CN115109454A

CN115109454A - Tris (alkoxycarbonylamino) triazine compositions, coating compositions containing the same, and methods of making the same

Info

Publication number: CN115109454A
Application number: CN202210719433.7A
Authority: CN
Inventors: 蔡彦廷; 赖一江
Original assignee: Chang Chun Plastics Co Ltd
Current assignee: Chang Chun Plastics Co Ltd
Priority date: 2022-06-23
Filing date: 2022-06-23
Publication date: 2022-09-27

Abstract

The invention provides a tri (alkoxycarbonylamino) triazine (TACT) composition, a coating composition containing the same and a preparation method thereof, wherein the tri (alkoxycarbonylamino) triazine composition contains TACT and dibutyl carbonate (DBC); wherein the DBC accounts for 2 to 11 weight percent of the total weight of the composition. By using the coating composition comprising the composition of the present invention, the coating film surface of the coated object can be provided with excellent film surface appearance.

Description

Tris (alkoxycarbonylamino) triazine compositions, coating compositions containing the same, and methods of making the same

Technical Field

The present invention relates to tris (alkoxycarbonylamino) triazine (TACT) compositions useful as crosslinkers, particularly for use as crosslinkers in coating compositions, and to methods of making the same.

Background

Tris (alkoxycarbonylamino) triazine (TACT), which is a trifunctional melamine-based crosslinker containing reactive carbamate functional groups, is used as a crosslinker for water-borne and solvent-borne coatings, and because the coating composition containing TACT does not release formaldehyde during curing and the coating film side of the coated object has good hardness and chemical resistance, the coating composition containing TACT has been widely used in the coating field.

Disclosure of Invention

After various experiments, the inventors of the present application found that a TACT coating composition is accompanied by the generation of dibutyl carbonate (DBC) as a byproduct in the preparation process; as a result of the research, the inventors further found that too high or too low content of the by-product may adversely affect the coating film surface of the object coated by the TACT coating composition, such as pinhole formation or sagging, so as to significantly reduce the aesthetic property of the coating film surface of the object.

After many experiments, the inventor of the present application finds that controlling the DBC content in the coating composition to be between 2 and 11 wt% can effectively provide excellent film surface appearance of the coating on the coated object coated by the coating composition.

Accordingly, it is an object of the present invention to provide a tris (alkoxycarbonylamino) triazine (TACT) composition comprising TACT and dibutyl carbonate (DBC); wherein the DBC accounts for 2 to 11 weight percent 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.

In one or more embodiments, the TACT has the structure of the following general formula (I):

wherein R is ₁ -R ₆ Each independently is H, NR ₇ R ₈ Or aliphatic; r ₇ And R ₈ Independently H, aliphatic, alkoxy or carbamate.

In one or more embodiments, the R ₂ 、R ₃ And R ₅ Is H.

In one or more embodiments, the R ₁ 、R ₄ And R ₆ Is 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 ℃.

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

Another object of the present invention is to provide a process for preparing a composition, which comprises reacting a compound of the following formula (II)

Reacting with a carbonate in the presence of an alcohol and a base; wherein R in the general formula (II) ₁ -R ₆ Each independently is H, NR ₇ R ₈ Or aliphatic; r is ₇ And R ₈ Independently H, aliphatic, alkoxy or carbamate.

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

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

In one or 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 tert-butoxide or sodium methoxide.

It is another object of the present invention to provide a coating composition comprising a TACT composition as described above as a cross-linker.

The invention has the effect that the application object can have excellent coating film surface appearance by using the tri (alkoxycarbonylamino) triazine composition.

Drawings

FIG. 1 is a DBC calibration curve used in the calculation of DBC content in a sample according to the present invention.

FIG. 2 is a photograph showing the results of paint tests of examples 1 to 5 and comparative examples 1 to 3.

Detailed Description

The following embodiments should not be construed to unduly limit the invention. One of ordinary skill in the art may effect modifications and variations to the embodiments discussed herein without departing from the spirit or scope of the present invention, and such modifications and variations are within the scope of the present invention.

The terms "a" and "an" as used herein mean one or more than one (i.e., at least one) of the grammatical object of the article.

The invention aims to provide a tri (alkoxycarbonylamino) triazine (tris (alkoxy carbonyl amino) triazine, TACT) composition, which comprises TACT and dibutyl carbonate (DBC); wherein the DBC accounts for 2 to 11 weight percent of the total weight of the composition.

"tris (alkoxycarbonylamino) triazine composition (TACT)" as used herein refers to a composition comprising TACT and 2 to 11 wt% of dibutyl carbonate (DBC) based on the total weight of the composition, wherein the TACT has the following structure of the general formula (I):

The "aliphatic group" refers to an organic compound or a radical having a linear, branched or closed ring structure, which may include one or more saturated or unsaturated carbon bonds, and has 1 to 24 carbon atoms, such as 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 Preferably, but not limited to, C1-C6 alkyl, and the aforementioned "alkyl" means a straight or branched chain saturated aliphatic group containing a single bond (alkyl) and a double bond (alkenyl) and having 1 to 12Carbon atoms, for example: 1. 2,3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, preferably 1 to 6 carbon atoms in the present invention; the alkyl group may be in particular, but not limited to: methyl group, ethyl group, 1-propyl group, isopropyl group, 1-butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, 1, 2-dimethylpropyl group, 1-dimethylpropyl group, pentyl group, isopentyl group, hexyl group, 4-methylpentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 2, 2-dimethylbutyl group, 3-dimethylbutyl group, 1, 2-dimethylbutyl group, 1, 3-dimethylbutyl group, 1,2, 2-trimethylpropyl group, 1, 2-trimethylpropyl group, 2-ethylpentyl group, 3-ethylpentyl group, hexyl group, 1-methylhexyl group, 2, 2-dimethylpentyl group, 3-dimethylpentyl group, 4-dimethylpentyl group, 1, 2-dimethylpentyl group, 1, 3-dimethylpentyl group, 4-dimethylpentyl group, 1, 2-dimethylpentyl group, 1, 3-dimethylpentyl group, 1, 4-dimethylpentyl group, 1,2, 3-trimethylbutyl group, 1, 2-trimethylbutyl group, 1, 3-trimethylbutyl group, 5-methylheptyl group, 1-methylheptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group or the like.

In one or more embodiments, the R ₂ 、R ₃ And R ₅ Is H.

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

In one or more embodiments, the TACT composition has a solids content of 45 to 60 wt%, and the solids content is measured with reference to DIN EN ISO 3251, i.e., the percentage by mass of the remainder of the TACT composition based on its original total amount after baking the TACT composition at 105 ℃ for 2 hours. Specific examples of the solid content of the TACT composition include, but are not limited to, a 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%.

As used herein, "pH" refers to the measurement of the TACT composition at 25 ℃. The inventors have found that if the pH of the TACT composition measured at 25 ℃ is too high or too low, the composition may degrade, and therefore it is preferable to control the pH of the TACT composition measured at 25 ℃ within a certain range. In one or more embodiments, the TACT composition has a pH at 25 ℃ of 4.5 to 7.0, specifically such as but not limited to a 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.

As used herein, "viscosity" refers to the measurement of the TACT composition at 25 ℃. The inventors have found that too high or too low a viscosity of the TACT composition measured at 25 ℃ is detrimental to the spraying of a coating composition comprising the TACT composition, and therefore it is preferred to control the viscosity of the TACT composition measured at 25 ℃ within a certain range. In one or more embodiments, the TACT composition has a viscosity of 10 to 30cps at 25 ℃, such as, but not limited to, a range between any two of the following values, for example: 10cps, 12cps, 14cps, 16cps, 18cps, 20cps, 22cps, 24cps, 26cps, 28cps or 30 cps.

Another object of the present invention is to provide a process for the preparation of a composition comprising reacting a compound of the following formula (II)

Reacting with carbonate in the presence of alcohol and alkali; wherein R in the general formula (II) ₁ -R ₆ Each independently is H, NR ₇ R ₈ Or aliphatic; r ₇ And R ₈ 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, isopentanol, neopentyl alcohol, tert-pentanol, hexanol, 2-methylpentanol, heptanol, octanol, 2-ethylhexanol, isooctanol, nonanol, isononanol, decanol, isodecanol, undecanol, dodecanol, tridecanol, isotridecanol, 2-methoxyethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-butoxyethanol, 2-or 3-methoxypropanol, 2-or 3-ethoxypropanol, 2-or 3-propoxypropanol, 2-or 4-methoxybutanol, 2-or 4-ethoxybutanol, 3, 6-dioxaheptanol, a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable salt thereof, 3. 6-dioxaoctanol, 3, 7-dioxaoctanol, 4, 7-dioxaoctanol, 2-or 3-butoxypropanol, 2-or 4-butoxybutanol, or the like. And the alcohols used in the present invention may be used alone or in admixture, and if used in admixture, the components and proportions of the respective alcohol compositions in the admixture may be arbitrarily adjusted depending on the use cases.

In one or more embodiments, the base is an alkali metal alkoxide or alkaline earth metal alkoxide, such as, but not limited to, sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium t-butoxide, potassium methoxide, potassium ethoxide, potassium t-butoxide, magnesium potassium alkoxide, or magnesium ethoxide, and the like; 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 byproduct DBC in the preparation process of the TACT composition, the process parameters of the coating composition may be adjusted, especially the addition amount of Sodium Methoxide (SM) or Sodium tert-butoxide (STB), for example, when the content of DBC is too large, the generation amount of DBC may be reduced by increasing SM or reducing the addition amount of STB; on the contrary, when the content of DBC is insufficient, the amount of DBC generated can be increased by reducing SM or increasing the addition amount of STB; the amount of the carbonate added may be adjusted by controlling the amount of the carbonate added, and the DBC content of the composition may be increased as the amount of the carbonate added is higher.

The present inventors have further found that, without being bound to a particular theory, in addition to controlling the amount of DBC produced as a by-product in the preparation of a TACT composition in the aforementioned manner, particularly by adjusting the amount of carbonate, SM or STB added; DBC can also be added to make DBC account for 2-11 wt% of the total weight of the composition, so that the coated object has excellent coating film surface appearance.

Therefore, during the preparation of the TACT composition, DBC may be additionally added in an amount of 2 to 11 wt% based on the total weight of the composition.

In one or more embodiments, the coating composition further can include a polymeric resin, such as, but not limited to, an acrylic, styrene acrylic, vinyl acrylic, polyester, polyether, polyurethane, or alkyd polymer, and the like, which can be functionalized or unfunctionalized.

In one or more embodiments, the coating composition further can include a solvent to enhance the solubility, dispersibility, and/or storage stability of the ingredients in the coating composition. The aforementioned solvent may be water or an organic solvent, which may be, but not limited to, glycol ethers, such as butyl glycol, butyl diglycol, ethoxypropanol, dipropylene glycol dimethyl ether, dipropylene glycol monomethyl ether or ethylene glycol dimethyl ether, and the like; glycol ether esters such as ethyl glycol acetate, butyl diglycol acetate, methoxypropyl acetate, and the like; glycols, such as propylene glycol and oligomers thereof, and the like; esters, specifically, for example, butyl acetate, isobutyl acetate, amyl acetate, and the like; ketones, specifically, for example, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone or the like; alcohols, specifically, methanol, ethanol, (iso) propanol, butanol, hexanol, or the like; n-alkylpyrrolidones, specifically, for example, N-ethylpyrrolidone and the like; aromatic hydrocarbons such as toluene or aliphatic hydrocarbons; paint solvent (S100), etc.; or a combination of any of the foregoing solvents.

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

The aforementioned catalyst may be, but is not limited to, an acid catalyst, a base catalyst, or a salt catalyst. The aforementioned defoaming agent may be, but is not limited to, polyether-based defoaming agent, silicone defoaming agent, mineral oil defoaming agent, or the like. The aforementioned photo-stabilizer may be, but is not limited to, a UV protective powder, a UV absorber (UVA), an inhibitor (quencher), or a Hindered Amine Light Stabilizer (HALS). The foregoing dispersant may be, but is not limited to, an anionic wetting dispersant, a cationic wetting dispersant, a non-ionic wetting dispersant, a zwitterionic wetting dispersant, an electrically neutral wetting dispersant, a polymeric hyperdispersant, a controlled radical hyperdispersant, or the like. The rheology modifier may be, but is not limited to, an inorganic rheology aid or an organic rheology aid, such as, specifically, a vinylpyrrolidone copolymer, a magnesium aluminum silicate crystalline hydrate, a non-associative thickener, an associative thickener, or a nonionic associative thickener, and the like. The aforementioned filler may be, but is not limited to, silica.

Examples

The present invention will be further illustrated in detail by examples hereinafter. However, it should be understood that these examples are only for the purpose of facilitating understanding of the present invention and are not intended to limit the scope of the present invention.

Sample preparation

Example 1

36g of melamine (Mel) and 99.9g of dimethyl carbonate (DMC) were put into 60g of n-butanol (NBA) to form a reaction mixture; 625g of a solution of 20% sodium tert-butoxide (STB) in n-butanol (NBA) was then added to the reaction mixture; the reaction mixture was warmed to 85 ℃ and stirred for 180 minutes under the aforementioned ambient conditions, after which the reaction mixture was cooled to room temperature; then 300g of a 25% aqueous solution of sulfuric acid was added to the reaction mixture and stirred until the reaction mixture was in a homogeneous phase; after the reaction mixture is kept still, draining the lower layer water of the reaction mixture; then stirring and washing the residual reaction mixture by water; then the reaction mixture is stood still and the water at the lower layer is discharged; then decompressing and heating to distill the reaction mixture to remove redundant water and NBA; adding NBA to dilute the reaction mixture; subsequently, the solid residue in the reaction mixture was filtered through a filter paper to obtain a TACT composition sample of example 1, and then DBC content was measured.

Example 2

36g of Mel and 88.8g of DMC were charged in 60g of NBA to form a reaction mixture; 625g of NBA solution containing 20% STB was then added to the reaction mixture; the reaction mixture was warmed to 85 ℃ and stirred for 180 minutes under the aforementioned ambient conditions, after which the reaction mixture was cooled to room temperature; then 300g of a 25% aqueous solution of sulfuric acid was added to the reaction mixture and stirred until the reaction mixture was in a homogeneous phase; after the reaction mixture is kept still, draining the lower layer water of the reaction mixture; then stirring and washing the residual reaction mixture by water; then the reaction mixture is stood still and the water at the lower layer is discharged; then decompressing and heating to distill the reaction mixture to remove redundant water and NBA; adding NBA to dilute the reaction mixture; subsequently, the solid residue in the reaction mixture was filtered through a filter paper to obtain a TACT composition sample of example 2, and then DBC content was measured.

Example 3

A180 g sample of the TACT composition of example 2 was taken and 2.62g of dibutyl carbonate (DBC) was added and stirred to obtain a sample of the TACT composition of example 3, and then the DBC content was measured.

Example 4

A sample of the TACT composition of example 2 (180 g) was sampled and mixed with DBC (10.57 g) to obtain a sample of the TACT composition of example 4, and then the DBC content was measured.

Example 5

A sample of TACT composition of example 1 (180 g) was sampled and mixed with DBC (12.45 g) to obtain a sample of TACT composition of example 5, and then the DBC content was measured.

Comparative example 1

36g of Mel and 95g of DMC were charged in 60g of NBA to form a reaction mixture; subsequently 586g of NBA solution containing 14.7% Sodium Methoxide (SM) were added to the reaction mixture; the reaction mixture was warmed to 85 ℃ and stirred for 180 minutes under the aforementioned ambient conditions, after which the reaction mixture was cooled to room temperature; then 345g of a 25% aqueous solution of sulfuric acid was added to the reaction mixture, and stirred until the reaction mixture became a uniform phase; after the reaction mixture is kept still, draining the lower layer water of the reaction mixture; then stirring and washing the residual reaction mixture by water; then the reaction mixture is stood still and the water at the lower layer is discharged; then decompressing and heating to distill the reaction mixture to remove redundant water and NBA; adding NBA to dilute the reaction mixture; subsequently, the solid residue in the reaction mixture was filtered through a filter paper to obtain a TACT composition sample of comparative example 1, and then DBC content measurement was performed.

Comparative example 2

Charging 36g of Mel and 111g of DMC into 60g of NBA to form a reaction mixture; 625g of NBA solution containing 20% STB was then added to the reaction mixture; the reaction mixture was warmed to 85 ℃ and stirred for 180 minutes under the aforementioned ambient conditions, after which the reaction mixture was cooled to room temperature; then 300g of a 25% aqueous solution of sulfuric acid was added to the reaction mixture and stirred until the reaction mixture was in a homogeneous phase; after the reaction mixture is kept still, draining the lower layer water of the reaction mixture; then stirring and washing the residual reaction mixture by water; then the reaction mixture is stood still and the water at the lower layer is discharged; then decompressing and heating to distill the reaction mixture to remove redundant water and NBA; adding NBA to dilute the reaction mixture; subsequently, the solid residue in the reaction mixture was filtered through a filter paper to obtain a TACT composition sample of comparative example 2, which was then subjected to DBC content measurement.

Comparative example 3

29g of Mel and 82.9g of DMC were charged in 972g of NBA to form a reaction mixture; 87g of 14.7% SM solid powder was then added to the reaction mixture; after warming the reaction mixture to 78 ℃ and stirring for 180 minutes under the aforementioned environment, the reaction mixture was cooled to room temperature; 338.2g of 30% aqueous nitric acid were then added to the reaction mixture and stirred until the reaction mixture was homogeneous; after the reaction mixture is kept still, draining the lower layer water of the reaction mixture; then stirring and washing the residual reaction mixture by water; then the reaction mixture is stood still and the water at the lower layer is discharged; then decompressing and heating to distill the reaction mixture to remove redundant water and NBA; adding NBA to dilute the reaction mixture; subsequently, the solid residue in the reaction mixture was filtered through a filter paper to obtain a TACT composition sample of comparative example 3, which was then subjected to DBC content measurement.

Detection of by-product DBC

In the detection of the DBC content as a by-product in each sample, detection was carried out by Gas chromatography (Gas chromatography) using an autosampler AOC-20i/AOC-20s (manufactured by SHIMADZU Corporation) and a Flame Ionization Detector (FID), under the following detection conditions:

carrier gas: nitrogen gas

Gas flow rate: 3.0 ml/min

Volume of gas: 1 ml of

Injection port temperature: 150 ℃ C

Detector temperature: 200 deg.C

Column: ZB-1(1.50mm, 0.53mm x 30m)

Detector temperature gradient curve: after the sample was injected, the oven temperature was held at 40 ℃ for 4 minutes, then the oven temperature was ramped up to 68 ℃ at a ramp rate of 3 ℃/minute, and then ramped up to 150 ℃ at a ramp rate of 7 ℃/minute for 5 minutes.

Total run time: 30.05 minutes

According to the GC spectrum analysis result, the by-product DBC of each sample is extracted when the retention time is 24-26 minutes, and the DBC content of each sample is further calculated through a calibration curve.

Calculation of the DBC content of the by-product

Drawing DBC calibration curve

Adding DBC standard substances of 500ppm, 1500ppm and 2500ppm into Tetrahydrofuran (THF) solution to prepare three different DBC standard solutions, measuring the area values of the DBC standard solutions under the GC measurement conditions, and drawing a DBC calibration curve shown in figure 1 according to the calculated area values and the corresponding DBC concentration values.

Method for calculating DBC content

Diluting a sample to be detected by 50 times with a THF solution, measuring the diluted sample under the GC measurement condition, calculating the area value of the DBC wave peak of the sample at the position of 24-26 minutes of the residence time, and then converting the DBC content of each sample through the drawn DBC calibration curve.

Film surface appearance test of coating

Preparing a coating composition from each sample according to the formula of the following table 1, diluting the coating composition to about 18-20 seconds of construction viscosity Ford No. 4 cup, respectively spraying and coating the diluted coating composition on a bottom plate, baking the coated bottom plates at 140 ℃ for 30 minutes after coating is finished to form a bottom plate with a coating layer with the thickness of 22-30 mu m, and observing the appearance of the surface of the coating film.

TABLE 1

Raw materials	Weight (wt%)
		Acrylic resin	63
Acid catalyst	1
		Butyl etherified amino resin	12.8
Samples of examples or comparative examples	9
		Paint solvent	10.65
N-butanol	3.55

Results of the experiment

Referring to table 2, table 2 shows the physical properties and process parameters of the TACT composition samples of examples 1 to 5 and comparative examples 1 to 3, and the results of the film surface appearance test of the coating compositions prepared from the samples; please refer to fig. 2, which is a photograph showing the test results of the coating materials of examples 1 to 5 and comparative examples 1 to 3.

TABLE 2

In table 2 above, the coating film surface appearance evaluation "normal" means that the coating film surface does not have any pin holes or sagging, and thus it can be seen from examples 1 to 5 of table 2 that controlling the DBC in the TACT composition to be 2 to 11 wt% of the total weight of the composition allows the coated object comprising the TACT composition to exhibit excellent coating film surface appearance after the coating composition is applied to the coated object; in contrast to comparative examples 1 to 3, the coating film surface coated with the coating composition containing the TACT composition of comparative example 1 exhibited pinholes, and the coating film surfaces of comparative examples 2 and 3 exhibited sagging, because DBC in the TACT composition was not controlled to account for 2 to 11 wt% of the total weight of the composition.

As described above, the tris (alkoxycarbonylamino) triazine (TACT) composition of the present invention, which includes TACT and dibutyl carbonate (DBC) in an amount of 2 to 11 wt% based on the total weight of the composition, can prevent a coated object from generating a pinhole or sagging after the coating composition including the same is coated, thereby exhibiting an excellent film surface appearance of a coating.

All ranges provided herein are intended to include each specific range within the given range as well as combinations of sub-ranges between the given ranges. Moreover, unless otherwise indicated, all ranges provided herein are inclusive of the endpoints of the ranges. Thus, ranges 1-5 specifically include 1,2,3, 4, and 5, as well as sub-ranges such as 2-5, 3-5, 2-3, 2-4, 1-4, and the like.

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 a discrepancy between this document and any publication or patent application incorporated by reference herein, this document controls.

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

Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients and/or reaction conditions are to be modified in all instances by the term "about" meaning within ± 5% of the number indicated. As used herein, the term "substantially free" or "substantially free" refers to less than about 2% of a particular feature. All elements or features positively set forth herein are negatively excluded from the claimed scope.

Claims

1. A tris (alkoxycarbonylamino) triazine (TACT) composition comprising TACT and dibutyl carbonate (DBC); wherein the DBC comprises 2 to 11 wt% of the total weight of the composition.

2. The composition of claim 1 wherein said DBC comprises from 3 to 8 wt% of the total weight of said composition.

3. The composition of claim 1, wherein the TACT has the structure of the following general formula (I):

wherein R is ₁ -R ₆ Each independently is H, NR ₇ R ₈ Or aliphatic; r is ₇ And R ₈ Independently H, aliphatic, alkoxy or carbamate.

4. The composition of claim 3, wherein R is ₂ 、R ₃ And R ₅ Is H.

5. The composition of claim 4, wherein R is ₁ 、R ₄ And R ₆ Is C1-C6 alkyl.

6. A composition as claimed in any one of claims 1 to 5, wherein the composition has a solids content of 45 to 60% by weight.

7. A composition according to any one of claims 1 to 5, wherein the pH of the composition at 25 ℃ is from 4.5 to 7.0.

8. The composition of any of claims 1 to 5, wherein the composition has a viscosity of 10 to 30cps at 25 ℃.

9. A process for the preparation of a composition as claimed in any one of claims 1 to 8, which comprises reacting a compound of the formula (II)

Reacting with carbonate in the presence of alcohol and alkali;

wherein R in the general formula (II) ₁ -R ₆ Each independently is H, NR ₇ R ₈ Or aliphatic; r ₇ And R ₈ Independently H, aliphatic, alkoxy or carbamate.

10. The preparation method of claim 9, further comprising additionally adding DBC to make it 2 to 11 wt% of the total weight of the composition.

11. The production process according to claim 9 or 10, wherein the carbonate is dimethyl carbonate.

12. The production method according to claim 9 or 10, wherein the base is an alkali metal alkoxide or an alkaline earth metal alkoxide.

13. The production method according to claim 12, wherein the alkali metal alkoxide is sodium tert-butoxide or sodium methoxide.

14. A coating composition comprising the TACT composition according to any of claims 1 to 8 as a crosslinker.