flask. Heat to 110 °C and reflux for 2 h. After filtration, concentrate the filtrate under reduced pressure, wash with water, and add the product to 80 mL of ethanol. Add 0.22 g of Pd / C catalyst and 2 mL of hydrazine hydrate solution (80% by volume). Heat to 80 °C and reflux for 10 h. After filtration, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine.

[0038] (2) Add 15 mL of N-methylpyrrolidone, 4.2 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 10 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 125 °C, react for 4 h, cool, add an aqueous ethanol solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide.

[0039] (3) 2000g of SBS styrene-butadiene styrene copolymer, 600g of nylon 6, 40g of hyperbranched triazine polyarylamide, 6g of maleic anhydride grafted SBS, 12g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, mixed at 175℃ for 20min, and then molded at 170℃ for 10min in a flat vulcanizing machine with a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0040] Example 5

[0041] (1) Add 40 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 10.8 mmol of 4-nitrophenylboronic acid, 18 mmol of sodium hydroxide, and 0.078 mmol of bis(triphenylphosphine)palladium dichloride to a reaction flask. Heat to 110 °C and reflux for 2 h. After filtration, concentrate the filtrate under reduced pressure. After washing with water, add the product to 80 mL of ethanol, add 0.21 g of Pd / C catalyst and 2.5 mL of hydrazine hydrate solution (80% by volume). Heat to 80 °C and reflux for 8 h. After filtration, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine.

[0042] (2) Add 15 mL of N-methylpyrrolidone, 4.2 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 9 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 120 °C, react for 6 h, cool, add an aqueous ethanol solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide.

[0043] (3) 2000g of SBS styrene-butadiene styrene copolymer, 800g of nylon 6, 100g of hyperbranched triazine polyarylamide, 14g of maleic anhydride grafted SBS, 16g of antioxidant 1076 and 28g of stearic acid were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 170℃ for 10min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0044] Example 6

[0045] (1) Add 40 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 9.6 mmol of 4-nitrophenylboronic acid, 15 mmol of sodium hydroxide, and 0.06 mmol of bis(triphenylphosphine)palladium dichloride to a reaction flask. Heat to 100 °C and reflux for 3 h. After filtration, concentrate the filtrate under reduced pressure, wash with water, and add the product to 100 mL of ethanol. Add 0.18 g of Pd / C catalyst and 2.1 mL of hydrazine hydrate solution (80% by volume). Heat to 85 °C and reflux for 6 h. After filtration, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine.

[0046] (2) Add 15 mL of N-methylpyrrolidone, 3 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 9.6 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 115 °C, react for 6 h, cool, add ethanol aqueous solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide.

[0047] (3) 2000g of SBS styrene-butadiene styrene copolymer, 1000g of nylon 6, 150g of hyperbranched triazine polyarylamide, 23g of maleic anhydride grafted SBS, 16g of antioxidant 1076 and 31g of stearic acid were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 170℃ for 10min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0048] Example 7

[0049] (1) 2000g of SBS styrene-butadiene styrene copolymer, 1200g of nylon 6, 200g of hyperbranched triazine polyarylamide, 32g of maleic anhydride grafted SBS, 16g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 170℃ for 10min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0050] Comparative Example 1

[0051] (1) 2000g of SBS styrene-butadiene styrene copolymer, 600g of nylon 6, 6g of maleic anhydride grafted SBS, 12g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, mixed at 175℃ for 20min, and then molded at 170℃ for 10min in a flat vulcanizing machine with a pressure of 10MPa to obtain a high wear-resistant TPR thermoplastic elastomer.

[0052] Comparative Example 2

[0053] (1) 2000g of SBS styrene-butadiene styrene copolymer, 600g of nylon 6, 40g of hyperbranched triazine polyarylamide, 12g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, mixed at 175℃ for 20min, and then molded at 170℃ for 10min in a flat vulcanizing machine with a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0054] Comparative Example 3

[0055] (1) Add 15 mL of N-methylpyrrolidone, 4.2 mL of pyridine, 5 mmol of 5-aminoisophthalic acid, and 10 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 125 °C, react for 4 h, cool, add an aqueous ethanol solution, filter, wash with ethanol, and dry to obtain hyperbranched polyarylamide.

[0056] (2) 2000g of SBS styrene-butadiene styrene copolymer, 600g of nylon 6, 40g of hyperbranched polyarylamide, 6g of maleic anhydride-grafted SBS, 12g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, mixed at 175℃ for 20min, and then molded at 170℃ for 10min in a flat vulcanizing machine with a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

[0057] Test specimens were made from highly abrasion-resistant TPR thermoplastic elastomer.

[0058] Abrasion resistance was tested according to GB / T 1689-2014. The TPR thermoplastic elastomer was heat-treated at 150℃ for 48 hours, and then cooled before abrasion resistance testing.

[0059] Tensile properties were tested according to GB / T528-2009.

[0060] Hardness was tested according to GB / T 531.1-2008.

[0061] The test results are shown in Table 2-3.

[0062] Table 2: Akron wear before and after heat treatment

[0063]

[0064] Table 3: Tensile strength, elongation at break, and hardness

[0065]

[0066]

[0067] After testing, compared with Comparative Example 1, the TPR thermoplastic elastomer materials of Examples 1-4 contain hyperbranched triazine polyarylamide, which has a polyamide molecular chain structure and good compatibility with nylon 6. At the same time, it contains terminal amino groups, which can react with the anhydride groups of maleic anhydride-grafted SBS, so that maleic anhydride-grafted SBS acts as a compatibilizer, improving the compatibility between hyperbranched triazine polyarylamide and SBS styrene-butadiene styrene copolymer. This makes the hyperbranched triazine polyarylamide uniformly dispersed in the thermoplastic elastomer matrix of SBS styrene-butadiene styrene copolymer and nylon 6, which is beneficial to improving the tensile strength, elongation at break and Shore A hardness of the elastomer material. Furthermore, the addition of hyperbranched triazine polyarylamide reduces Akron abrasion and improves wear resistance in elastomer materials. At the same time, the hyperbranched triazine polyarylamide contains a structurally stable phenyltriazine structure, which has strong heat resistance and is not easily thermally decomposed, thus improving the heat resistance of elastomer materials. Even after high-temperature heat treatment, the material still has a low Akron abrasion and maintains excellent wear resistance.

[0068] Comparative Example 2 did not include maleic anhydride-grafted SBS. The compatibility between the hyperbranched triazine polyarylamide and the SBS styrene-butadiene styrene copolymer was poor, resulting in poor dispersion of the hyperbranched triazine polyarylamide in the elastomer matrix. The tensile strength, elongation at break, Shore A hardness and other mechanical properties of the material were lower than those of Examples 1-4.

[0069] Comparative Example 3 uses existing 5-aminoisophthalic acid to prepare hyperbranched polyarylamide, which is added to the SBS styrene-butadiene styrene copolymer and nylon 6 thermoplastic elastomer matrix. The tensile strength, elongation at break, Shore A hardness and other mechanical properties of the material are significantly improved. The Akron abrasion is low and the wear resistance is good. However, it does not contain the heat-resistant phenyltriazine structure, so the heat resistance of the material is poor. After heat treatment, the Akron abrasion of the material increases significantly and the wear resistance deteriorates.

Claims

1. A method for preparing a highly wear-resistant TPR thermoplastic elastomer, characterized in that, Includes the following steps: (1) Add 30 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 8.4 mmol of 4-nitrophenylboronic acid, 21 mmol of sodium hydroxide, and 0.066 mmol of bis(triphenylphosphine)palladium dichloride to the reaction flask, heat to 110 °C, reflux for 2 h, filter, concentrate the filtrate under reduced pressure, wash with water, add the product to 80 mL of ethanol, add 0.22 g of Pd / C catalyst and 2 mL of hydrazine hydrate solution (volume fraction of 80%), heat to 80 °C, reflux for 10 h, filter, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine; (2) Add 15 mL of N-methylpyrrolidone, 4.2 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 10 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 125 °C, react for 4 h, cool, add an aqueous ethanol solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide; (3) 2000g of SBS styrene-butadiene styrene copolymer, 600g of nylon 6, 40g of hyperbranched triazine polyarylamide, 6g of maleic anhydride grafted SBS, 12g of antioxidant 1010 and 36g of stearic acid were added to a twin-screw extruder for melt extrusion, mixed at 175°C for 20min, and then molded at 170°C for 10min in a flat vulcanizing machine with a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

2. A method for preparing a highly wear-resistant TPR thermoplastic elastomer, characterized in that, Includes the following steps: (1) Add 40 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 10.8 mmol of 4-nitrophenylboronic acid, 18 mmol of sodium hydroxide, and 0.078 mmol of bis(triphenylphosphine)palladium dichloride to the reaction flask. Heat to 110 °C and reflux for 2 h. After filtration, concentrate the filtrate under reduced pressure. After washing with water, add the product to 80 mL of ethanol, add 0.21 g of Pd / C catalyst and 2.5 mL of hydrazine hydrate solution with a volume fraction of 80%. Heat to 80 °C and reflux for 8 h. After filtration, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine. (2) Add 15 mL of N-methylpyrrolidone, 4.2 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 9 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 120 °C, react for 6 h, cool, add ethanol aqueous solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide; (3) 2000g of SBS styrene-butadiene styrene copolymer, 800g of nylon 6, 100g of hyperbranched triazine polyarylamide, 14g of maleic anhydride grafted SBS, 16g of antioxidant 1076 and 28g of stearic acid were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 170°C for 10min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

3. A method for preparing a highly wear-resistant TPR thermoplastic elastomer, characterized in that, Includes the following steps: 1) Add 40 mL of toluene, 3 mmol of 2-(4-carboxyphenoxy)-4,6-dichloro-1,3,5-triazine, 9.6 mmol of 4-nitrophenylboronic acid, 15 mmol of sodium hydroxide, and 0.06 mmol of bis(triphenylphosphine)palladium dichloride to a reaction flask. Heat to 100 °C and reflux for 3 h. After filtration, concentrate the filtrate under reduced pressure, wash with water, and add the product to 100 mL of ethanol. Add 0.18 g of Pd / C catalyst and 2.1 mL of hydrazine hydrate solution (80% by volume). Heat to 85 °C and reflux for 6 h. After filtration, recrystallize and purify to obtain 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine. (2) Add 15 mL of N-methylpyrrolidone, 3 mL of pyridine, 5 mmol of 2-(4-carboxyphenoxy)-4,6-bis(4-aminophenyl)-1,3,5-triazine, and 9.6 mmol of triphenyl phosphite to the reaction vessel, purge with nitrogen, heat to 115 °C, react for 6 h, cool, add ethanol aqueous solution, filter, wash with ethanol, and dry to obtain hyperbranched triazine polyarylamide; (3) 2000g of SBS styrene-butadiene styrene copolymer, 1000g of nylon 6, 150g of hyperbranched triazine polyarylamide, 23g of maleic anhydride grafted SBS, 16g of antioxidant 1076 and 31g of stearic acid were added to a twin-screw extruder for melt extrusion, and then molded in a flat vulcanizing machine at 170°C for 10min at a pressure of 10MPa to obtain a highly wear-resistant TPR thermoplastic elastomer.

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