Open Time Additive

Abstract

The present disclosure is generally directed to open time additive compositions comprising at least two different open time additives having the structure of Compound I, a salt thereof, or both. Compound I has the following formula: (Compound I): JPEG2023541196000014.jpg8465.

Description

[Background technology]

[0001]

[0001] Paints are widely used across many industries and can generally be understood to include a pigment-containing carrier. However, this general view neglects that paints, particularly architectural paints, also provide a protective barrier or cover to a surface. Architectural paints benefit from improved workability (e.g., open time), where the paint is not yet dry and can be further spread (e.g., using a brush or roller). As such, coating compositions can vary widely depending on the application.

[0002]

[0002] Open time can be defined in several ways, but the term is generally used to indicate the time a coating allows smooth integration of subsequently applied paints and / or the time a coating remains workable and wet before curing. As previously discussed, open time can be an important aspect in characterizing paints because it can result in reduced buildup of coating defects, reduced labor costs, and / or reduced material costs to correct defects.

[0003]

[0003] Some known options for adjusting open time include increasing the water content, using glycol or glycerin esters, or using additives, which can significantly increase costs. Most of these solutions only provide a small / modest increase in open time and may have detrimental effects on other aspects of the paint's performance. In some regions, known options may also be listed as volatile organic compounds (VOCs), which are under strict global surveillance.

[0004]

[0004] Allowing sufficient time to apply, repair, or cover architectural coatings continues to be a challenge, especially in dry environments. Furthermore, paints with low pigment volume concentration (PVC), such as high solids content, and regions with strict VOC regulations can exacerbate the challenge. Summary of the Invention [Problem to be solved by the invention]

[0005]

[0005] There remains a need in the art for architectural coatings that contain an effective amount of open time additives to maintain workability under a variety of conditions. Furthermore, coatings that contain open time additives that can be modified to adjust workability due to variations in environmental conditions (e.g., humidity) could provide additional benefits to manufacturers and consumers. For example, customizing coating formulations by adjusting open time additives can lead to cost savings, especially in large construction projects. [Means for solving the problem]

[0006] In general, the present disclosure is directed to open time additive compositions, for example, for use with architectural paints. Architectural paints can be considered different from other paint, dye, or pigment-containing compositions in that architectural paints provide a coating for covering a surface and / or material. Thus, architectural paints can generally be used without modifying the surface and / or material to which they are applied. In contrast, dye or other pigment compositions can be used to incorporate the dye or a portion of the dye (e.g., pigment / colorant) into the material. Due, at least in part, to these differences, architectural paints can benefit from additives that can act to increase the open time of the architectural paint. In contrast, increasing the open time of a dye or other pigment composition can lead to undesirable bleeding. An exemplary implementation of the present disclosure is an open time additive composition comprising at least two different open time additives, i.e., a first open time additive and a second open time additive, wherein Compound I:

[0007] [ka]

[0008] wherein for both the first and second open time additives, m is an integer greater than or equal to 0, n is an integer greater than or equal to 0, and R1 and R2 are independently branched or linear carbon chains having greater than or equal to 1 and less than or equal to 40 carbon atoms; For both the first and second open time additives, each carbon atom of R1 and R2 is independently substituted with one or more hydrogen atoms, one or more hydroxyl groups, one or more other carbon atoms in a branched or linear carbon chain, an aryl group, or a combination thereof;

[0009] For both the first and second open time additives, each of R3 and R4 is independently a hydrogen atom or an ester group, such as an oleate group;

[0010] for the first open time additive, the sum of m and n is 5 or less;

[0011] For the second open time additive, the sum of m and n is 15 or greater.

[0009]

[0012] In a first example embodiment, m may be an integer greater than or equal to 5 and less than or equal to 100 for the second open time additive.

[0010]

[0013] In a second example embodiment, n may be 0 for the first open time additive.

[0011]

[0014] In a third example embodiment, n may be 5 or less and m is 5 or less for the first open time additive.

[0012]

[0015] In a fourth example embodiment, for one or both of the first and second open time additives, R3, R4, or both may be an ester group.

[0013]

[0016] In a fifth example embodiment, for one or both of the first and second open time additives, R1 and R2 may both be methyl groups.

[0014]

[0017] In a sixth example embodiment, the ester group is:

[0015] [ka]

[0016] It may also be an oleate group having the formula:

[0017]

[0018] In a seventh example embodiment, the weight ratio of the first open time additive to the second open time additive may be from 1:9 to 9:1.

[0018]

[0019] In an eighth example embodiment, the weight ratio of the first open time additive to the second open time additive may be from 1:3 to 3:1.

[0019]

[0020] In a ninth example embodiment, the weight ratio of the first open time additive to the second open time additive may be from 1:2 to 2:1.

[0020]

[0021] In a tenth example embodiment, the open time additive concentrate may be incorporated into an architectural coating composition comprising a solvent and a latex binder.

[0021]

[0022] In an eleventh example embodiment, the latex binder may include an acrylate.

[0022]

[0023] In a twelfth example embodiment, the solvent may be water.

[0023]

[0024] In a thirteenth example embodiment, the concentration of the open time additive in the architectural coating composition may be greater than or equal to about one-tenth percent and less than or equal to about five percent, based on the total weight of the architectural coating composition.

[0024]

[0025] In a fourteenth example embodiment, the architectural coating may have a solids content of about 10 percent or more and about 70 percent or less, based on the total weight of the architectural coating composition.

[0025]

[0026] In a fifteenth example embodiment, the open time additive and the latex binder may have a weight ratio of 1:999 to about 100:900, based on the total weight of the open time additive to the total weight of the latex binder.

[0026]

[0027] In a sixteenth example embodiment, the architectural coating may exhibit an increase in open time of 10 percent or more compared to the baseline open time exhibited by a baseline architectural coating, which may not include an open time additive and may have approximately the same relative composition with respect to other components included in the architectural coating, and the open time may be determined in accordance with the OTA test, ASTM D7488-11 "Standard Test Method for Open Time of Latex Paints."

[0027]

[0028] In a seventeenth example embodiment, the architectural coating may have a volatile organic compound (VOC) content of less than 1 part per thousand percent based on the total weight of the architectural coating, where the VOC content may be determined in accordance with EPA Method 24.

[0028]

[0029] Each of the example aspects listed above may be combined with one or more of the other example aspects listed above in certain embodiments. For example, all of the 18 example aspects listed above may be combined with each other in some embodiments. As another example, any combination of two, three, four, five, or more of the 18 example aspects listed above may be combined in other embodiments. Thus, the example aspects listed above may be utilized in combination with each other in some example embodiments. Alternatively, the example aspects listed above may be implemented individually in other example embodiments. Thus, it will be understood that various example embodiments may be realized utilizing the example aspects listed above.

[0029]

[0030] Other features and aspects of the disclosure are discussed in more detail below. DETAILED DESCRIPTION OF THE INVENTION

[0030]

[0031] Those skilled in the art will appreciate that this disclosure is merely a description of exemplary embodiments and is not intended as a limitation on the broader aspects of the present disclosure.

[0031]

[0032] The present disclosure is generally directed to open time additives having the structure of Compound I, a salt thereof, or both. Compound I has the following formula:

[0032] [ka]

[0033] It has. The open time additive composition may include at least two different open time additives, i.e., a first open time additive and a second open time additive, having the formula of Compound I. For both the first and second open time additives: m is an integer greater than or equal to 0, n is an integer greater than or equal to 0, R1 and R2 are independently a branched or linear carbon chain having 1 or more and 40 or less carbon atoms; each carbon atom in R1 and R2 is independently substituted with one or more hydrogen atoms, one or more hydroxyl groups, one or more other carbon atoms in the branched or linear carbon chain, an aryl group, or a combination thereof; and each of R3 and R4 is independently a hydrogen atom or an ester group, such as an oleate group. For the first open time additive, the sum of m and n is 5 or less. For the second open time additive, the sum of m and n is 15 or more.

[0034] The ester group has the following formula:

[0035] [ka]

[0036] In certain exemplary embodiments, the ester group may be a saturated or unsaturated C6 to C22 ester group, such as stearate (C18, saturated), oleate (C18, unsaturated), linoleate (C18, unsaturated), palmitate (C16, saturated), laurate (C12 saturated), decanoate (C10, saturated), or octanoate (C8, saturated).

[0037] Some embodiments of the present disclosure may include a weight ratio of the first open time additive to the second open time additive. For example, the weight ratio of the first open time additive to the second open time additive may be 1:9 to 9:1, such as 1:3 to 3:1, such as 1:2 to 2:1. Such a weight ratio can advantageously increase the open time when the open time additive composition is added to an architectural coating, for example, increasing the open time by 20% compared to an untreated control, without negatively impacting scuff resistance, and with adequate stain resistance compared to a single open time additive.

[0038] The open time additive composition may be incorporated into an architectural coating. In one exemplary implementation, the architectural coating includes a solvent, a latex binder (e.g., a polymer containing one or more acrylates, vinyl acetate, vinyl chloride, and / or styrene-butadiene monomers), and an open time additive. Optionally, the architectural coating may further include a dispersant and / or surfactant to improve distribution of the latex binder throughout the architectural coating. In this manner, the dispersant and / or surfactant may be used to produce a more homogeneous mixture, which may result in a smoother coating of the architectural coating. Optionally, the architectural coating may include a thickener to adjust the viscosity of the architectural coating to improve adhesion of the wet coating to an applicator (e.g., a brush or roller). Optionally, the architectural coating may include one or more pigments (e.g., TiO2) to impart color to the architectural coating. Optionally, the architectural coating may include a cosolvent (e.g., ethylene glycol) to improve the solubility of the architectural coating's components.

[0039]

[0036] Embodiments of example embodiments according to the present disclosure may contain low levels of volatile organic compounds (VOCs). High VOCs not only present a personal hazard to painters working in confined and / or unventilated spaces, but are also recognized as an environmental hazard. In these spaces, VOCs can accumulate in the air, which can cause respiratory problems and potential health concerns for painters. Many known paint additives used to modify the open time of paints are known for their high VOCs and have presented challenges. Poor open time performance can require increased work time to correct mistakes, such as streaking, that are inherent in paint compositions. Therefore, improving open time while simultaneously reducing VOC content can provide significant benefits in the cost and efficiency of painting projects and the health of painters.

[0040] Another aspect of the exemplary implementation may include certain latex binders. The latex binder may include various polymers suitable for architectural coatings, such as acrylates (e.g., polymethyl methacrylate), which may be formed as homopolymers or copolymers. For example, copolymers may include the incorporation of another monomer (e.g., butadiene styrene). In some implementations, the acrylate may be modified to include one or more nitrile groups. Thus, the latex binder may include various acrylates, acrylate butadiene styrene copolymers, and acrylonitrile butadiene styrene copolymers. Furthermore, these latex binders are presented for illustrative purposes, and additional latex binders may be used alone or in combination with the implementations of the present disclosure.

[0041] By way of example, an implementation of the present disclosure may include an architectural coating comprising a latex binder having an acrylate. The acrylate may include a polymer or copolymer comprising one or more acrylate monomers. An example embodiment of an acrylate polymer or copolymer may include a mass fraction of the acrylate monomer. For example, the acrylate may include a copolymer comprising an acrylate monomer (e.g., methyl methacrylate) and a second monomer (e.g., butadiene styrene). The mass fraction of the acrylate monomer relative to the total weight of the copolymer may define the mass fraction. In some acrylates, the mass fraction of the acrylate monomer relative to the total weight of the copolymer may be about 20 wt% or more and about 100 wt% or less, such as about 30 wt% or more and about 80 wt% or less, about 40 wt% or more and about 70 wt% or less, or about 45 wt% or more and about 60 wt% or less (e.g., 100 wt%, 95 wt%, 90 wt%, 85 wt%, 80 wt%, 75 wt%, 70 wt%, 65 wt%, 60 wt%, 55 wt%, or 50 wt%). In particular, certain implementations may include acrylates having a mass fraction of the acrylate monomer relative to the total weight of the acrylates that is greater than 50 wt%.

[0042]

[0039] For certain exemplary implementations of the present disclosure, the open time additive may include two or more of 1,3-bis(2-(hydroxypolyethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione, 1,3-bis(2-(hydroxypolyethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione monoester, and 1,3-bis(2-(hydroxypolyethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione diester. Each of these compounds can be obtained from the formula of Compound I, where n is 1 or more and 100 or less, m is 1 or more and 100 or less, and R1 and R2 are each a straight carbon chain containing one carbon atom (e.g., a methyl group) substituted with three hydrogen atoms; Compound I, where R1 and R2 are each a straight carbon chain containing one carbon atom (e.g., a methyl group) substituted with three hydrogen atoms, and R4 or R3 is an ester group; and Compound I, where R1 and R2 are each a straight carbon chain containing one carbon atom (e.g., a methyl group) substituted with three hydrogen atoms, and R4 and R3 are both ester groups.

[0043] In embodiments where the open time additive includes an oleate group, it should be understood that the oleate group is attached such that the carbonyl carbon is linked to the terminal oxygen (at R3 and / or R4) to form an ester. Thus, the oleate group is depicted to show a fatty acid carbon chain (17 carbons, monounsaturated) attached to the carbonyl carbon, and a second bond to indicate the point of attachment of Compound I to the oleate group.

[0044] Furthermore, in the practice of the present disclosure, it should be understood that in open time additives based on Compound I, the degrees of polymerization n and m may be different (e.g., n and m may have different values, such as n=4 and m=5) or may be the same (e.g., n=4 and m=4). Furthermore, certain implementations may include combinations of open time additives based on Compound I, such as architectural coatings containing both 1,3-bis(2-(hydroxypolyethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione and 1,3-bis(2-(hydroxypolyethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione monooleate.

[0045] Exemplary embodiments formulated in accordance with the present disclosure may provide additional benefits in formulating low-VOC architectural coatings. In particular, exemplary embodiments may include solvents that may be considered low-VOC or VOC-free. For example, water is not an organic compound and, therefore, is preferably incorporated into architectural coatings of the present disclosure. In addition to water, cosolvents may be included to improve the solubility of architectural coating components (e.g., open-time additives, surfactants, pigments, etc.). Exemplary cosolvents may be VOC-exempt (e.g., acetone, dimethyl carbonate, methyl acetate, parachlorobenzotrifluoride, tert-butyl acetate, and propylene carbonate) or may be added at low concentrations (e.g., low weight percent) to limit the VOC concentration of the architectural coating.

[0046] For example, certain implementations of the present disclosure may include architectural coatings having a VOC content of less than one thousandth of a percent (<0.001%) based on the total weight of the architectural coating. VOC content may be determined using various methods, and preferably, exemplary implementations may include a specified VOC content determined in accordance with EPA Method 24 for Surface Coatings.

[0047] Alternative methods for determining VOC content may be used to determine VOC content in some exemplary implementations. For example, ASTM D6886-14 does not specifically identify what constitutes a VOC component based on chemical properties, but rather implies that any component that produces a peak in a gas chromatogram is considered a VOC (exempt or non-exempt). Furthermore, IOS 11890-2 may be used to determine VOC content based on a predefined boiling point limit. As an example, when the term "VOC" is used for a compound whose boiling point is below the boiling point limit, a marker compound is used that has a known purity and a boiling point (BP) within ±3°C of the defined maximum. Thus, if the EU definition of VOC is adopted (i.e., any compound with a boiling point below 250°C is classified as a VOC), tetradecane (with a BP of 252.6°C) or a nonpolar compound with a similar boiling point may be used as a marker compound for nonpolar systems, while diethyl adipate (with a BP of 251°C) may be used for polar systems.

[0048] Exemplary implementations according to the present disclosure may include a VOC content of greater than or equal to one part in one hundred thousandth of a percent (0.00001%) and less than or equal to one part in one thousandth of a percent (0.001%), such as greater than or equal to five parts in one hundred thousandths of a percent (0.00005%) and less than or equal to eight parts in one thousandths of a percent (0.0008%), or greater than or equal to one part in one thousandth of a percent (0.0001%) and less than or equal to five parts in one thousandths of a percent (0.0005%), as determined using one of the methods disclosed herein (e.g., EPA Method 24). In some implementations, the VOC content may be substantially zero, including, for example, a substantially undetectable amount of VOCs based on the analytical means (e.g., gas chromatograph) used to determine the VOC content.

[0049] In exemplary implementations, the open time additive can be added to an architectural coating in an effective amount to reduce streaking, even in environments with low humidity. For example, the open time additive can be included in a concentration of about one-tenth percent (0.1%) or more and about five percent (5%) or less, such as about one-half percent (0.5%) or more and about four and a half percent (4.5%) or less, about one percent (1.0%) or more and about four percent (4.0%) or less, about one and a half percent (1.2%) or more and about three and a half percent (3.5%) or less, and about two percent (2%) or more and about three percent (3%) or less, based on the weight of the open time additive relative to the total weight of the architectural coating.

[0050]

[0047] Example embodiments of open time additives may include the substructure of Compound I. Some example substructures can include compounds where m is 5 or greater and 100 or less. Another example substructure can include compounds where n is 0. Further example substructures can include compounds where n is 10 or less and m is 10 or less. Additionally or alternatively, further example substructures can include compounds where R3 and / or R4 are oleate groups.

[0051]

[0048] Another aspect of some implementations according to the present disclosure may include a solids content of greater than or equal to five percent (5%) and less than or equal to seventy percent (70%), such as greater than or equal to eight percent (8%) and less than or equal to fifty percent (50%), or greater than or equal to ten percent (10%) and less than or equal to thirty percent (30%) [e.g., twelve percent (12%), fourteen percent (14%), fifteen percent (15%), sixteen percent (16%), or eighteen percent (18%)], based on the total weight of the open time additive relative to the total weight of the latex binder.

[0052] Some embodiments of the present disclosure may include a weight ratio of open time additive to latex binder. Advantageously, the weight ratio of open time additive to latex binder is 1:999 or less and 1:9 or more, such as 1:900 or less and 1:9 or more, 1:800 or less and 1:9 or more, 1:800 or less and 1:90 or more, or 1:800 or less and 1:200 or more (e.g., 1:900, 1:800, 1:700, 1:600, 1:500, 1:400, 1:300, 1:200, or 1:100).

[0053] As used herein, the weight ratio of open time additive to latex binder should be understood based on the open time additive. Thus, 1:999 or less should be read as meaning that for each weight unit of open time additive, there are 999 or less weight units of latex binder. As another example, 1:9 or more should be read as meaning that for each weight unit of open time additive, there are 9 or more weight units of latex binder.

[0054] In the practice of the present disclosure, architectural coatings may contain a certain amount of pigment or may be formulated to contain a certain amount of pigment. For example, a particular example architectural coating may contain a pigment, where the pigment comprises titanium dioxide (TiO2) at a concentration of 15 wt% or more TiO2 and 60 wt% or less TiO2, based on the total weight of the architectural coating. TiO2 may be used to impart whiteness and / or opacity to example implementations and may be included to enhance viscosity. Generally, example implementations may contain 15 wt% or more and 60 wt% or less TiO2, such as 18 wt% or more and 55 wt% or less TiO2, 20 wt% or more and 50 wt% or less TiO2, or 25 wt% or more and 45 wt% or less TiO2.

[0055] One example aspect of certain implementations can include an increase in open time resulting from the addition of an open time additive to a coating composition. A base coating having a composition without an open time additive can be modified to produce an architectural coating by adding an effective amount of an open time additive to the base coating to determine the increase in open time. For some implementations, the addition of an effective amount of an open time additive to the base coating can result in an increase in the open time determined for the architectural coating of ten percent (10%) or more, such as twenty percent (20%) or more, compared to the base coating alone. Open time can be determined using various methods, and preferably, implementations according to the present disclosure can determine open time in accordance with OTA test ASTM D7488-11, "Standard Test Method for Open Time of Latex Paints."

[0056] Alternatively or additionally, another example aspect of certain implementations can include increased abrasion resistance resulting from the addition of an open time additive to a coating composition. To determine increased abrasion resistance, a test method such as ASTM D 2486 can be used to compare the number of abrasions to the failure and / or exposure of the substrate material after a number of abrasions. For example, a first coating can be applied to the substrate material using a base paint, and a second coating can be applied to the substrate material using an architectural paint, the architectural paint being formulated by adding an effective amount of an open time additive to the base paint. After applying an abrasive force (e.g., rubbing) to the coating, abrasion resistance can be determined based at least in part on the removal of the coating and / or the exposure of the substrate material. In some implementations, the addition of an effective amount of open time additive may result in an increase in abrasion resistance (compared to the base paint) of greater than or equal to one-quarter percent (0.25%) and less than or equal to sixty percent (60%), such as greater than or equal to ten percent (10%) and less than or equal to fifty percent (50%), greater than or equal to twelve percent (12%) and less than or equal to forty (40%), or greater than or equal to fifteen (15%) and less than or equal to thirty (30%).

[0057]

[0054] Practice of the present disclosure may also include a method for adjusting the open time of a base paint (e.g., a water-based latex paint). The method may include forming a water-based latex paint (e.g., a water-based acrylate) containing an open time additive having the structure of Compound I or the basic structure of Compound I described herein.

[0058] One example embodiment of forming a water-based latex paint containing an open time additive may include homogenizing the water-based latex paint while adding the open time additive. Homogenizing may include various forms of mixing to promote the incorporation of the open time additive by the water-based latex paint. For example, homogenizing may include mixing the water-based latex paint at a specified revolutions per minute (RPM), sonicating the water-based latex paint at a specified frequency, and / or vortexing the water-based latex paint. In this manner, the open time additive is incorporated throughout the water-based latex paint, producing an architectural paint according to an example implementation of the present disclosure. Thus, example implementations may further include a method of producing an architectural paint, such as an example architectural paint of the present disclosure, using an example method of the present disclosure.

[0059] Another embodiment of the method for producing an architectural coating may include determining the solids content of a base coating (e.g., a water-based latex coating) and adding an amount of Compound I to the base coating based at least in part on the solids content. In particular, the solids content can determine the basis for adding an effective amount of open time additive. For example, the amount of latex binder can be determined based on the solids content, and the effective amount of open time additive can be determined according to the ratio of open time additive to latex binder disclosed in the exemplary embodiments herein.

[0060]

[0057] Certain methods of producing architectural coatings according to the present disclosure may further include a step of modifying compound I by adjusting the degree of polymerization (e.g., by selecting m and / or n) to modify the open time of the water-based latex coating.

[0061] The foregoing description is exemplary in nature and is in no way intended to limit the scope, applicability, or configuration of the present disclosure. Various changes to the described embodiments may be made in the function and arrangement of elements described herein without departing from the scope of the present disclosure.

[0062] As used in this specification and claims, the singular forms "a," "an," and "the" include the plural forms unless the context clearly dictates otherwise. Furthermore, the term "includes" means "comprises." The methods and compositions of the present disclosure may include, consist of, or consist essentially of the essential elements and limitations of the embodiments described herein, including their components, as well as any additional or optional ingredients, components, or limitations useful in nutritional compositions described herein or otherwise.

[0063]

[0060] Unless otherwise specified, any numbers expressing quantities or properties of ingredients, e.g., molecular weight, percentages, etc., used in the specification or claims should be understood to be modified by the term "about." Thus, unless otherwise specified, implicitly or explicitly, the numerical parameters given are estimates that may depend on the desired properties sought and / or detection limits under standard test conditions / methods. When directly and clearly distinguishing the embodiments from the stated prior art, the numbers of the embodiments are not approximations unless the word "about" is recited.

[0064]

[0061] As used herein, "optional" or "optionally" means that the subsequently described material, event, or circumstance may or may not be present or occur, and that the description includes instances where the material, event, or circumstance is present or occurs and instances where it is not present or occurs. As used herein, "wt%" and "w / w%" mean weight as a percentage of the total weight or weight relative to another component in a composition.

[0065]

[0062] The term "about" is intended to mean approximately, in the region of, roughly, or around. When the term "about" is used in conjunction with a numerical range, it modifies that range by extending the boundaries above and below the set forth numerical values. Unless otherwise specified, it should be understood that the numerical parameters set forth in the following specification and appended claims are estimates. Finally, without intending to limit the application of the doctrine of equivalents to the claims, the numerical parameters should be read in light of the number of reported significant digits and the application of ordinary rounding techniques.

[0066]

[0063] The phrase "effective amount" refers to an amount of a compound that promotes, improves, stimulates, or otherwise affects a response to a particular disease or disorder, or a particular symptom of a disease or disorder.

[0067]

[0064] The present disclosure may be better understood with reference to the following examples. [Example]

[0068] Various formulations were prepared in accordance with the present disclosure and tested for wet edge to open time ratio (WE / OT); open time (OT), and dry to touch (DTT). A standard paint having a solids of 40% pigment volume concentration (PVC) was used for comparison. Two percent (2%) amounts of open time additives according to the present disclosure (DS 7034, DS 7036, and combinations thereof) were incorporated into blank paints. Each of these formulations was characterized using the OTA test ASTM D7488-11, "Standard Test Method for Open Time of Latex Paints," and the collected results are shown in Table 1. DS 7034 was an open time additive according to the present disclosure with a long-chain ester, i.e., an oleate group; DS 7036 was an open time additive according to the present disclosure with a medium-chain ester, i.e., an ester shorter than the oleate group of DS 7034.

[0069]

[0066]

[0070] [Table 1]

[0071]

[0067]

[0072] [Table 2]

[0073] During testing, a wet edge line may be visually observed near the edge of the paint surface, with a value determined at least in part based on the time at which the edge of the paint can no longer be incorporated into the body of the paint minus the time to reapplication. Additionally, open time may be visually observed by streaking, with a value determined based on the time at which an "X" is visible after a paint cycle minus the time to repair. As shown in Tables 1 and 2, all open time additives according to example embodiments of the present disclosure extended open time compared to the standard paint by at least one of the criteria evaluated.

[0074]

[0069]

[0075] [Table 3]

[0076]

[0070] Exemplary methods ISO 11890-2, ASTM D6886-14, and EPA Method 24 were performed to determine VOC content, as shown in Table 3, and the results of each method were compared for the example open time additives (OTAs) DS 7034 and DS 7036. The results are summarized in Table 4, which also includes thermal properties such as melting point and boiling point. The boiling point was determined based on the onset temperature of the large endotherm observed using dynamic scanning calorimetry (DSC) analysis and the significant weight loss that occurred in a thermogravimetric analysis (TGA) scan. In EPA Method 24, the VOC criteria were based on weight loss (corrected for water content) after 1 hour in a 110°C oven.

[0077]

[0071]

[0078] [Table 4]

[0079] The open time additives of the examples were also tested to determine their effect on abrasion resistance. Standard method ASTM D 2486 was used to determine abrasion resistance, and the increase in abrasion resistance relative to a blank paint (i.e., a paint without open time additives) was determined. Unexpectedly, it was found that the open time additives did not increase or decrease abrasion resistance (e.g., peeling of an architectural paint from a surface). To understand the effect of the open time additives, commercial paints were tested. Freshly formulated paints were used to compare a blank sample containing only the commercial paint and test samples containing 2% of various open time additives. The results of the examples are shown in Table 5, which demonstrate the increase in abrasion resistance relative to the blank paint.

[0080]

[0073]

[0081] [Table 5]

[0082] During testing, a coating of either the blank paint or the paint containing 2% open time additive was applied to a dark substrate, and after each coating was subjected to a similar sanding process, the paint loss based on the appearance of the substrate was determined.

[0083] The open time additives of the examples were also tested to determine the effect of the open time additive on stain resistance. Standard method ASTM D 4828 was used to determine stain resistance and the increase in stain resistance was determined. To understand the effect of the open time additives, commercial paints containing various open time additives were tested. The results of the examples are shown in Table 6 and demonstrate the change in stain resistance.

[0084]

[0076]

[0085] [Table 6]

[0086]

[0077] For the test, a coating of paint containing 2% open time additive was applied to a substrate, and a streaking of each stain or dirt was applied to the coating. After mechanically rubbing each coating, the condition of each stain / dirt was determined based on the appearance of the substrate. The following ratings were used: "0" corresponds to no change in the original intensity of the stain or dirt; "3" corresponds to a slight change in the original intensity of the stain or dirt, so that the stain or dirt is easily visible; "5" corresponds to a moderate change in the original intensity of the stain or dirt, so that the stain or dirt is only slightly visible; "7" corresponds to a large change in the original intensity of the stain or dirt, so that the stain or dirt is barely visible; and "10" corresponds to complete removal of the stain or dirt. The comparison in parentheses indicates the relative difference in stain resistance between the coating containing 2% open time additive and the blank coating without open time additive for each evaluation, with "=" corresponding to the same stain resistance, "-" corresponding to lower stain resistance, "sl-" corresponding to slightly lower stain resistance, "sl+" corresponding to slightly better stain resistance, and "+" corresponding to better stain resistance. As can be seen in Table 6, DS 7034 had a negative effect on the stain test with pen, purple crayon, grape juice, and coffee, DS 7036 had a slightly negative effect on coffee only, and DS 7034 / DS7036 (1:2) was able to prevent the stain effect of DS 7034.

[0087]

[0078] These and other modifications and variations of the present disclosure may be practiced by those skilled in the art without departing from the spirit and scope of the present invention, which is more particularly set forth in the appended claims. Furthermore, it should be understood that aspects of the various embodiments may be interchanged both in whole or in part. Furthermore, those skilled in the art will appreciate that the foregoing description is by way of example only and is not intended to limit the invention, which is further set forth in such appended claims.

Claims

1. a first open time additive having the structure of Compound I, a salt thereof, or both; a second open time additive having the structure of Compound I, a salt thereof, or both; An open time additive composition comprising: Compound I is: 【Chemical 1】 wherein for both the first and second open time additives, m is an integer greater than or equal to 0, n is an integer greater than or equal to 0, and R1 and R2 are independently branched or linear carbon chains having greater than or equal to 1 and less than or equal to 40 carbon atoms; for both the first and second open time additives, each carbon atom of R1 and R2 is independently substituted with one or more hydrogen atoms, one or more hydroxyl groups, one or more other carbon atoms in the branched or linear carbon chain, an aryl group, or a combination thereof; For both the first and second open time additives, each of R3 and R4 is independently a hydrogen atom or an ester group; for the first open time additive, the sum of m and n is 5 or less; for the second open time additive, the sum of m and n is 15 or greater; Open time additive composition.

2. 10. The open time additive composition of claim 1, wherein m is an integer greater than or equal to 5 and less than or equal to 100 for the second open time additive.

3. 3. The open time additive composition of claim 1 or 2, wherein for the first open time additive, n is 0.

4. For the first open time additive: n is 5 or less, m is 5 or less; The open time additive composition of any one of claims 1 to 3.

5. 5. The open time additive composition of claim 1, wherein for one or both of the first and second open time additives, R3, R4, or both are the ester group.

6. 6. The open time additive composition of claim 1, wherein for one or both of the first and second open time additives, R1 and R2 are both methyl groups.

7. The ester group has the formula: 【Chemistry 2】 7. The open time additive composition of claim 1, wherein the oleate group has the formula:

8. 8. The open time additive composition of any one of claims 1 to 7, wherein the weight ratio of the first open time additive to the second open time additive is from 1:9 to 9:

1.

9. 9. The open time additive composition of any one of claims 1 to 8, wherein the weight ratio of the first open time additive to the second open time additive is from 1:3 to 3:

1.

10. 10. The open time additive composition of any one of claims 1 to 9, wherein the weight ratio of the first open time additive to the second open time additive is from 1:2 to 2:

1.

11. a solvent; a latex binder; The open time additive composition according to any one of claims 1 to 10.

1. An architectural coating composition comprising:

12. 12. The architectural coating composition of claim 11, wherein the latex binder comprises an acrylate.

13. 13. The architectural coating composition of claim 11 or 12, wherein the solvent is water.

14. 14. The architectural coating composition of any one of claims 11 to 13, wherein the concentration of the open time additive in the architectural coating composition is greater than or equal to about one-tenth of a percent and less than or equal to about five percent, based on the total weight of the architectural coating composition.

15. 15. The architectural coating composition of any one of claims 11 to 14, having a solids content of about 10 percent or more and about 70 percent or less, based on the total weight of the architectural coating composition.

16. 16. The architectural coating composition of any one of claims 11 to 15, wherein the open time additive and the latex binder have a weight ratio of 1:999 to about 100:900, based on the total weight of the open time additive to the total weight of the latex binder.

17. exhibiting an increase in open time of 10 percent or more compared to the baseline open time exhibited by a baseline architectural coating; The baseline architectural coating does not contain the open time additive and has a relative composition that is approximately the same with respect to other components contained in the architectural coating composition, and the open time is determined in accordance with the OTA test, ASTM D7488-11 "Standard Test Method for Open Time of Latex Paints"; 17. The architectural coating composition of any one of claims 11 to 16.

18. 18. The architectural coating composition of any one of claims 11 to 17, having a volatile organic compound (VOC) content of less than 1 part in 1000 percent, based on the total weight of the architectural coating composition, wherein the VOC content is determined in accordance with EPA Method 24.

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