Preparation method and application of super weather-resistant HAA-cured matte polyester resin

Abstract

The present invention relates to the technical field of polyester resins, and discloses a preparation method and application of a super-weather-resistant HAA-cured matte polyester resin. The present invention reacts neopentyl glycol, triazine phenylimide diol monomer, dibasic acid, esterification catalyst, onium salt curing accelerator, etc. to obtain a super-weather-resistant HAA-cured matte polyester resin. The triazine phenylimide diol monomer has a phenylimide ring and a triazine ring structure with heat resistance and structural stability, which is beneficial to improving the high temperature resistance and mechanical strength of the polyester resin powder coating film, showing higher impact resistance, and contains a dialkyl side chain. After being introduced into the polyester molecular chain, steric hindrance and shielding effects can be generated, inhibiting the contact between water molecules and ester bonds in the polyester molecular chain, reducing the hydrolysis reaction of the ester group, thereby improving the hydrolysis resistance of the polyester resin. And the anti-ultraviolet aging performance of the paint film is improved, and the weather resistance and light retention rate are high.

Description

Technical Field

[0001] The invention relates to the technical field of polyester resins, and in particular to a preparation method and application of a super-weather-resistant HAA-cured matting polyester resin. Background Art

[0002] Polyester resins are mainly made of polyols, polyacids, etc. through esterification and polycondensation reactions, and have good heat resistance, mechanical strength, corrosion resistance and other properties. It can be made into powder coatings, solvent-based coatings, adhesives, etc., and is widely used in building materials, outdoor furniture equipment, transportation facilities, etc. Improving the water resistance, heat resistance, weather resistance and other properties of polyester resins and their powder coatings has important applications. The Chinese invention patent with announcement number CN115626978B discloses a polyester resin for powder coatings and its preparation method and application. Diamines, maleic anhydride, acrylic ester monomers, polyols, polyacids, acidolysis agents, etc. are used as raw materials, and bismaleimide structures and acrylic resin structures are used to modify polyester resins. The obtained powder coating has good storage stability, weather resistance and heat resistance, but the polyester resin powder coating does not have good hydrolysis resistance, impact resistance and other properties. Summary of the invention

[0003] The invention solves the problem that the polyester resin has poor weather resistance, water resistance, heat resistance and other properties.

[0004] Technical solution: A method for preparing a super weather-resistant HAA-cured matte polyester resin, comprising: sequentially adding a polyol, a dibasic acid and an esterification catalyst into a reaction kettle, introducing nitrogen, heating while stirring, firstly keeping the temperature at 165-185°C for 1-2h, then heating to 240-250°C, keeping the temperature for 12-16h, discharging water generated by the esterification reaction, adding an acidolysis agent when the acid value reaches 5-20 mgKOH / g, and reacting for 3-4h; when the acid value reaches 50-70 mg KOH / g, vacuuming for condensation reaction for 2-3h; when the acid value reaches 40-50 mg KOH / g, adding an onium salt curing accelerator and an antioxidant, stirring for 20-40 min, discharging, cooling, and crushing to obtain a super weather-resistant HAA-cured matte polyester resin.

[0005] Preferably, the polyol is a combination of neopentyl glycol and triazine phenylimide diol monomers; the structural formula of the triazine phenylimide diol monomer is .

[0006] Preferably, the amount of polyol is 34-42 parts by weight, the dibasic acid is 48-50 parts by weight, the acidolysis agent is 20-28 parts by weight, the esterification catalyst is 0.5-0.6 parts by weight, the antioxidant is 0.4-0.5 parts by weight, and the onium salt curing accelerator is 0.1-0.13 parts by weight.

[0007] Preferably, the dibasic acid is terephthalic acid; the acidolysis agent includes any one of isophthalic acid, 1,4-cyclohexanedicarboxylic acid, and trimethylolpropane.

[0008] Preferably, the antioxidant is any one or a combination of hindered phenol antioxidants and phosphite antioxidants; the esterification catalyst is monobutyltin oxide, and the onium salt curing accelerator is triphenylethylphosphonium bromide.

[0009] Preferably, the method for preparing the triazine phenylimide diol monomer comprises:

[0010] (1) Add N,N-dimethylformamide, 100 parts by weight of 2-chloro-4,6-diamino-1,3,5-triazine, 89-128 parts by weight of dialkylamine, and 95-104 parts by weight of potassium carbonate to a reaction vessel equipped with a condenser reflux tube, introduce nitrogen, raise the temperature to 130-140°C, stir and react for 24-30 hours, pour the solution into water, filter, wash the filter cake with petroleum ether, and recrystallize the product with a mixed solution of petroleum ether and tetrahydrofuran to obtain 2-(alkylamine)-4,6-diamino-1,3,5-triazine. The structural formula of dialkylamine is , n is any integer between 4 and 8. The reaction formula is: .

[0011] (2) Add N-methylpyrrolidone, 100 parts by weight of 2-(alkylamine)-4,6-diamino-1,3,5-triazine, and 112-156 parts by weight of 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, heat to 180-195°C, stir and react for 8-12 hours, pour the solution into water, filter, and recrystallize the product with ethanol to obtain triazine phenylimide diol monomer. The reaction formula is: .

[0012] Preferably, the super weather-resistant HAA-cured matte polyester resin is used in powder coatings, which include 62-68 parts by weight of super weather-resistant HAA-cured matte polyester resin, 5.2-6 parts by weight of HAA hydroxyalkylamide curing agent, 0.9-1.2 parts by weight of leveling agent, 2.6-3.5 parts by weight of matting agent benzoin, 26-32 parts by weight of filler carbon black, and any one or combination of barium sulfate.

[0013] Technical effect: The present invention prepares triazine phenylimide diol monomer, and carries out co-esterification polymerization reaction with neopentyl glycol, terephthalic acid, etc. to obtain super weather-resistant HAA curing type matting polyester resin, and compounding with HAA hydroxyalkylamide curing agent, matting agent benzoin, filler, etc. to obtain polyester resin powder coating. The polyester resin contains triazine phenylimide diol monomer, which has phenylimide ring and triazine ring structure with heat resistance and structural stability, which is beneficial to improve the high temperature resistance and mechanical strength of the paint film, and shows higher impact resistance. It also contains dialkyl side chains, which can produce steric hindrance and shielding effects after being introduced into the polyester molecular chain, inhibiting the contact between water molecules and ester bonds in the polyester molecular chain, reducing the hydrolysis reaction of the ester group, thereby improving the hydrolysis resistance of the polyester resin. After high-temperature boiling, the polyester resin paint film has no blistering and cracking. In addition, the paint film has better anti-ultraviolet aging performance, high weather resistance and high light retention rate. DETAILED DESCRIPTION

[0014] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0015] Embodiment 1:

[0016] (1) In a reaction vessel equipped with a reflux tube, 200 mL of N,N-dimethylformamide, 2 g of 2-chloro-4,6-diamino-1,3,5-triazine, 2.28 g of di-n-hexylamine, and 2.08 g of potassium carbonate were added, nitrogen was introduced, the temperature was raised to 130°C, and the reaction was stirred for 24 h. The solution was poured into water and filtered, and the filter cake was washed with petroleum ether. The product was recrystallized from a mixed solution of petroleum ether and tetrahydrofuran to obtain 2-(alkylamine)-4,6-diamino-1,3,5-triazine.

[0017] (2) Add 30 mL of N-methylpyrrolidone, 4 g of 2-(alkylamine)-4,6-diamino-1,3,5-triazine, and 5.28 g of 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, raise the temperature to 195°C, stir and react for 8 h, pour the solution into water, filter with suction, and recrystallize the product with ethanol to obtain a triazine phenylimide diol monomer.

[0018] (3) 30 g of neopentyl glycol, 4 g of triazine phenylimide diol monomer, 48 g of terephthalic acid and 0.5 g of esterification catalyst monobutyl tin oxide were added to the reactor in sequence, nitrogen was introduced, and the temperature was raised while stirring. The reaction was first kept at 170°C for 2 h, and then the temperature was raised to 240°C and kept for 16 h. The water generated by the esterification reaction was discharged. When the acid value reached 20 mg KOH / g, an acidolysis agent consisting of 21 g of isophthalic acid, 5 g of 1,4-cyclohexanedicarboxylic acid and 2 g of trimethylolpropane was added and the reaction was continued for 4 h. When the acid value reached 60 mg KOH / g, vacuum was drawn to carry out polycondensation reaction for 2 h. When the acid value reached 50 mg KOH / g, 0.12 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.35 g of antioxidant hindered phenol antioxidant 1076 and 0.15 g of phosphite antioxidant 168 were added and stirred for 20 min. min, discharging, cooling and crushing to obtain super weather-resistant HAA-curing matte polyester resin.

[0019] Embodiment 2:

[0020] (1) In a reaction vessel equipped with a reflux tube, 200 mL of N,N-dimethylformamide, 2 g of 2-chloro-4,6-diamino-1,3,5-triazine, 2.56 g of di-n-octylamine, and 1.9 g of potassium carbonate were added, nitrogen was introduced, the temperature was raised to 140°C, and the reaction was stirred for 24 h. The solution was poured into water and filtered, and the filter cake was washed with petroleum ether. The product was recrystallized from a mixed solution of petroleum ether and tetrahydrofuran to obtain 2-(alkylamine)-4,6-diamino-1,3,5-triazine.

[0021] (2) Add 40 mL of N-methylpyrrolidone, 4 g of 2-(alkylamine)-4,6-diamino-1,3,5-triazine, and 4.48 g of 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, raise the temperature to 180°C, stir and react for 12 h, pour the solution into water, filter with suction, and recrystallize the product with ethanol to obtain a triazine phenylimide diol monomer.

[0022] (3) 30 g of neopentyl glycol, 8 g of triazine phenylimide diol monomer, 49.2 g of terephthalic acid and 0.6 g of esterification catalyst monobutyl tin oxide were added to the reactor in sequence, nitrogen was introduced, and the temperature was raised while stirring. The reaction was first kept at 185°C for 1 h, and then the temperature was raised to 250°C and kept for 12 h. The water generated by the esterification reaction was discharged. When the acid value reached 5 mg KOH / g, an acidolysis agent consisting of 15 g of isophthalic acid, 4 g of 1,4-cyclohexanedicarboxylic acid and 1 g of trimethylolpropane was added and the reaction was continued for 4 h. When the acid value reached 70 mg KOH / g, vacuum was drawn to carry out polycondensation reaction for 3 h. When the acid value reached 50 mg KOH / g, 0.13 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.28 g of antioxidant hindered phenol antioxidant 1076 and 0.12 g of phosphite antioxidant 168 were added and stirred for 20 min. min, discharging, cooling and crushing to obtain super weather-resistant HAA-curing matte polyester resin.

[0023] Embodiment 3:

[0024] (1) In a reaction vessel equipped with a reflux tube, 150 mL of N,N-dimethylformamide, 2 g of 2-chloro-4,6-diamino-1,3,5-triazine, 1.78 g of di-n-butylamine, and 1.9 g of potassium carbonate were added, nitrogen was introduced, the temperature was raised to 140°C, and the reaction was stirred for 24 h. The solution was poured into water and filtered, and the filter cake was washed with petroleum ether. The product was recrystallized from a mixed solution of petroleum ether and tetrahydrofuran to obtain 2-(alkylamine)-4,6-diamino-1,3,5-triazine.

[0025] (2) Add 30 mL of N-methylpyrrolidone, 4 g of 2-(alkylamine)-4,6-diamino-1,3,5-triazine, and 6.24 g of 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, raise the temperature to 180°C, stir and react for 12 h, pour the solution into water, filter with suction, and recrystallize the product with ethanol to obtain a triazine phenylimide diol monomer.

[0026] (3) Add 30 g of neopentyl glycol, 12 g of triazine phenylimide diol monomer, 50 g of terephthalic acid and 0.6 g of esterification catalyst monobutyl tin oxide to the reactor in sequence, introduce nitrogen, and heat while stirring. First, keep the temperature at 165°C for 2 h, then heat to 250°C and keep the temperature for 12 h. Discharge the water generated by the esterification reaction. When the acid value reaches 20 mg KOH / g, add an acidolysis agent consisting of 18 g of isophthalic acid, 4 g of 1,4-cyclohexanedicarboxylic acid and 1.6 g of trimethylolpropane, and react for 4 h. When the acid value reaches 50 mg KOH / g, vacuumize and carry out polycondensation for 3 h. When the acid value reaches 40 mg KOH / g, add 0.1 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.28 g of antioxidant hindered phenol antioxidant 1076 and 0.12 g of phosphite antioxidant 168, and stir for 20 min. min, discharging, cooling and crushing to obtain super weather-resistant HAA-curing matte polyester resin.

[0027] Comparative Example 1:

[0028] (1) 34 g of neopentyl glycol, 48 g of terephthalic acid and 0.5 g of esterification catalyst monobutyl tin oxide were added to a reaction kettle in sequence, nitrogen was introduced, and the temperature was raised while stirring. The reaction was first kept at 170°C for 2 h, and then the temperature was raised to 240°C and kept for 16 h. The water generated by the esterification reaction was discharged. When the acid value reached 20 mg KOH / g, an acidolysis agent consisting of 21 g of isophthalic acid, 5 g of 1,4-cyclohexanedicarboxylic acid and 2 g of trimethylolpropane was added and the reaction was continued for 4 h. When the acid value reached 60 mg KOH / g, vacuum was drawn to carry out polycondensation reaction for 2 h. When the acid value reached 50 mg KOH / g, 0.12 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.35 g of antioxidant hindered phenol antioxidant 1076 and 0.15 g of phosphite antioxidant 168 were added, and the mixture was stirred for 20 min. The mixture was discharged, cooled and crushed to obtain a polyester resin.

[0029] Comparative Example 2:

[0030] (1) Add 30 mL of N-methylpyrrolidone, 4 g of p-phenylenediamine, and 5.28 g of 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, heat to 195°C, stir and react for 8 hours, pour the solution into water, filter, and recrystallize the product with ethanol to obtain a phenylimide diol monomer. The structural formula is:

[0031] .

[0032] (2) 30 g of neopentyl glycol, 4 g of phenylimide diol monomer, 48 g of terephthalic acid and 0.5 g of esterification catalyst monobutyl tin oxide were added to the reactor in sequence, nitrogen was introduced, and the temperature was raised while stirring. The reaction was first kept at 170°C for 2 h, and then the temperature was raised to 240°C and kept for 16 h. The water generated by the esterification reaction was discharged. When the acid value reached 20 mg KOH / g, an acidolysis agent consisting of 21 g of isophthalic acid, 5 g of 1,4-cyclohexanedicarboxylic acid and 2 g of trimethylolpropane was added and the reaction was continued for 4 h. When the acid value reached 60 mg KOH / g, vacuum was drawn to carry out polycondensation reaction for 2 h. When the acid value reached 50 mg KOH / g, 0.12 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.35 g of antioxidant hindered phenol antioxidant 1076 and 0.15 g of phosphite antioxidant 168 were added and stirred for 20 min. min, discharging, cooling and crushing to obtain super weather-resistant HAA-curing matte polyester resin.

[0033] Comparative Example 3:

[0034] (1) Add 30 mL of N-methylpyrrolidone and 4 g of 4,6-dichloro-2-dimethylamino-1,3,5-triazine (CAS No. 2401-64-1, structural formula: ), 5.28g 4-hydroxyphthalic anhydride, heated to 195°C, stirred for 8h, poured the solution into water, filtered, and the product was recrystallized from ethanol to obtain triazine phenylimide diol monomer. The structural formula is .

[0035] (2) 30 g of neopentyl glycol, 4 g of triazine phenylimide diol monomer, 48 g of terephthalic acid and 0.5 g of esterification catalyst monobutyl tin oxide were added to the reactor in sequence, nitrogen was introduced, and the temperature was raised while stirring. The reaction was first kept at 170°C for 2 h, and then the temperature was raised to 240°C and kept for 16 h. The water generated by the esterification reaction was discharged. When the acid value reached 20 mg KOH / g, an acidolysis agent consisting of 21 g of isophthalic acid, 5 g of 1,4-cyclohexanedicarboxylic acid and 2 g of trimethylolpropane was added and the reaction was continued for 4 h. When the acid value reached 60 mg KOH / g, vacuum was drawn to carry out polycondensation reaction for 2 h. When the acid value reached 50 mg KOH / g, 0.12 g of onium salt curing accelerator triphenylethyl phosphonium bromide, 0.35 g of antioxidant hindered phenol antioxidant 1076 and 0.15 g of phosphite antioxidant 168 were added and stirred for 20 min. min, discharging, cooling and crushing to obtain super weather-resistant HAA-curing matte polyester resin.

[0036] Refer to GB / T 6743-2008 standard to test the acid value of polyester resin.

[0037] The viscosity of the polyester resin was tested using a viscometer with the temperature set at 200°C. After the temperature stabilized, a polyester resin sample was taken and placed in the center of the test table of the viscometer for viscosity measurement.

[0038] The polyester sample was tested by differential scanning calorimetry. 10 mg of polyester resin sample was weighed and placed on the stage. After setting the parameters in the program, DSC measurement was performed. The measurement temperature range was 25-100°C and the heating rate was 10°C / min. The test results are shown in Table 1.

[0039] Table 1 Polyester resin performance test

[0040] Acid value (mg KOH / g) Viscosity (mPa.s) Glass transition temperature (℃) Example 1 52.3 2617 70.8 Example 2 51.9 2850 75.0 Example 3 47.4 2892 77.9 Comparative Example 1 52.1 2521 62.8 Comparative Example 2 51.7 2949 69.2 Comparative Example 3 52.8 2865 71.3

[0041] After testing, the polyester resins prepared in each embodiment have moderate acid values ​​and viscosity values. In addition, embodiments 1-3 and comparative example 3 have higher glass transition temperatures, mainly because triazine phenyl imide diol has thermally stable imide rings and triazine rings, which are introduced into the polyester molecular chain to increase the glass transition temperature of the polyester resin and improve the heat resistance.

[0042] Example 4: 650 g of super weather-resistant HAA-cured matte polyester resin (prepared according to the method of Example 1), 9 g of leveling agent, 26 g of matting agent benzoin, 310 g of barium sulfate, 10 g of carbon black, and 55 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0043] Example 5: 680 g of super weather-resistant HAA-cured matte polyester resin (prepared according to the method of Example 2), 12 g of leveling agent, 35 g of matting agent benzoin, 254 g of barium sulfate, 6 g of carbon black, and 60 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0044] Example 6: 620 g of super weather-resistant HAA-cured matte polyester resin (prepared according to the method of Example 3), 9 g of leveling agent, 30 g of matting agent benzoin, 275 g of barium sulfate, 6 g of carbon black, and 52 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0045] Comparative Example 4: 650 g of polyester resin (prepared according to the method of Comparative Example 1), 9 g of leveling agent, 26 g of matting agent benzoin, 310 g of barium sulfate, 10 g of carbon black, and 55 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0046] Comparative Example 5: 650 g of polyester resin (prepared according to the method of Comparative Example 2), 9 g of leveling agent, 26 g of matting agent benzoin, 310 g of barium sulfate, 10 g of carbon black, and 55 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0047] Comparative Example 6: 650 g of polyester resin (prepared according to the method of Comparative Example 3), 9 g of leveling agent, 26 g of matting agent benzoin, 310 g of barium sulfate, 10 g of carbon black, and 55 g of HAA hydroxyalkylamide curing agent were stirred and mixed to obtain a powder coating.

[0048] The powder coating was extruded, tableted, and crushed through a twin-screw extruder, then passed through a 200-mesh sieve, and then sprayed on the substrate by electrostatic spraying and cured at 180°C for 15 minutes. The boiling water immersion test was tested according to GB / T 1733-1993 standard, and the boiling water was boiled for 96 hours.

[0049] The impact resistance of the paint film was tested according to GB / T 1732-2020. The thickness of the paint film was 70um.

[0050] Adhesion grade tested according to GB / T 9286-2021 standard.

[0051] The 60° mirror gloss of the paint film was tested according to GB / T 9754-2007 standard. The paint film was placed in a UV aging test chamber with a 340nm UV lamp as the light source for 720 hours of artificial accelerated aging. The 60° mirror gloss was tested and the gloss retention rate was calculated. The test results are shown in Table 2.

[0052] Table 2 Powder coating performance test

[0053]

[0054] After testing, compared with comparative examples 4-6, the powder coating of Example 4-6 has better water boiling resistance, excellent heat resistance and hydrolysis resistance, and artificial accelerated aging, high light retention rate of the paint film, strong weather resistance, and high impact resistance. This is mainly because the polyester resin of Example 4-6 contains triazine phenylimide diol monomers, which have phenylimide rings and triazine ring structures with heat resistance and structural stability, which are beneficial to improving the high temperature resistance and mechanical strength of the paint film, showing higher impact resistance, and contains dialkyl side chains. After being introduced into the polyester molecular chain, it can produce steric hindrance and shielding effects, inhibit the contact between water molecules and ester bonds in the polyester molecular chain, reduce the hydrolysis reaction of ester groups, thereby improving the hydrolysis resistance of the polyester resin. After high-temperature water boiling, the polyester resin paint film has no blistering and cracking. The paint film has better anti-ultraviolet aging performance, high weather resistance and light retention rate.

Claims

1. A method for preparing a super weather-resistant HAA-cured matte polyester resin, characterized in that: The preparation method comprises: adding polyol, dibasic acid and esterification catalyst to a reaction kettle in sequence, introducing nitrogen, raising the temperature while stirring, first keeping the temperature at 165-185° C. for 1-2 hours, then raising the temperature to 240-250° C. for 12-16 hours, discharging water generated by the esterification reaction, adding an acidolysis agent when the acid value reaches 5-20 mg KOH / g, and reacting for 3-4 hours; when the acid value reaches 50-70 mg KOH / g, vacuuming for condensation reaction for 2-3 hours; when the acid value reaches 40-50 mg KOH / g, adding an onium salt curing accelerator and an antioxidant, stirring for 20-40 minutes, discharging, cooling and crushing to obtain a super-weather-resistant HAA-curing type matte polyester resin; The polyol is a combination of neopentyl glycol and triazine phenylimide diol monomers; The structural formula of the triazine phenylimide diol monomer is: , n is any integer between 4 and 8.

2. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 1, characterized in that: The dosage of the polyol is 34-42 parts by weight, the dibasic acid is 48-50 parts by weight, the acidolysis agent is 20-28 parts by weight, the esterification catalyst is 0.5-0.6 parts by weight, the antioxidant is 0.4-0.5 parts by weight, and the onium salt curing accelerator is 0.1-0.13 parts by weight.

3. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 2, characterized in that: The dibasic acid is terephthalic acid; the acidolysis agent includes any one or a combination of isophthalic acid, 1,4-cyclohexanedicarboxylic acid, and trimethylolpropane.

4. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 2, characterized in that: The antioxidant is any one or a combination of hindered phenol antioxidants and phosphite antioxidants; the esterification catalyst is monobutyl tin oxide; and the onium salt curing accelerator is triphenylethyl phosphonium bromide.

5. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 1, characterized in that: The preparation method of the triazine phenylimide diol monomer comprises: (1) Add N,N-dimethylformamide, 2-chloro-4,6-diamino-1,3,5-triazine, dialkylamine and potassium carbonate to a reaction vessel equipped with a condenser reflux tube, introduce nitrogen, heat to 130-140°C, stir and react for 24-30 hours, pour the solution into water, filter with suction, wash the filter cake, and recrystallize the product to obtain 2-(alkylamine)-4,6-diamino-1,3,5-triazine; (2) Add N-methylpyrrolidone, 2-(alkylamine)-4,6-diamino-1,3,5-triazine and 4-hydroxyphthalic anhydride to a reaction vessel equipped with a condenser reflux tube, raise the temperature to 180-195° C., stir and react for 8-12 hours, pour the solution into water, filter with suction, and recrystallize the product to obtain a triazine phenylimide diol monomer; The structural formula of the dialkylamine is , n is any integer between 4 and 8.

6. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 5, characterized in that: In the above (1), the amount of 2-chloro-4,6-diamino-1,3,5-triazine is 100 parts by weight, the amount of dialkylamine is 89-128 parts by weight, and the amount of potassium carbonate is 95-104 parts by weight.

7. The method for preparing the super weather-resistant HAA-cured matte polyester resin according to claim 5, characterized in that: In the above (2), the amount of 2-(alkylamine)-4,6-diamino-1,3,5-triazine is 100 parts by weight, and the amount of 4-hydroxyphthalic anhydride is 112-156 parts by weight.

8. Application of the super weather-resistant HAA-curing matte polyester resin obtained by the preparation method according to any one of claims 1 to 7 in powder coatings, characterized in that: The powder coating comprises 62-68 parts by weight of super weather-resistant HAA-curing matting polyester resin, 5.2-6 parts by weight of HAA hydroxyalkylamide curing agent, 0.9-1.2 parts by weight of leveling agent, 2.6-3.5 parts by weight of matting agent and 26-32 parts by weight of filler.

9. The use of the super weather-resistant HAA-curing matte polyester resin in powder coatings according to claim 8, characterized in that: The matting agent is benzoin; the filler includes any one or a combination of carbon black and barium sulfate.

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