TWI805415B - Tris(alkoxycarbonylamino)triazine (tact) composition, coating composition comprising the same, and manufacturing method thereof - Google Patents

Abstract

The present invention provides a tris (alkoxycarbonylamino) triazine (TACT) composition, coating composition comprising the same, and manufacturing method thereof. The tris (alkoxycarbonylamino) triazine composition comprises TACT and dibutyl carbonate (DBC); wherein the DBC accounts for the total amount of the composition in 2 to 11 wt % by weight. Through the usage of the coating composition comprising the composition of the present invention, the coating film surface of the coated object can have excellent film surface appearance.

Description

Tris(alkoxycarbonylamino)triazine composition, coating composition containing same and method for producing same

The present invention relates to a tris (alkoxycarbonylamino) triazine (tris (alkoxycarbonylamino) triazine, TACT) composition and a preparation method thereof, the tris (alkoxycarbonylamino) triazine composition can be used as a crosslinking agent, It is especially used as a crosslinking agent in coating compositions.

Tris(alkoxycarbonylamino)triazine (TACT) is a trifunctional melamine-based crosslinker containing reactive carbamate functional groups, which can be used as a crosslinker for water-borne and solvent-borne coatings agent, and because the coating composition containing TACT will not release formaldehyde during the curing process, in addition, it can also make the coating film surface of the coated object have good hardness and chemical resistance, so the coating composition containing TACT has been used Widely used in the field of coatings.

The inventors of this case found after various experiments that the TACT coating composition will be accompanied by the generation of by-product dibutyl carbonate (DBC) during the preparation process; and after research, the inventors also found that the content of the by-product If it is too high or too low, it will have adverse effects on the coating film surface of the coating material coated by the TACT coating composition, such as the formation of pinholes or sags, etc., so that the coating film surface of the coating material will be greatly reduced. aesthetics.

In order to effectively make the by-product DBC in the TACT coating composition not affect the appearance of the coating film surface of the coated object, the inventor of the present case found after many experiments that the DBC content in the coating composition should be controlled at 2 to Between 11 wt%, it can effectively make the coated object coated with the coating composition have an excellent coating film surface appearance.

Therefore, the object of the present invention is to provide a tris (alkoxycarbonylamino) triazine (tris (alkoxycarbonylamino) triazine, TACT) composition, which comprises TACT and dibutyl carbonate (dibutyl carbonate, DBC); wherein, the DBC comprises 2 to 11 wt% of the total weight of the composition.

In one or more embodiments, the DBC comprises 3 to 8 wt% of the total weight of the composition.

(I)， 其中，R ₁-R ₆各自獨立地為H、NR ₇R ₈或脂肪族；R ₇和R ₈獨立地為H、脂肪族、烷氧基或氨基甲酸酯基。 In one or more embodiments, the TACT has the structure of the following general formula (I):

(I), wherein, R ₁ -R ₆ are each independently H, NR ₇ R ₈ or aliphatic; R ₇ and R ₈ are independently H, aliphatic, alkoxy or carbamate.

In one or more embodiments, the R ₂ , R ₃ and R ₅ are H.

In one or more embodiments, the R ₁ , R ₄ and R ₆ are C1-C6 alkyl.

In one or more embodiments, the composition has a solids content of 45 to 60 wt%.

In one or more embodiments, the composition has a pH of 4.5 to 7.0 at 25°C.

In one or more embodiments, the composition has a viscosity of 10 to 30 cps at 25°C.

(II) 與碳酸酯在醇與鹼存在的環境下反應；其中，該通式(II)中之R ₁-R ₆各自獨立地為H、NR ₇R ₈或脂肪族；R ₇和R ₈獨立地為H、脂肪族、烷氧基或氨基甲酸酯基。 Another object of the present invention is to provide a method for preparing a composition, which comprises the following general formula (II)

(II) Reaction with carbonate in the presence of alcohol and base; wherein, R ₁ -R ₆ in the general formula (II) are each independently H, NR ₇ R ₈ or aliphatic; R ₇ and R ₈ are independently H, aliphatic, alkoxy, or carbamate.

In one or more embodiments, the preparation method further comprises, additionally adding DBC to make it account for 2 to 11 wt% of the total weight of the composition.

In one or more embodiments, the carbonate is dimethyl carbonate.

In one and more embodiments, the base is an alkali metal alkoxide or an alkaline earth metal alkoxide.

In one or more embodiments, the alkali metal alkoxide is sodium t-butoxide or sodium methoxide.

Another object of the present invention is to provide a coating composition comprising the aforementioned TACT composition as a crosslinking agent.

The effect of the present invention is that, through the use of the tris(alkoxycarbonylamino)triazine composition of the present invention, the object to be coated can have an excellent coating film surface appearance.

The following embodiments should not be considered as unduly limiting the present invention. Those skilled in the art to which the present invention pertains can make modifications and changes to the embodiments discussed herein without departing from the spirit or scope of the present invention, and such modifications and changes still belong to the scope of the present invention.

"A" and "an" mentioned herein represent one or more than one (ie at least one) of the grammatical object herein.

The object of the present invention is to provide a kind of three (alkoxycarbonyl amino) triazine (tris (alkoxycarbonylamino) triazine, TACT) composition, it comprises TACT and dibutyl carbonate (dibutyl carbonate, DBC); Wherein, this DBC occupies the 2 to 11 wt % of the total weight of the composition.

(I)， 其中，R ₁-R ₆各自獨立地為H、NR ₇R ₈或脂肪族；R ₇和R ₈獨立地為H、脂肪族、烷氧基或氨基甲酸酯基。 The "tris (alkoxycarbonylamino) triazine (tris (alkoxycarbonylamino) triazine, TACT)" described herein refers to dibutyl carbonate (dibutyl carbonate) comprising TACT and accounting for 2 to 11 wt% of the total weight of the composition. carbonate, DBC), and the TACT has the structure of the following general formula (I):

(I), wherein, R ₁ -R ₆ are each independently H, NR ₇ R ₈ or aliphatic; R ₇ and R ₈ are independently H, aliphatic, alkoxy or carbamate.

The aforementioned "aliphatic" refers to an organic compound or free radical with a straight chain, branched chain or closed ring structure, which may contain one or more saturated carbon bonds or unsaturated carbon bonds, and has 1 to 24 carbon atoms, specifically for example but Not limited to: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

In one or more embodiments, the R ₁ , R ₄ and R ₆ are preferably but not limited to C1-C6 alkyl, and the aforementioned "alkyl" refers to a single bond (alkyl) and a double bond (alkene radical) straight-chain or branched saturated aliphatic radicals having 1 to 12 carbon atoms, for example: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms , in the present invention is preferably 1 to 6 carbon atoms; the alkyl can specifically be but not limited to: methyl, ethyl, 1-propyl, isopropyl, 1-butyl, 2-butyl , isobutyl, tert-butyl, pentyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, pentyl, isopentyl, hexyl, 4-methylpentyl, 1-methyl Pentyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3 -Dimethylbutyl, 1,2,2-trimethylpropyl, 1,1,2-trimethylpropyl, 2-ethylpentyl, 3-ethylpentyl, hexyl, 1-methyl Dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 4,4-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl Pentyl, 4,4-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 1,2,3-tri Methylbutyl, 1,1,2-trimethylbutyl, 1,1,3-trimethylbutyl, 5-methylheptyl, 1-methylheptyl, octyl, nonyl, decyl base, undecyl or dodecyl, etc.

In one or more embodiments, the R ₂ , R ₃ and R ₅ are H.

In one or more embodiments, the DBC accounts for 2 to 11 wt% of the total weight of the TACT composition, specifically for example but not limited to the range between any two of the following values, for example: 2 wt%, 3 wt% %, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt% or 11 wt%; preferably 3 to 8 wt% in the present invention.

In one or more embodiments, the solid content of the TACT composition is 45 to 60 wt%, and the measurement method of the solid content is carried out with reference to DIN EN ISO 3251, that is, the TACT composition is baked at 105°C After baking for 2 hours, the remaining part of the TACT composition accounts for the mass percentage of the original total amount. The solid content of the TACT composition is specifically, but not limited to, the range between any two of the following values, for example: 45 wt%, 46 wt%, 47 wt%, 48 wt%, 49 wt%, 50 wt%, 51 wt% %, 52 wt%, 53 wt%, 54 wt%, 55 wt%, 56 wt%, 57 wt%, 58 wt%, 59 wt% or 60 wt%.

The "pH value" mentioned herein refers to the measurement result of the TACT composition at 25°C. The inventors of the present case found that if the pH value of the TACT composition measured at 25°C is too high or too low, the composition may be degraded, so it is preferable to measure the TACT composition at 25°C The measured pH value is controlled within a certain range. In one or more embodiments, the TACT composition has a pH value of 4.5 to 7.0 at 25°C, for example but not limited to the range between any two of the following values, for example: 4.5, 4.75, 5.0, 5.25, 5.5, 5.75, 6.0, 6.25, 6.5, 6.75, or 7.0.

The "viscosity" mentioned herein refers to the measurement result of the TACT composition at 25°C. The inventors of the present case found that if the viscosity of the TACT composition measured at 25°C is too high or too low, it will be unfavorable for the spraying of the coating composition containing the TACT composition, so it is better to use the TACT composition The viscosity measured at 25°C is controlled within a certain range. In one or more embodiments, the viscosity of the TACT composition at 25°C is 10 to 30 cps, specifically for example but not limited to the range between any two of the following values, for example: 10 cps, 12 cps, 14 cps , 16 cps, 18 cps, 20 cps, 22 cps, 24 cps, 26 cps, 28 cps, or 30 cps.

(II) 與碳酸酯在醇與鹼存在的環境下反應；其中，該通式(II)中之R ₁-R ₆各自獨立地為H、NR ₇R ₈或脂肪族；R ₇和R ₈獨立地為H、脂肪族、烷氧基或氨基甲酸酯基。 Another object of the present invention is to provide a method for preparing a composition, which comprises the following general formula (II)

(II) Reaction with carbonate in the presence of alcohol and base; wherein, R ₁ -R ₆ in the general formula (II) are each independently H, NR ₇ R ₈ or aliphatic; R ₇ and R ₈ are independently H, aliphatic, alkoxy, or carbamate.

In one or more embodiments, the carbonate is dimethyl carbonate.

In one or more embodiments, the alcohol is an alkanol, such as but not limited to methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, tert-butanol, pentanol, Isoamyl alcohol, neopentyl alcohol, tert-amyl alcohol, hexanol, 2-methylpentanol, heptanol, octanol, 2-ethylhexanol, isooctyl alcohol, nonanol, isononanol, decanol, iso Decyl Alcohol, Undecyl Alcohol, Dodecyl Alcohol, Tridecyl Alcohol, Isotridecyl Alcohol, 2-Methoxyethanol, 2-Ethoxyethanol, 2-Propoxyethanol, 2-Butoxyethanol Ethanol, 2- or 3-methoxypropanol, 2- or 3-ethoxypropanol, 2- or 3-propoxypropanol, 2- or 4-methoxybutanol, 2- or 4 - Ethoxybutanol, 3, 6-dioxaheptanol, 3, 6-dioxoctanol, 3, 7-dioxoctanol, 4, 7-dioxoctanol, 2- or 3-butoxypropanol or 2- or 4-butoxybutanol, etc. Moreover, the alcohols used in the present invention can be used alone or in combination. If they are used in combination, the components and proportions of each alcohol composition in the mixture can be adjusted arbitrarily according to the usage situation.

In one or more embodiments, the base is an alkali metal alkoxide or an alkaline earth metal alkoxide, such as but not limited to sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium tert-butoxide, potassium methoxide, Potassium ethoxide, potassium tert-butoxide, magnesium potassium alkoxide or magnesium ethoxide; in a preferred embodiment, the alkali metal alkoxide is sodium tert-butoxide or sodium methoxide.

In order to effectively control the generation amount of the by-product DBC in the preparation process of the TACT composition, the process parameters of the coating composition can be adjusted, especially for sodium methoxide (Sodium methoxide, SM) or sodium tert-butoxide (Sodium tert-butoxide , STB) to adjust the amount of addition, such as when the content of DBC is too much, the amount of DBC can be reduced by increasing the amount of SM or reducing the amount of STB added; on the contrary, when the content of DBC is insufficient, you can use Reduce the amount of SM or increase the amount of STB, thereby increasing the amount of DBC; in addition, it can also be adjusted by regulating the amount of carbonate added. When the amount of carbonate added is higher, the amount of DBC in the composition can be increased. content increased.

The inventors of the present case further found that, without being limited to a specific theory, in addition to controlling the amount of by-product DBC produced in the preparation process of the TACT composition through the aforementioned methods, especially by adjusting the amount of carbonate, SM or STB added ; It is also possible to make DBC account for 2 to 11 wt% of the total weight of the composition by additionally adding DBC, so that the coated object has an excellent coating film surface appearance.

Therefore, during the preparation of the TACT composition, an additional appropriate amount of DBC may be added to make it account for 2 to 11 wt% of the total weight of the composition.

Another object of the present invention is to provide a coating composition comprising the aforementioned TACT composition as a crosslinking agent.

In one or more embodiments, the coating composition may further comprise a polymeric resin such as, but not limited to, functionalized or unfunctionalized acrylic, styrene acrylic, vinyl acrylic, polyester, polyether , polyurethane or alkyd resin polymers, etc.

In one or more embodiments, the coating composition may further include a solvent to improve the solubility, dispersibility and/or storage stability of each component in the coating composition. Aforesaid solvent can be water or organic solvent, and this organic solvent can be but not limited to glycol ether, and specific example is butyl glycol, butyl diglycol, ethoxypropanol, dipropylene glycol dimethyl ether, dipropylene glycol monomethyl Ether or ethylene glycol dimethyl ether, etc.; glycol ether esters, such as ethylene glycol acetate, butyl glycol acetate, butyl diglycol acetate or methoxypropyl acetate etc.; diols, such as propylene glycol and its oligomers, etc.; esters, such as butyl acetate, isobutyl acetate or pentyl acetate, etc.; ketones, such as methyl ethyl ketone, methyl isobutyl Ketones, diisobutyl ketone, cyclohexanone or isophorone, etc.; alcohols, such as methanol, ethanol, (iso)propanol, butanol or hexanol, etc.; N-alkylpyrrolidones, such as N-ethyl base pyrrolidone, etc.; aromatic hydrocarbons, such as toluene or aliphatic hydrocarbons, etc.; paint solvent (S100), etc.; or a combination of any of the aforementioned solvents.

In one or more embodiments, the coating composition may further include catalysts, defoamers, light stabilizers, pigments, dispersants, rheology modifiers, flow agents, fillers, etc. as additives.

The aforementioned catalyst may be, but not limited to, an acid catalyst, a base catalyst, or a salt catalyst. The aforementioned defoamer may be, but not limited to, polyether defoamer, silicone defoamer, or mineral oil defoamer. The light stabilizer mentioned above can be but not limited to UV shielding agent (UV protective powder), ultraviolet absorber (UV absorber, UVA), inhibitor (quencher) or hindered amine light stabilizer (hindered amine light stabilizer, HALS). The aforementioned dispersant can be but not limited to anionic wetting and dispersing agent, cationic wetting and dispersing agent, nonionic wetting and dispersing agent, zwitterionic wetting and dispersing agent, electrically neutral wetting and dispersing agent, polymer hyperdispersant or controllable Free radical hyperdispersant, etc. The aforementioned rheology modifiers can be but not limited to inorganic rheology additives or organic rheology additives, such as vinylpyrrolidone copolymer, aluminum magnesium silicate crystalline hydrate, non-associative thickener, associative thickener, etc. Thickener or non-ionic associative thickener, etc. The aforementioned filler may be but not limited to silicon dioxide. Example

Hereinafter, the present invention will be further described in detail with examples. However, it should be understood that these examples are only used to help understanding of the present invention rather than limiting the scope of the present invention.

[Sample Preparation]

Example 1

36 g of melamine (melamine, Mel) and 99.9 g of dimethyl carbonate (dimethyl carbonate, DMC) were dropped into 60 g of n-butyl alcohol (n-butyl alcohol, NBA) to form a reaction mixture; then in the reaction 625 g of n-butanol (NBA) solution containing 20% sodium tert-butoxide (sodium tert-butoxide, STB) was added to the mixture; Reaction mixture is cooled to room temperature; Then in this reaction mixture, add the 25% sulfuric acid aqueous solution of 300 g, and stir until this reaction mixture is homogeneous phase; After standing this reaction mixture, this reaction mixture lower floor water is discharged; Then with After the remaining reaction mixture was stirred and washed with water; then the reaction mixture was left to stand and the lower layer of water was discharged; then the reaction mixture was distilled to remove excess water and NBA after decompression and heating; then add NBA to dilute the reaction mixture; Filter paper to filter the solid residue in the reaction mixture, and finally obtain the TACT composition sample of Example 1, then perform DBC content detection.

Example 2

36 g of Mel and 88.8 g of DMC were dropped into 60 g of NBA to form a reaction mixture; then 625 g of NBA solutions containing 20% STB were added to the reaction mixture; the reaction mixture was warmed up to 85 ° C, and at After stirring under the aforementioned environment for 180 minutes, the reaction mixture was cooled to room temperature; then, 300 g of 25% sulfuric acid aqueous solution was added in the reaction mixture, and stirred until the reaction mixture was a homogeneous phase; after the reaction mixture was left standstill, the The water in the lower layer of the reaction mixture is discharged; then the remaining reaction mixture is stirred and washed with water; then the reaction mixture is allowed to stand and the water in the lower layer is discharged; then the reaction mixture is distilled to remove excess water and NBA after decompression and heating; Then add NBA to dilute the reaction mixture; then filter the solid residue in the reaction mixture with filter paper, and finally obtain the TACT composition sample of Example 2, then carry out DBC content detection.

Example 3

Take 180 g of the TACT composition sample of Example 2, put in 2.62 g of dibutyl carbonate (dibutyl carbonate, DBC) and stir evenly, and finally obtain the TACT composition sample of Example 3, then perform DBC content detection.

Example 4

Take 180 g of the TACT composition sample of Example 2, put in 10.57 g of DBC and stir evenly, and finally obtain the TACT composition sample of Example 4, then perform DBC content detection.

Example 5

Take 180 g of the TACT composition sample of Example 1, put in 12.45 g of DBC and stir evenly, and finally obtain the TACT composition sample of Example 5, then perform DBC content detection.

comparative example 1

The Mel of 36 g and the DMC of 95 g are dropped in the NBA of 60 g, form a reaction mixture; Then in this reaction mixture, add the NBA solution that contains 14.7% sodium methoxide (sodium methoxide, SM) 586 g; The reaction mixture Be warming up to 85°C, and after stirring for 180 minutes under the aforementioned environment, the reaction mixture is cooled to room temperature; then, 345 g of 25% sulfuric acid aqueous solution is added to the reaction mixture, and stirred until the reaction mixture is a homogeneous phase; After placing the reaction mixture, discharge the water in the lower layer of the reaction mixture; then stir and wash the remaining reaction mixture with water; then let the reaction mixture stand and discharge the water in the lower layer; then reduce the pressure and increase the temperature to distill off the reaction mixture After excess moisture and NBA; then add NBA to dilute the reaction mixture; then filter the solid residue in the reaction mixture with filter paper, and finally obtain the TACT composition sample of Comparative Example 1, then carry out DBC content detection.

comparative example 2

36 g of Mel and 111 g of DMC were dropped into 60 g of NBA to form a reaction mixture; then 625 g of NBA solutions containing 20% STB were added to the reaction mixture; the reaction mixture was heated to 85 ° C, and After stirring under the aforementioned environment for 180 minutes, the reaction mixture was cooled to room temperature; then, 300 g of 25% sulfuric acid aqueous solution was added in the reaction mixture, and stirred until the reaction mixture was a homogeneous phase; after the reaction mixture was left standstill, the The water in the lower layer of the reaction mixture is discharged; then the remaining reaction mixture is stirred and washed with water; then the reaction mixture is allowed to stand and the water in the lower layer is discharged; then the reaction mixture is distilled to remove excess water and NBA after decompression and heating; Then add NBA to dilute the reaction mixture; then filter the solid residue in the reaction mixture with filter paper, and finally obtain the TACT composition sample of Comparative Example 2, then carry out DBC content detection.

comparative example 3

29 g of Mel and 82.9 g of DMC were dropped into 972 g of NBA to form a reaction mixture; then 87 g of 14.7% SM solid powder was added to the reaction mixture; the reaction mixture was warmed up to 78° C., and After stirring for 180 minutes under ambient conditions, the reaction mixture was cooled to room temperature; then, 338.2 g of 30% nitric acid aqueous solution was added in the reaction mixture, and stirred until the reaction mixture was a homogeneous phase; after the reaction mixture was allowed to stand, the The water in the lower layer of the reaction mixture is discharged; then the remaining reaction mixture is stirred and washed with water; then the reaction mixture is allowed to stand and the water in the lower layer is discharged; then the reaction mixture is distilled to remove excess water and NBA after decompression and heating; Add NBA to dilute the reaction mixture; then filter the solid residue in the reaction mixture with filter paper, and finally obtain the TACT composition sample of Comparative Example 3, then carry out DBC content detection.

[by-product DBC detection]

To detect the by-product DBC content in each sample, an autosampler AOC-20i/AOC-20s (manufactured by SHIMADZU Corporation) was used to perform gas chromatography (Gas Chromagtography) with a flame ionization detector (FID). ) for detection, the detection conditions are set as follows: Carrier gas: Nitrogen Gas flow rate: 3.0 ml/min Gas volume: 1 ml Injection inlet temperature: 150℃ Detector temperature: 200℃ Column: ZB-1 (1.50 mm, 0.53 mm x 30 m) The temperature gradient curve of the detector: After injecting the sample, first keep the oven temperature at 40°C for 4 minutes, then raise the oven temperature to 68°C at a heating rate of 3°C/min, and then increase the temperature at a heating rate of 7°C/min The oven temperature was raised to 150°C for 5 minutes. Total run time: 30.05 minutes

According to the results of GC analysis, the by-product DBC of each sample was washed out at the 24th to 26th minute of residence time, and the DBC content of each sample was further calculated through the calibration curve.

[Calculation of by-product DBC content]

1. DBC calibration curve drawing

Add 500 ppm, 1500 ppm and 2500 ppm DBC standard into tetrahydrofuran (THF) solution to prepare three different DBC standard solutions respectively, then measure the area value of these DBC standard solutions according to the aforementioned GC measurement conditions, and then according to The calculated area value and its corresponding DBC concentration value draw the DBC calibration line shown in Figure 1.

2. Calculation method of DBC content

The sample to be tested is diluted 50 times with THF solution, and the diluted samples are measured under the aforementioned GC measurement conditions, and then the area of the DBC peak at the position of the 24th to 26th minute of the retention time of the samples is calculated value, and then convert the DBC content of each sample through the DBC calibration curve drawn above.

[Appearance test of coating film surface]

Prepare each sample into a coating composition according to the formula in Table 1 below, dilute it to the construction viscosity of Ford No. The coated base plates were baked at 140°C for 30 minutes to form a base plate with a coating layer thickness of 22 to 30 μm, and then the appearance of the coating film surface was observed.

Table 1 raw material Weight (wt%) Acrylic 63 acid catalyst 1 Butylated Amino Resin 12.8 Examples or samples of comparative examples 9 paint solvent 10.65 Butanol 3.55

[Experimental Results]

Please refer to Table 2. Table 2 is the physical properties and process parameters of the TACT composition samples of Examples 1 to 5 and Comparative Examples 1 to 3, and the coating film surface appearance test of the coating composition prepared from these samples. Result; Please also refer to FIG. 2 , which is a photo of the coating test results of Examples 1 to 5 and Comparative Examples 1 to 3.

Table 2 Example 1 Example 2 Example 3 Example 4 Example 5 Comparative example 1 Comparative example 2 Comparative example 3 Process conditions Mel (g) 36 36 36 36 36 36 36 29 DMC (g) 99.9 88.8 88.8 88.8 99.9 95 111 82.9 NBA (g) 60 60 60 60 60 60 60 972 20%STB (g) 625 625 625 625 625 - 625 - 14.7% SM (g) - - - - - 586 - 87 25% _{H2SO4 (} g) 300 300 300 300 300 345 300 - 30%HNO ₄ (g) - - - - - - - 338.2 Additional DBC content (g) - - 2.62 10.57 12.45 - - - physical properties Final DBC content (%) 4.83 2.26 3.66 7.68 10.98 1.27 12 13.29 Solid content (wt%) 51.6 51.4 49.4 48.1 48.9 51.1 51.8 48.2 pH (25°C) 6.17 6.02 6.82 6.75 6.85 6.85 6.2 6.62 Vis (cps/25℃) 26.22 24.97 22.65 18.37 21.25 24.45 26.8 18.37 Appearance evaluation of coating film surface normal normal normal normal normal pinhole Sagging Sagging

In the above Table 2, the appearance evaluation of the paint film surface is "normal" means that the paint film surface does not have any pinholes or sags. Therefore, it can be seen from Examples 1 to 5 in Table 2 that controlling the DBC in the TACT composition Accounting for 2 to 11 wt% of the total weight of the composition, after the coating composition comprising the TACT composition is coated on the object to be coated, the object to be coated can present an excellent coating film surface appearance; Examples 1 to 3 accounted for 2 to 11 wt% of the total weight of the composition because DBC in its TACT composition was not controlled, resulting in the coating film surface of the coated object coated with the coating composition comprising the TACT composition of Comparative Example 1 There are pinholes, and the paint film surfaces of Comparative Examples 2 and 3 show the phenomenon of sagging.

In summary, through the tris (alkoxycarbonylamino) triazine (tris (alkoxycarbonylamino) triazine, TACT) composition of the present invention, it comprises TACT and dibutyl carbonate accounting for 2 to 11 wt % of the total weight of the composition The use of (dibutyl carbonate, DBC) can make the coating composition containing it coated, so that the coated object will not produce pinholes or sagging, so as to present an excellent coating film surface appearance.

Herein, all ranges provided are intended to include each specific range within the given range as well as combinations of subranges between the given ranges. Additionally, unless otherwise stated, all ranges provided herein include the endpoints of the stated range. Thus, the range 1-5 specifically includes 1, 2, 3, 4, and 5, and sub-ranges such as 2-5, 3-5, 2-3, 2-4, 1-4, and so on.

All publications and patent applications cited in this specification are herein incorporated by reference, and for any and all purposes, each individual publication or patent application is specifically and individually indicated to be incorporated by reference. In the event of any inconsistency between this document and any publication or patent application incorporated herein by reference, this document controls.

The terms "including", "having" and "comprising" are used herein in an open, non-limiting sense. The terms "a" and "the" should be understood to cover both the plural and the singular. The term "one or more" means "at least one" and thus may include a single feature or a mixture/combination of features.

Except in the working examples or where otherwise indicated, all numbers expressing ingredients and/or reaction conditions are in all instances modified by the term "about", meaning within ± 5% of the indicated number. As used herein, the term "substantially free" or "substantially free" means less than about 2% of a specified characteristic. All elements or features affirmatively stated herein may be negatively excluded from the scope of claims.

none.

Fig. 1 is the DBC calibration curve used when the present invention calculates the DBC content in the sample.

Fig. 2 is the photos of the coating test results of Examples 1 to 5 and Comparative Examples 1 to 3.

none.

Claims (13)

A three (alkoxycarbonylamino) triazine (tris (alkoxycarbonylamino) triazine, TACT) composition, which comprises TACT and dibutyl carbonate (dibutyl carbonate, DBC); wherein, the DBC accounts for 2% of the total weight of the composition to 11wt%. The composition as claimed in item 1, wherein the DBC accounts for 3 to 8wt% of the total weight of the composition. The composition as claimed in item 1, wherein the TACT has the structure of the following general formula (I):

Wherein, R ₁ -R ₆ are each independently H, NR ₇ R ₈ , alkyl, cycloalkyl, alkenyl or alkynyl; R ₇ and R ₈ are independently H, alkyl, cycloalkyl, alkenyl , alkynyl, alkoxy or carbamate groups. The composition according to claim 3, wherein R ₂ , R ₃ and R ₅ are H. The composition according to claim 4, wherein the R ₁ , R ₄ and R ₆ are C1-C6 alkyl groups. The composition according to any one of claims 1 to 5, wherein the solid content of the composition is 45 to 60wt%. The composition according to any one of claims 1 to 5, wherein the composition has a pH value of 4.5 to 7.0 at 25°C. The composition according to any one of claims 1 to 5, wherein the composition has a viscosity of 10 to 30 cps at 25°C. A method for preparing the composition of any one of claims 1 to 8, which comprises the following general formula (II)

React with carbonate in the presence of alcohol and alkali, and control DBC to account for 2 to 11wt% of the total weight of the composition; wherein, R ₁ -R ₆ in the general formula (II) are each independently H, NR ₇ R ₈ , alkyl, cycloalkyl, alkenyl or alkynyl; R ₇ and R ₈ are independently H, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy or carbamate. The method of claim 9, wherein the carbonate is dimethyl carbonate. The method of claim 9, wherein the alkali is an alkali metal alkoxide or an alkaline earth metal alkoxide. The method of claim 11, wherein the alkali metal alkoxide is sodium tert-butoxide or sodium methoxide. A coating composition comprising the TACT composition according to any one of claims 1 to 8 as a crosslinking agent.

Images