CN114958156A - Preparation method and application of coating curing agent - Google Patents
Preparation method and application of coating curing agent Download PDFInfo
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- CN114958156A CN114958156A CN202210665755.8A CN202210665755A CN114958156A CN 114958156 A CN114958156 A CN 114958156A CN 202210665755 A CN202210665755 A CN 202210665755A CN 114958156 A CN114958156 A CN 114958156A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
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Abstract
The invention provides a preparation method of a coating curing agent, which comprises the steps of reacting isocyanuric acid with chloropropene in a mixed liquid of an organic solvent and alkali to synthesize triallyl phenyl isocyanurate, oxidizing and synthesizing into triglycidyl isocyanurate under the condition of a catalyst, wherein the triglycidyl isocyanurate is high in purity and basically does not contain Epoxy Chloropropane (ECH), and the preparation of the curing agent does not use the epoxy chloropropane with carcinogenicity as a raw material; hydrogen peroxide is used as an oxygen source, and a small amount of harmless water is generated by reaction and is easy to treat; the curing agent has high preparation yield, has advantages in the characteristics of coating film gloss, corrosion resistance, gloss retention, solvent resistance, high temperature resistance and the like, and is obviously a better choice besides TGIC and HAA.
Description
Technical Field
The invention belongs to the technical field of powder coating, and particularly relates to a preparation method and application of a coating curing agent.
Background
At present, the powder coating is an environment-friendly coating, and the development is rapid in recent years. The curing agent used in the polyester powder coating is triglycidyl isocyanurate (TGIC) and hydroxyalkyl amide (HAA) in the most amount.
TGIC was developed earlier and is highly functional, but it is irritating to the skin and eyes and therefore prone to skin allergy during powder coating production and spraying, which affects the health of the staff. HAA is not irritant, so that it has been substituted for TGIC to become the most used curing agent for weather-resistant powder coating. However, HAA has certain characteristics that are not as good as TGIC, which limits its application range. Therefore, HAA cannot completely replace TGIC in other regions except Europe, which is well known for environmental protection.
Currently, the process for the manufacture of TGIC is mainly obtained by reacting isocyanuric acid with epichlorohydrin. However, this method uses a large amount of Epichlorohydrin (ECH) and has the following disadvantages:
1. the raw material epichlorohydrin has irritation, toxicity and carcinogenicity;
2. the residual chloride ions in the product affect the electrical property of the product, have great limitation on the application of electronic materials, and can be used only by purifying and removing the chloride ions at a high cost;
3. the overall yield is low (about 80%).
Therefore, there is a need to develop a safe, environment-friendly, high-yield production method, and the product has wide industrial applicability.
Disclosure of Invention
The invention provides a preparation method for synthesizing triallyl isocyanurate and then synthesizing a coating curing agent containing glycidyl isocyanurate under certain conditions by using isocyanuric acid and chloropropene to solve the defects in the prior art;
a preparation method of a coating curing agent comprises the following steps:
s1, adding isocyanuric acid into a mixed solution containing an organic solvent and alkali, uniformly mixing, adding chloropropene, stirring for 2-4 hours at the temperature of 40-80 ℃, and uniformly mixing to obtain triallyl isocyanurate;
s2, adding a water solution containing a first catalyst, adjusting the pH value, adding triallyl isocyanurate, a surfactant and hydrogen peroxide obtained in the step S1, uniformly mixing at the temperature of 50-80 ℃, reacting for 12-24 hours to obtain a crude product, and reacting to generate a small amount of harmless water by taking the hydrogen peroxide as an oxygen source to be easily treated;
and S3, adding an extraction solvent into the crude product, layering, collecting an organic layer, cooling, crystallizing, and performing suction filtration to obtain the coating curing agent.
The preparation method of the coating curing agent comprises the step of preparing the coating curing agent, wherein the coating curing agent comprises triglycidyl isocyanurate with the structural formula (B)
And/or allyl diglycidylester of isocyanuric acid of the formula (C)
The triglycidyl isocyanurate accounts for 40-99 wt% of the product A.
In the preparation method of the coating curing agent, the organic solvent in the step S1 is any one of dichloroethane, N-dimethylformamide, petroleum ether and toluene.
In the preparation method of the coating curing agent, the base in the step S1 is triethylamine, and the equivalent ratio of the triethylamine to the isocyanuric acid is 2.0-6.0.
In the preparation method of the coating curing agent, the equivalent ratio of chloropropene to isocyanuric acid in the step S1 is 2.5-4.5.
In the preparation method of the coating curing agent, the surfactant in step S2 is any one of tetrabutylammonium bromide, triethylbenzeneammonium chloride, trimethylbenzeneammonium chloride and methyltrioctylammonium chloride, and the weight ratio of the surfactant to the triallyl isocyanurate is 0.03-0.05.
In the preparation method of the coating curing agent, the first catalyst in the step S2 is sodium tungstate, and the weight ratio of the sodium tungstate to the triallyl isocyanurate is 0.05-0.10.
The preparation method of the coating curing agent as described above, step S2The method also comprises the following steps: adding a second catalyst and introducing H 2 And reacting at 20-40 ℃ to obtain a crude product;
the second catalyst is Pd/C.
The preparation method of the coating curing agent comprises the step of preparing the coating curing agent, wherein the coating curing agent comprises triglycidyl isocyanurate with the structural formula (B)
And/or diglycidyl isocyanurates of the formula (D)
The triglycidyl isocyanurate accounts for 40-99 wt% of the product B.
The coating curing agent prepared by the preparation method as described in any one of the above is applied to polyester powder coating.
Compared with the prior art, the invention has the following advantages:
1. the invention provides a preparation method of a coating curing agent, which comprises the steps of adopting isocyanuric acid and chloropropene to react in a mixed liquid of an organic solvent and alkali to synthesize triallyl isocyanurate, oxidizing and synthesizing into triglycidyl isocyanurate under the condition of a catalyst, wherein the triglycidyl isocyanurate is high in purity and basically does not contain Epichlorohydrin (ECH), and the preparation of the curing agent does not use epichlorohydrin with carcinogenicity as a raw material; hydrogen peroxide is used as an oxygen source, and a small amount of harmless water is generated by reaction and is easy to treat; the curing agent has high preparation yield, has advantages in the characteristics of coating film gloss, corrosion resistance, gloss retention, solvent resistance, high temperature resistance and the like, and is obviously a better choice besides TGIC and HAA.
2. The coating curing agent obtained by the preparation method is applied to polyester powder coatings, products contain triglycidyl ester and diglycidyl ester, both of which can react with polyester resin, so that skin allergy does not occur in the production and spraying processes of the powder coatings, and the prepared products do not contain chloride ions and can also be applied to electronic materials.
Detailed Description
In order to better understand the technical features of the present invention, embodiments of the present invention are described in detail below. The following examples are illustrative only and are not to be construed as limiting the invention.
The following examples are provided to facilitate a better understanding of the present invention, but are not intended to limit the invention. The experimental procedures in the following examples are conventional unless otherwise specified.
Example 1
(1) Preparation of triallyl isocyanurate
The reaction vessel, the apparatus, the mechanical stirrer, the condenser and the thermometer were taken out, isocyanuric acid (1.0equiv) was weighed, dichloroethane (6.3equiv) and triethylamine (3.1equiv) were added, and the temperature was raised to 60 ℃. Chloropropene (3.2equiv) was slowly added, the temperature controlled to about 65 ℃ and stirred for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and finishing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, dichloroethane was added, the temperature was lowered to 50 ℃ and washing was carried out with 2 times of water. After separation, the organic layers were combined to give triallyl isocyanurate (purity greater than 98.0 wt%).
(2) Production of the curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), tetrabutyl ammonium bromide and hydrogen peroxide (4.5equiv), wherein the weight ratio of the tetrabutyl ammonium bromide to the product A is 0.03, and the weight ratio of the sodium tungstate to the product A is 0.05. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
sampling and detecting, and adding dichloroethane after the reaction is completed and the content of the starting material is determined to be less than 1%. After layering, collecting the organic layer, cooling, crystallizing, and filtering to obtain a white solid product, wherein the white solid product is a composition of triglycidyl isocyanurate (80 wt%) with a structural formula (B) and propenyl diglycidyl isocyanurate (20 wt%) with a structural formula (C) through chromatographic analysis.
Example 2
(1) Preparation of triallyl isocyanurate
The reaction vessel, the apparatus, the mechanical stirrer, the condenser and the thermometer were taken out, isocyanuric acid (1.0equiv) was weighed, petroleum ether (6.3equiv) and triethylamine (3.1equiv) were added, and the temperature was raised to 60 ℃. Chloropropene (4.5equiv) was slowly added, the temperature controlled to about 65 ℃ and stirred for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and finishing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, petroleum ether was added, the temperature was lowered to 50 ℃ and the mixture was washed with 3 times of water. After separation, the organic layers were combined to give triallyl isocyanurate (purity greater than 98.0 wt%).
(2) Production of curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), triethylbenzene ammonium chloride and hydrogen peroxide (4.5equiv), wherein the weight ratio of the triethylbenzene ammonium chloride to the product A is 0.04, and the weight ratio of the catalyst to the product A is 0.06. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
sampling and detecting, and adding petroleum ether after the reaction is finished and the content of the starting material is determined to be less than 1%. After layering, collecting the organic layer, cooling, crystallizing, and filtering to obtain a white solid product, wherein the white solid product is a composition of triglycidyl isocyanurate (85 wt%) with a structural formula (B) and propenyl diglycidyl isocyanurate (15 wt%) with a structural formula (C) through chromatographic analysis.
Example 3
(1) Preparation of triallyl isocyanurate
The reaction vessel, the apparatus, the mechanical stirrer, the condenser and the thermometer were taken out, isocyanuric acid (1.0equiv) was weighed, toluene (6.3equiv) and triethylamine (3.1equiv) were added, and the temperature was raised to 60 ℃. Chloropropene (3.2equiv) was slowly added, the temperature controlled to about 65 ℃ and stirred for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and finishing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, toluene was added, the temperature was lowered to 50 ℃ and the mixture was washed with 3 times of water. After separation, the organic layers were combined to give triallyl isocyanurate (purity greater than 98.0 wt%).
(2) Production of the curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), benzene trimethyl ammonium chloride and hydrogen peroxide (4.5equiv), wherein the weight ratio of the benzene trimethyl ammonium chloride to the product A is 0.04, and the weight ratio of the catalyst to the product A is 0.07. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
sampling and detecting, and adding toluene after the reaction is completed and the content of the starting material is determined to be less than 1%. After layering, collecting the organic layer, cooling, crystallizing, and filtering to obtain a white solid product, wherein the white solid product is a composition of triglycidyl isocyanurate (90 wt%) with a structural formula (B) and propenyl diglycidyl isocyanurate (10 wt%) with a structural formula (C) through chromatographic analysis.
Example 4
(1) Preparation of triallyl isocyanurate
The reaction vessel, the apparatus, the mechanical stirrer, the condenser tube and the thermometer were taken out, isocyanuric acid (1.0equiv) was weighed, N-dimethylformamide (6.3equiv) and triethylamine (3.1equiv) were added, and the temperature was raised to 60 ℃. Chloropropene (2.5equiv) was slowly added, the temperature controlled to about 65 ℃ and stirred for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and finishing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, N-dimethylformamide was added, the temperature was lowered to 50 ℃ and the mixture was washed with 3 times of water. After separation, the organic layers were combined to give triallyl isocyanurate (purity greater than 98.0 wt%).
(2) Production of curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), a surfactant and hydrogen peroxide (4.5equiv), wherein the weight ratio of the surfactant to the product A is 0.05, and the weight ratio of a catalyst to the product A is 0.08. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
adding a second catalyst Pd/C, introducing hydrogen, and reacting at the temperature of 20 ℃, wherein the reaction formula (III) is as follows:
sampling and detecting, and adding N, N-dimethylformamide after the reaction is finished and the content of the starting material is determined to be less than 1%. After layering, collecting the organic layer, cooling for crystallization, and performing suction filtration to obtain white solid products, wherein the white solid products are subjected to chromatographic analysis to obtain the triglycidyl isocyanurate (95 wt%) with the structural formula (B) and the diglycidyl isocyanurate (5 wt%) with the structural formula (D).
Example 5
(1) Preparation of triallyl isocyanurate
The reaction vessel, the mechanical stirring device, the condenser tube and the thermometer are taken out, the isocyanuric acid (1.0equiv) is weighed, the N, N-dimethylformamide (6.3equiv) and the triethylamine (3.1equiv) are added, and the temperature is raised to 60 ℃. Chloropropene (2.5equiv) is slowly added, the temperature is controlled to about 65 ℃, and stirring is carried out for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and finishing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, N-dimethylformamide was added, the temperature was lowered to 50 ℃ and the mixture was washed with 3 times of water. After separation, the organic layers were combined to give triallyl isocyanurate (purity greater than 98.0 wt%).
(2) Production of the curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), methyl trioctyl ammonium chloride and hydrogen peroxide (4.5equiv), wherein the weight ratio of the methyl trioctyl ammonium chloride to the product A is 0.05, and the weight ratio of a catalyst to the product A is 0.08. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
adding a second catalyst Pd/C, introducing hydrogen, and reacting at the temperature of 20 ℃, wherein the reaction formula (III) is as follows:
sampling and detecting, and adding N, N-dimethylformamide after the reaction is finished and the content of the starting material is determined to be less than 1%. After layering, collecting the organic layer, cooling for crystallization, and performing suction filtration to obtain white solid products, wherein the white solid products are subjected to chromatographic analysis to obtain triglycidyl isocyanurate (94 wt%) having a structural formula (B) and diglycidyl isocyanurate (7 wt%) having a structural formula (D).
Example 6
(1) Preparation of triallyl isocyanurate
The reaction vessel, the apparatus, the mechanical stirrer, the condenser tube and the thermometer were taken out, isocyanuric acid (1.0equiv) was weighed, N-dimethylformamide (6.3equiv) and triethylamine (3.1equiv) were added, and the temperature was raised to 60 ℃. Chloropropene (2.5equiv) was slowly added, the temperature controlled to about 65 ℃ and stirred for 3 hours, the reaction of formula (I) is as follows:
sampling and detecting, and completing the reaction when the content of the starting material is less than 1%. After the solvent was distilled off, N-dimethylformamide was added thereto, and the mixture was cooled to 50 ℃ and washed with 3 times of water. After separation, the organic layers were combined to give triallylisocyanurate (greater than 98.0 wt% purity).
(2) Production of the curing agent
Taking a sodium tungstate aqueous solution, adjusting the pH value to 2.5, adding a product A (1.0equiv), tetrabutyl ammonium bromide and hydrogen peroxide (4.5equiv), wherein the weight ratio of the tetrabutyl ammonium bromide to the product A is 0.05, and the weight ratio of a catalyst to the product A is 0.08. Reacting at 60 ℃ for 18h, wherein the reaction formula (II) is as follows:
adding a second catalyst Pd/C, introducing hydrogen, and reacting at the temperature of 20 ℃, wherein the reaction formula (III) is as follows:
sampling and detecting, and adding N, N-dimethylformamide after the reaction is finished when the content of the starting material is less than 1%. After layering, the organic layer was collected and crystallized by cooling, and white solid products were obtained by suction filtration, and by chromatography, triglycidyl isocyanurate of formula (B) (88 wt%) and diglycidyl isocyanurate of formula (D) (12 wt%) were obtained.
The curing agent prepared in example 1 was compared with commercially available curing agents of various brands, TGIC, for the test standards and specifications, as shown in Table 1 below:
the curing agents containing TGIC obtained in examples 1-6 and the curing agent TGIC commercially available in comparative example were used to prepare common polyester powder coatings to test their performance and effect, the proportion of the curing agent was controlled to be 2-8 wt% of the whole, and the specific formulation is shown in the following Table 2:
table 2: EXAMPLES 1-6 AND COMPARATIVE EXAMPLE TGIC weight component Table of a commercial curing agent (%)
| Components | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Example 6 | Comparative example |
| Polyester resin | 60 | 60 | 60 | 60 | 60 | 60 | 60 |
| Curing agent | 4.5 | 4.5 | 4.5 | 4.5 | 4.5 | 4.5 | 4.5 |
| PE wax | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
| Benzoinum | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 |
| Titanium white powder | 26 | 26 | 26 | 26 | 26 | 26 | 26 |
| Leveling agent | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
The polyester powder coating obtained was subjected to experiments and film properties comparison, and the results are shown in table 3 below:
table 3: comparison of the Performance of commercial curing agent TGIC of examples 1-6 and comparative example
| Test items | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | Examples6 | Comparative example |
| Gloss of coating film | 90.3 | 88.3 | 91.4 | 95.5 | 96.1 | 94.3 | 87.6 |
| Neutral fog salt for 300h | No corrosion | No corrosion | No corrosion | No corrosion | No corrosion | No corrosion | Micro-etching |
| QUV-A500h light retention (%) | 86.3 | 84.1 | 85.1 | 79.8 | 78.5 | 77.2 | 75.8 |
| Leveling/diagonal flow length (cm) | 4.5 | 4.1 | 4.3 | 4.5 | 4.4 | 4 | 3.8 |
| MEK24h solvent treatment loss (%) | 5.86 | 5.6 | 5.73 | 5.83 | 5.88 | 5.83 | 10.25 |
| Temperature resistance test at 220 ℃ for 15min | 0.5 | 0.56 | 0.45 | 0.38 | 0.52 | 0.56 | 0.59 |
Therefore, according to the preparation method of the coating curing agent, epichlorohydrin with carcinogenicity is not used as a raw material in the preparation process; hydrogen peroxide is used as an oxygen source, and a small amount of harmless water is generated by reaction and is easy to treat. The curing agent is prepared in high yield (> 90%), the product contains triglycidyl ester and diglycidyl ester, both of which can react with the polyester resin, and when the diglycidyl ester reaches 20%, the reaction can obtain the highest conversion rate (97%) and the highest yield (92%).
Examples 1 to 3 are compositions containing triglycidyl isocyanurate of formula (B) and propenyl diglycidyl isocyanurate of formula (C) before introduction of hydrogen, compared to examples 4 to 6 which contain triglycidyl isocyanurate of formula (B) and diglycidyl isocyanurate of formula (D) after introduction of hydrogen, since diglycidyl isocyanurate containing unsaturated double bonds is removed by addition of hydrogen, they have excellent gloss of coating film, but their gloss retention is slightly lower than that of examples 1 to 3, but they are substantially equal to or even better than commercially available TGIC, and the prepared products can be applied to electronic materials because they do not contain chloride ions.
The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and principle of the present application should be included in the protection scope of the present application.
Claims (10)
1. A preparation method of a coating curing agent is characterized by comprising the following steps: the method comprises the following steps:
s1, adding isocyanuric acid into a mixed solution containing an organic solvent and alkali, uniformly mixing, adding chloropropene, stirring for 2-4 hours at the temperature of 40-80 ℃, and uniformly mixing to obtain triallyl isocyanurate;
s2, adding an aqueous solution containing a first catalyst, adjusting the pH value, adding the triallyl isocyanurate, the surfactant and hydrogen peroxide obtained in the step S1, uniformly mixing at the temperature of 50-80 ℃, and reacting for 12-24 hours to obtain a crude product;
and S3, adding an extraction solvent into the crude product, layering, collecting an organic layer, cooling, crystallizing, and performing suction filtration to obtain the coating curing agent.
2. The method for preparing a coating curing agent according to claim 1, wherein: the coating curing agent comprises triglycidyl isocyanurate with a structural formula (B)
And/or allyl diglycidylester of isocyanuric acid of the formula (C)
The triglycidyl isocyanurate accounts for 40-99 wt% of the product A.
3. The method for producing a coating curing agent according to claim 1, wherein: the organic solvent in step S1 is any one of dichloroethane, N-dimethylformamide, petroleum ether, and toluene.
4. The method for preparing a coating curing agent according to claim 1, wherein: the base in the step S1 is triethylamine, and the equivalent ratio of the triethylamine to the isocyanuric acid is 2.0-6.0.
5. The method for preparing a coating curing agent according to claim 1, wherein: the equivalent ratio of chloropropene to isocyanuric acid in the step S1 is 2.5-4.5.
6. The method for preparing a coating curing agent according to claim 1, wherein: the surfactant in the step S2 is any one of tetrabutylammonium bromide, triethylphenylammonium chloride, trimethylphenylammonium chloride and methyltrioctylammonium chloride, and the weight ratio of the surfactant to the triallyl isocyanurate is 0.03-0.05.
7. The method for preparing a coating curing agent according to claim 1, wherein: the first catalyst in step S2 is sodium tungstate, and the weight ratio of the sodium tungstate to the triallyl isocyanurate is 0.05-0.10.
8. The method for preparing a coating curing agent according to claim 1, wherein: the step S2 is followed by the following steps: adding a second catalyst and introducing H 2 And reacting at 20-40 ℃ to obtain a crude product;
the second catalyst is Pd/C.
9. The method for preparing a coating curing agent according to claim 8, wherein: the coating curing agent comprises triglycidyl isocyanurate with a structural formula (B)
And/or diglycidyl isocyanurates of the formula (D)
The triglycidyl isocyanurate accounts for 40-99 wt% of the product B.
10. Use of a coating curing agent obtained by the process according to any one of claims 1 to 9 in polyester powder coatings.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603721A (en) * | 2012-02-17 | 2012-07-25 | 湖南大学 | Preparation method of triglycidyl isocyanurate |
| CN107418287A (en) * | 2016-05-23 | 2017-12-01 | 上海药合生化科技有限公司 | Manufacture the method for coating curing agent and its application in coating |
| CN112500399A (en) * | 2020-12-02 | 2021-03-16 | 黄山华惠科技有限公司 | Low-chlorine ECH-residue-free TGIC curing agent and preparation method thereof |
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- 2022-06-14 CN CN202210665755.8A patent/CN114958156A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603721A (en) * | 2012-02-17 | 2012-07-25 | 湖南大学 | Preparation method of triglycidyl isocyanurate |
| CN107418287A (en) * | 2016-05-23 | 2017-12-01 | 上海药合生化科技有限公司 | Manufacture the method for coating curing agent and its application in coating |
| CN112500399A (en) * | 2020-12-02 | 2021-03-16 | 黄山华惠科技有限公司 | Low-chlorine ECH-residue-free TGIC curing agent and preparation method thereof |
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