Acrylic resin having ureido functional group

Abstract

The present application relates to an acrylic resin suitable for two-component polyurethane coating applications. Provided herein is an acrylic resin comprising: at least one epoxy silane oligomer wherein the epoxy silane oligomer is grafted to at least one hydroxyl group of the acrylic resin; wherein at least one hydroxyl group of the acrylic resin has at least one ureido functional group; and wherein at least one hydroxyl group of the acrylic resin has at least one acid group. Also disclosed is a two-component coating system comprising an acrylic resin comprising at least one hydroxyl group and at least one epoxy silane oligomer wherein the at least one hydroxyl group of the acrylic resin has at least one ureido functional group.

Description

Technical Field

[0001] The present disclosure generally relates to compositions for resins, and more specifically to acrylic resins comprising at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted onto at least one hydroxyl group of the acrylic resin; wherein the at least one hydroxyl group of the acrylic resin has at least one urea functional group; and wherein the at least one hydroxyl group of the acrylic resin has at least one acid group. Also disclosed is a two-component coating system comprising an acrylic resin comprising at least one hydroxyl group and at least one epoxy silane oligomer, wherein at least one hydroxyl group of the at least one acrylic resin has at least one urea functional group. Background Art

[0002] Conventional polyurethane primers typically offer fast-curing properties. However, in direct-to-metal (DTM) applications without an etch primer layer, polyurethane primers typically lack sufficient adhesion. Etching the primer layer is an extra step in the coating process and is generally undesirable. To improve adhesion in DTM applications, epoxy primers can be used instead of polyurethane primers, but they cure slowly. Although some properties may improve with changes in the polyurethane and coating formulations, other properties may be affected by these modifications.

[0003] Manufacturers, especially those of wood, plastics, electronics, automobiles, aerospace, marine, general industry and other consumer goods, are increasingly demanding these specific properties of primers. Manufacturers are constantly searching for coatings that exhibit these improved properties (such as adhesion and fast drying time) without sacrificing other properties. In view of these challenges to many conventional polyurethane primers, there remains a need for improved coatings with binding agents that can provide adhesion and other improved properties and other advantages. Additionally, there is a need for improved coatings that provide properties substantially the same as those of epoxy primers. Summary of the Invention

[0004] The embodiments described herein are not intended to be exhaustive or limiting of the content disclosed in the claimed subject matter and in the detailed description. Instead, the embodiments are selected and described so that others skilled in the art can recognize and understand the principles and practices provided in the claimed subject matter.

[0005] An acrylic resin and method for preparing the same are shown and described. The acrylic resin may comprise at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted onto at least one hydroxyl group of the acrylic resin; wherein the at least one hydroxyl group of the acrylic resin has at least one urea-functional group; and wherein the at least one hydroxyl group of the acrylic resin has at least one acid group. In some embodiments, the acrylic resin has a Tg of between 10°C and 90°C as measured by differential scanning calorimetry (DSC) using ASTM D6604-00. In another embodiment, the urea-functional group comprises a urea-based monomer having a (meth)acrylate group and a cyclic urea group.

[0006] Additionally, a two-component coating system is provided, comprising: 1) a first part comprising at least one isocyanate; and 2) a second part comprising the acrylic resin described herein.

[0007] To achieve the aforementioned and related purposes, the following description illustrates certain exemplary aspects and embodiments. These representations may employ some of the various methods of one or more aspects. When considered, other aspects, advantages, and novel features of the present disclosure will become apparent from the following detailed description. DETAILED DESCRIPTION

[0008] Aspects of the present disclosure are disclosed in the following descriptions related to specific embodiments. Alternative embodiments may be devised without departing from the scope of the present disclosure. In addition, well-known embodiments of the present disclosure may not be described in detail or may be omitted so as not to obscure the relevant details of the present disclosure. Further, to facilitate understanding of this specification, several terms used herein are discussed below.

[0009] As used herein, the word "exemplary" means "serving as an example, instance, or illustration." The embodiments described herein are not limiting, but merely exemplary. It should be understood that the described embodiments are not necessarily to be construed as preferred or advantageous over other embodiments. Furthermore, the term "embodiment" does not require that all embodiments include the discussed feature, advantage, or mode of operation.

[0010] The present disclosure generally relates to adhesives that offer advantageous improvements over current resins. It has been discovered that the use of specific acrylic resins comprising at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted onto at least one hydroxyl group of the acrylic resin; wherein at least one hydroxyl group of the acrylic resin has at least one urea functional group; and wherein at least one hydroxyl group of the acrylic resin has at least one acid group, can provide improved adhesion and fast drying properties over conventional polyurethane and epoxy resins. In some embodiments, the acrylic resins described herein can be used in coatings. In one embodiment, the coating can be a primer. In another embodiment, the coating can be a topcoat.

[0011] The number of milligrams of potassium hydroxide required to neutralize 1 gram of solution is called the hydroxyl number (which may also be referred to as the hydroxyl value), as discussed in ASTM D4274-11.2. This wet chemical method is complex, time-consuming, and requires multiple reagents. More recently, Fourier transform near-infrared (FT-NIR) spectroscopy has been used to determine the hydroxyl value of various materials according to ASTM D6342-12. In many embodiments, the acrylic resin has a hydroxyl number of 50 mg KOH / g to 250 mg KOH / g. In other embodiments, the acrylic resins described herein may have a hydroxyl number, for example, in the following ranges: 50 mg KOH / g to 240 mg KOH / g, 50 mg KOH / g to 230 mg KOH / g, 50 mg KOH / g to 220 mg KOH / g, 50 mg KOH / g to 210 mg KOH / g, 50 mg KOH / g to 200 mg KOH / g, 50 mg KOH / g to 190 mg KOH / g, 50 mg KOH / g to 180 mg KOH / g, 50 mg KOH / g to 170 mg KOH / g, 50 mg KOH / g to 150 mg KOH / g, 50 mg KOH / g to 140 mg KOH / g, 50 mg KOH / g to 130 mg KOH / g, 50 mg KOH / g to 110 mg KOH / g, 50 mg KOH / g to 100 mg KOH / g, 60 mg KOH / g to 800 mg KOH / g, KOH / g to 250 mg KOH / g, 60 mg KOH / g to 240 mg KOH / g, 60 mg KOH / g to 230 mg KOH / g, 60 mg KOH / g to 220 mg KOH / g, 60 mg KOH / g to 210 mg KOH / g, 60 mg KOH / g to 200 mg KOH / g, 60 mg KOH / g to 190 mg KOH / g, 60 mg KOH / g to 180 mg KOH / g, 60 mg KOH / g to 170 mg KOH / g, 60 mg KOH / g to 150 mg KOH / g, 60 mg KOH / g to 140 mg KOH / g, 60 mg KOH / g to 130 mg KOH / g, 60 mg KOH / g to 110 mg KOH / g, 60 mg KOH / g to 100 mg KOH / g, 70 mg KOH / g to 250mg KOH / g, 70mg KOH / g to 240mg KOH / g, 70mg KOH / g to 230mg KOH / g, 70mg KOH / g to 220mg KOH / g, 70mg KOH / g to 210mg KOH / g, 70mg KOH / g to 200mg KOH / g, 70mg KOH / g to 190mg KOH / g, 70mgKOH / g to 180 mg KOH / g, 70 mg KOH / g to 170 mg KOH / g, 70 mg KOH / g to 150 mg KOH / g, 70 mg KOH / g to 140 mg KOH / g, 70 mg KOH / g to 130 mg KOH / g, 70 mg KOH / g to 110 mg KOH / g, 70 mg KOH / g to 100 mg KOH / g, 80 mg KOH / g to 250 mg KOH / g, 80 mg KOH / g to 240 mg KOH / g, 80 mg KOH / g to 230 mg KOH / g, 80 mg KOH / g to 220 mg KOH / g, 80 mg KOH / g to 210 mg KOH / g, 80 mg KOH / g to 200 mg KOH / g, 80 mg KOH / g to 190 mg KOH / g, 80 mg KOH / g to 180mg KOH / g, 80mg KOH / g to 170mg KOH / g, 80mg KOH / g to 150mg KOH / g, 80mg KOH / g to 140mg KOH / g, 80mg KOH / g to 130mg KOH / g, 80mg KOH / g to 110mg KOH / g, 80mg KOH / g to 100mg KOH / g, 90mg KOH / g to 250mg KOH / g, 90mg KOH / g to 240mg KOH / g, 90mg KOH / g to 230mg KOH / g, 90mg KOH / g to 220mg KOH / g, 90mg KOH / g to 210mg KOH / g, 90mg KOH / g to 200mg KOH / g, 90mg KOH / g to 190mg KOH / g, 90mg KOH / g to 180 mg KOH / g, 90 mg KOH / g to 170 mg KOH / g, 90 mg KOH / g to 150 mg KOH / g, 90 mg KOH / g to 140 mg KOH / g, 90 mg KOH / g to 130 mg KOH / g, 90 mg KOH / g to 110 mg KOH / g, 90 mg KOH / g to 100 mg KOH / g. Other ranges are also contemplated.

[0012] In many embodiments, the acrylic resin has a number average molecular weight (Mn) of 1000 to 7000. The number average molecular weight (Mn) can be measured by NMR or GPC with reference to ASTM D5296-19. In other embodiments, the Mn of the acrylic resin described herein may be, for example, in the following ranges: 1000 to 6500, 1000 to 6000, 1000 to 5500, 1000 to 5000, 1000 to 4000, 1500 to 7000, 1500 to 6500, 1500 to 6000, 1500 to 5500, 1500 to 5000, 1500 to 4000, 2000 to 7000, 2000 to 6500. , 2000 to 6000, 2000 to 5500, 2000 to 5000, 2000 to 4000, 2500 to 7000, 2500 to 6500, 2500 to 6000, 2500 to 5500, 2500 to 5000, 2500 to 4000, 3000 to 7000, 3000 to 6500, 3000 to 6000, 3000 to 5500, 3000 to 5000, and 3000 to 4000. In a particular embodiment, the acrylic resin has an Mn of 2000 to 6000. Other Mn values are also contemplated.

[0013] In many embodiments, the Tg of the acrylic resin is between 10°C and 90°C. The Tg described herein is measured by differential scanning calorimetry (DSC) using ASTM D6604-00. In other embodiments, the Tg of the acrylic resin described herein may be, for example, in the following ranges: 10°C to 85°C, 10°C to 80°C, 10°C to 75°C, 10°C to 70°C, 10°C to 65°C, 10°C to 60°C, 15°C and 90°C, 15°C to 85°C, 15°C to 80°C, 15°C to 75°C, 15°C to 70°C, 15°C to 65°C, 15°C to 60°C, 20°C to 90°C , 20℃ to 85℃, 20℃ to 80℃, 20℃ to 75℃, 20℃ to 70℃, 20℃ to 65℃, 20℃ to 60℃, 25℃ and 90℃, 25℃ to 85℃, 25℃ to 80℃, 25℃ to 75℃, 25℃ to 20℃, 25℃ to 65℃, 25℃ to 60℃, 30℃ to 85℃, 30℃ to 80℃, 30℃ to 75℃, 30℃ to 70℃, 30℃ to 65℃, 30℃ to 60℃, 35℃ and 90℃, 35℃ to 85℃, 35℃ to 80℃, 35℃ to 75℃, 35℃ to 70℃, 35℃ to 65℃, 35℃ to 60℃, 40℃ and 90℃, 40℃ to 85℃, 40℃ to 80℃, 40℃ to 75℃, 40℃ to 70℃, 40℃ to 65℃, 40℃ to 60℃, 45℃ and 90℃, 45℃ to 85℃, 45℃ to 80℃, ℃, 5°C to 75°C, 45°C to 70°C, 45°C to 65°C, 45°C to 60°C, 50°C and 90°C, 50°C to 85°C, 50°C to 80°C, 50°C to 75°C, 50°C to 70°C, 50°C to 65°C, 50°C to 60°C, 55°C and 90°C, 55°C to 85°C, 55°C to 80°C, 55°C to 75°C, 55°C to 70°C, 55°C to 65°C, and 55°C to 60°C. In one embodiment, the Tg of the acrylic resin is between 40°C and 80°C.

[0014] In many embodiments, the acrylic resin described herein comprises at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted to at least one hydroxyl group of the acrylic resin, and the at least one epoxy silane oligomer is 0.1 wt % to 30 wt % of the acrylic resin. In other embodiments, the epoxy silane oligomers described herein may be, for example, in the following ranges: 0.1 wt % to 25 wt %, 0.1 wt % to 20 wt %, 0.1 wt % to 15 wt %, 0.1 wt % to 10 wt %, 0.1 wt % to 5 wt %, 0.5 wt % to 30 wt %, 0.5 wt % to 25 wt %, 0.5 wt % to 20 wt %, 0.5 wt % to 15 wt %, 0.5 wt % to 10 wt %, 0.5 wt % to 5 wt %, 1 wt % to 30 wt %, 1 wt % to 25 wt %, 1 wt % to 20 wt %, 1 wt % to 15 wt %, 1 wt % to 10 wt %, 1 wt % to 5 wt %, 2 wt % to 30 wt %, 2 wt % to 25 wt %, 2 % to 30 wt %, 10 wt % to 25 wt %, 15 wt % to 20 wt %, 2 wt % to 15 wt %, 2 wt % to 10 wt %, 2 wt % to 5 wt %, 5 wt % to 30 wt %, 5 wt % to 25 wt %, 5 wt % to 20 wt %, 5 wt % to 15 wt %, 5 wt % to 10 wt %, 7 wt % to 30 wt %, 7 wt % to 25 wt %, 7 wt % to 20 wt %, 7 wt % to 15 wt %, 7 wt % to 10 wt %, 10 wt % to 30 wt %, 10 wt % to 25 wt %, 10 wt % to 20 wt %, 10 wt % to 15 wt %, 15 wt % to 30 wt %, 15 wt % to 25 wt %, 15 wt % to 20 wt %, 20 wt % to 30 wt %, and 20 wt % to 25 wt %. Other ranges are also contemplated.

[0015] In many embodiments, the at least one epoxy silane oligomer has a number average molecular weight (Mn) in the range of 400 to 2000. The number average molecular weight (Mn) can be measured by NMR or GPC with reference to ASTM D5296-19. In other embodiments, the epoxy silane oligomers described herein may be, for example, in the following ranges: 400 to 1800, 400 to 1500, 400 to 1300, 400 to 1200, 400 to 1000, 500 to 2000, 500 to 1800, 500 to 1500, 500 to 1300, 500 to 1200, 500 to 1000, 600 to 2000, 600 to 1800, 600 to 1500, 600 to 1300, 600 to 1200, 600 to 1000, 700 to 2000, 700 to 1800, 700 to 1 Other ranges are also contemplated.

[0016] In many embodiments, the ureido functionality of the acrylic resin comprises a ureido monomer having a (meth)acrylate group and a cyclic ureido group. In some embodiments, the ureido monomer comprises Structure I, Structure II, or a combination thereof.

[0017]

[0018] In some embodiments, the urea-based monomer is present in an amount of 0.1 to 10.0 wt % of the total monomer weight of the acrylic resin. In another embodiment, the urea-based monomer is present in an amount of 1.0 to 8.0 wt % of the total monomer weight of the acrylic resin. In yet another embodiment, the urea-based monomer is present in an amount of 1.0 to 5.0 wt % of the total monomer weight of the acrylic resin. In other embodiments, the urea-based monomers described herein may be, for example, in the following ranges: 0.1 to 9.0 wt %, 0.1 to 8.0 wt %, 0.1 to 7.0 wt %, 0.1 to 6.0 wt %, 0.1 to 5.0 wt %, 0.1 to 4.0 wt %, 0.5 to 10.0 wt %, 0.5 to 9.0 wt %, 0.5 to 8.0 wt %, 0.5 to 7.0 wt %, 0.5 to 10.0 wt %. % to 6.0 wt%, 0.5 wt% to 5.0 wt%, 0.5 wt% to 4.0 wt%, 1.0 wt% to 10.0 wt%, 1.0 wt% to 9.0 wt%, 1.0 wt% to 8.0 wt%, 1.0 wt% to 7.0 wt%, 1.0 wt% to 6.0 wt%, 1.0 wt% to 4.0 wt%, 1.5 wt% to 10.0 wt%, 1.5 wt% to 9.0 wt%, 1.5 wt% to 8.0 wt%, 1.5 wt% to 7 %. 0 wt%, 1.5 wt% to 6.0 wt%, 1.5 wt% to 5.0 wt%, 1.5 wt% to 4.0 wt%, 2.0 wt% to 10.0 wt%, 2.0 wt% to 9.0 wt%, 2.0 wt% to 8.0 wt%, 2.0 wt% to 7.0 wt%, 2.0 wt% to 6.0 wt%, 2.0 wt% to 5.0 wt%, 2.0 wt% to 4.0 wt%, 2.5 wt% to 10.0 wt%, 2.5 wt% to 9.0 wt%. %, 2.5 wt % to 8.0 wt %, 2.5 wt % to 7.0 wt %, 2.5 wt % to 6.0 wt %, 2.5 wt % to 5.0 wt %, 2.5 wt % to 4.0 wt %, 3.0 wt % to 10.0 wt %, 3.0 wt % to 9.0 wt %, 3.0 wt % to 8.0 wt %, 3.0 wt % to 7.0 wt %, 3.0 wt % to 6.0 wt %, 3.0 wt % to 5.0 wt %, and 3.0 wt % to 4.0 wt %. Other ranges are contemplated.

[0019] In many embodiments, the epoxy silane monomer is a monomer present in an amount of 0.1 to 10.0 wt % based on the total monomer weight. In another embodiment, the epoxy silane monomer is a monomer present in an amount of 0.1 to 8.0 wt % based on the total monomer weight of the acrylic resin. In some embodiments, the epoxy silane monomer is a monomer present in an amount of 0.5 to 6.0 wt % based on the total monomer weight. In other embodiments, the epoxy silane monomers described herein may be, for example, in the following ranges: 0.1 to 9.0 wt %, 0.1 to 7.0 wt %, 0.1 to 6.0 wt %, 0.1 to 5.0 wt %, 0.1 to 4.0 wt %, 0.5 to 10.0 wt %, 0.5 to 9.0 wt %, 0.5 to 8.0 wt %, 0.5 to 7.0 wt %, 0.5 to 5.0 wt %. %, 0.5 wt% to 4.0 wt%, 1.0 wt% to 10.0 wt%, 1.0 wt% to 9.0 wt%, 1.0 wt% to 8.0 wt%, 1.0 wt% to 7.0 wt%, 1.0 wt% to 6.0 wt%, 1.0 wt% to 5.0 wt%, 1.0 wt% to 4.0 wt%, 1.5 wt% to 10.0 wt%, 1.5 wt% to 9.0 wt%, 1.5 wt% to 8.0 wt%, 1.5 wt% to 7.0 wt%, 1.5 wt% to 6.0 wt%, 1.5 wt% to 5.0 wt%, 1.5 wt% to 4.0 wt%, 2.0 wt% to 10.0 wt%, 2.0 wt% to 9.0 wt%, 2.0 wt% to 8.0 wt%, 2.0 wt% to 7.0 wt%, 2.0 wt% to 6.0 wt%, 2.0 wt% to 5.0 wt%, 2.0 wt% to 4.0 wt%, 2.5 wt% to 10.0 wt%, 2.5 wt% to 9.0 wt%, % to 8.0 wt%, 2.5 wt% to 7.0 wt%, 2.5 wt% to 6.0 wt%, 2.5 wt% to 5.0 wt%, 2.5 wt% to 4.0 wt%, 3.0 wt% to 10.0 wt%, 3.0 wt% to 9.0 wt%, 3.0 wt% to 8.0 wt%, 3.0 wt% to 7.0 wt%, 3.0 wt% to 6.0 wt%, 3.0 wt% to 5.0 wt%, and 3.0 wt% to 4.0 wt%. Other ranges are contemplated.

[0020] In some embodiments, at least one acrylic resin comprises styrene, methyl methacrylate, methacrylic acid, hydroxyethyl acrylate, acetoacetoxyethyl methacrylate, butyl acrylate, butyl methacrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n- / iso- / tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl methacrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, isobornyl (meth)acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, 2-(acetoacetoxy)ethyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, diacetone acrylamide, acrylamide, methacrylamide, hydroxymethyl (meth)acrylamide, styrene, α-methylstyrene, vinyltoluene, vinyl acetate, vinyl propionate, allyl methacrylate, or a combination thereof. Other acrylic resins are also contemplated.

[0021] In many embodiments, the acrylic resin described herein may include at least one silane epoxy oligomer. Silane epoxy functional oligomers can provide improved adhesion and crosslinking. In one embodiment, the silane epoxy oligomer may include 3-(2,3-glycidoxypropyl)triethoxysilane. In another embodiment, the silane epoxy oligomer may include 3-(2,3-glycidoxypropyl)methyldiethoxysilane, and in another embodiment, the silane epoxy oligomer may include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. In yet another embodiment, the silane epoxy oligomer may include 3-glycidyl-oxypropyl-trimethoxy-silane. In yet another embodiment, the silane epoxy oligomer includes 3-glycidyl-oxypropyl-methyldimethoxy-silane. In yet another embodiment, at least one silane epoxy oligomer comprises 3-(2,3-glycidoxypropyl)triethoxysilane, 3-(2,3-glycidoxypropyl)methyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidyl-oxypropyl-trimethoxy-silane, 3-glycidyl-oxypropyl-methyldimethoxy-silane, or a combination thereof. Other silane epoxy oligomers are contemplated. In one embodiment, the silane epoxy oligomer can be functionalized. In some embodiments, the silane epoxy oligomers described herein have an epoxy value (mol / 100g epoxy) of 0.20 to 1.00 as measured by ASTM D1652-11.In some embodiments, the epoxy value of the silane epoxy oligomer can be, for example, in the following ranges as measured by ASTM D1652-11: 0.20 to 0.95, 0.20 to 0.90, 0.20 to 0.85, 0.20 to 0.80, 0.20 to 0.75, 0.20 to 0.70, 0.20 to 0.65, 0.20 to 0.60, 0.20 to 0.55, 0.20 to 0.50, 0.20 to 0.45, 0.20 to 0.40, 0.20 to 0.35, 0.20 to 0.30, 0.30 to 1.00, 0.30 to 0.95, 0.30 to 0.90, 0.30 to 0.85, 0.30 to 0.80, 0.30 to 0.75, 0.30 to 0.70, 0.30 to 0.65, 0.30 to 0.60, 0.30 to 0.55, 0.30 to 0.50, 0.30 to 0.45, 0.35 to 1.00, 0.35 to 0.95, 0.35 to 0.90, 0 0.35 to 0.85, 0.35 to 0.80, 0.35 to 0.75, 0.35 to 0.70, 0.35 to 0.65, 0.35 to 0.60, 0.35 to 0.60, 0.35 to 0.55, 0.35 to 0.50, 0.40 to 1.00, 0.40 to 0.95, 0.40 to 0.90, 0.40 to 0.85, 0.40 to 0.80, 0.40 to 0.75, 0.40 to 0 0.70, 0.40 to 0.65, 0.40 to 0.60, 0.40 to 0.55, 0.40 to 0.50, 0.45 to 1.00, 0.45 to 0.95, 0.45 to 0.90, 0.45 to 0.85, 0.45 to 0.80, 0.45 to 0.75, 0.45 to 0.70, 0.45 to 0.65, 0.45 to 0.60, 0.45 to 0.55, and 0.45 to 0.50.

[0022] In some embodiments, at least one acid group of at least one acrylic resin is at least partially grafted to at least one epoxy silane oligomer. It is speculated that at least one hydroxyl group of the acrylic resin is grafted or partially grafted to at least one epoxy silane oligomer, and this grafting may provide unexpected benefits.

[0023] In addition, at least one acid group may have an acid number (calculated in mg KOH). Without being bound by theory, the acid number may be varied so that the coating properties can achieve desired properties. In some embodiments, the acid number (calculated in mg KOH) may be in the range of 2 to 30. In other embodiments, the acid numbers described herein may be, for example, in the ranges of 2 to 25, 2 to 22, 2 to 20, 2 to 18, 2 to 15, 2 to 13, 2 to 10, 2 to 8, 2 to 5, 5 to 30, 5 to 25, 5 to 22, 5 to 20, 5 to 18, 5 to 15, 5 to 13, 5 to 10, 5 to 8, 7 to 30, 7 to 25, 7 to 22, 7 to 2 0, 7-18, 7-15, 7-13, 7-10, 10-30, 10-25, 10-22, 10-20, 10-18, 10-15, 10-13, 12-30, 12-25, 12-22, 12-20, 12-18, 12-15, 15-30, 15-25, 15-22, 15-20, and 15-18. Other ranges are also contemplated.

[0024] Also disclosed is a method for preparing the acrylic resin described herein. The acrylic resin comprises at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted to at least one hydroxyl group of the acrylic resin; wherein the at least one hydroxyl group of the acrylic resin has at least one urea functional group; and wherein the at least one hydroxyl group of the acrylic resin has at least one acid group.

[0025] Also provided is a two-component coating system comprising: 1) a first part comprising at least one isocyanate; and 2) a second part comprising an acrylic resin disclosed herein, wherein the acrylic resin comprises at least one hydroxyl group and at least one epoxysilane oligomer; wherein the at least one hydroxyl group of the acrylic resin has a urea functional group.

[0026] In a two-component system, the first part may comprise at least one isocyanate such that when the isocyanate is combined with the second component described herein comprising hydroxyl groups, a polyurethane is formed. For a two-component coating system, the isocyanate may serve as a hardener for the system. The isocyanate-functional material may be selected from monofunctional isocyanates, difunctional isocyanates, trifunctional isocyanates, and polyfunctional isocyanates. Furthermore, the isocyanate-functional material may be (cyclo)aliphatic, araliphatic, or aromatic in nature. Representative isocyanates will have two or more isocyanate groups per molecule and may include aliphatic compounds such as ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 1,2-propylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, ethylene diisocyanate, and butylene diisocyanate; cycloalkylene compounds such as 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate and 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, and 1,2-cyclohexane diisocyanate; aromatic compounds such as m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4'-diphenyl diisocyanate, 1,5-naphthalene diisocyanate, and 1,4- Naphthalene diisocyanate; aliphatic-aromatic compounds such as 4,4'-xylylene diisocyanate, 2,4-toluene diisocyanate or 2,6-toluene diisocyanate or mixtures thereof, 4,4'-toluidine diisocyanate and 1,4-phenylenedimethyl isocyanate; nuclear-substituted aromatic compounds such as dianisidine diisocyanate, 4,4'-diphenyl ether diisocyanate and chlorodiphenylene diisocyanate; triisocyanates such as triphenylmethane-4,4',4"-triisocyanate, 1,3,5-triisocyanatebenzene and 2,4,6-triisocyanatetoluene; and tetraisocyanates such as 4,4'-diphenyl-dimethylmethane-2,2'-5,5'-tetraisocyanate; polymeric polyisocyanates such as toluene diisocyanate dimers and trimers, and various other polyisocyanates containing biuret, urethane and / or allophanate linkages.In addition, the isocyanate may be a hydrophobic organic polyisocyanate, including but not limited to: 1,6-diisocyanatohexane, isophorone diisocyanate, diphenylmethane diisocyanate, 4,4'-bis(isocyanatocyclohexyl)methane, 1,4-diisocyanatobutane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatohexane, Cyanato decane, 4,4-diisocyanato-cyclohexane, 2,4-hexahydrotoluene diisocyanate, 2,6-hexahydrotoluene diisocyanate, norbornane diisocyanate, 1,3-phenylenedimethyl isocyanate, 1,4-phenylenedimethyl isocyanate, 1-isocyanato-3-(isocyanatomethyl)-1-methylcyclohexane, m-α, α-α', α'-tetramethylxylene diisocyanate or a combination thereof. In some embodiments, the hydrophobic polyisocyanate may include biuret, polyurethane, uretdione and isocyanurate derivatives of the above-mentioned compounds. Typically, these products are liquid at ambient temperature and are commercially available on a wide range of markets. Particularly preferred isocyanate curing agents are triisocyanates and adducts. Examples thereof are 1,8-diisocyanato-4-(isocyanatomethyl)octane, an adduct of 3 moles of toluene diisocyanate with 1 mole of trimethylolpropane, an isocyanurate trimer of 1,6-diisocyanatohexane, an isocyanurate trimer of isophorone diisocyanate, a uretdione dimer of 1,6-diisocyanatohexane, a biuret trimer of 1,6-diisocyanatohexane, an adduct of 3 moles of meta-α,α-α',α'-tetramethylxylene diisocyanate with 1 mole of trimethylolpropane, and combinations thereof. Optionally, the isocyanate may comprise an organic hydrophilic polyisocyanate compound substituted with a nonionic group, such as the C1-C4 alkoxy polyoxyalkylene group described above. In some embodiments, 30% by weight of the nonionic group may be present on the total solid polyisocyanate compound, i.e., an organic hydrophobic and hydrophilic polyisocyanate. In other embodiments, 20% by weight of the nonionic groups may be present in the total solid polyisocyanate compound. In other embodiments, 15% by weight of the nonionic groups may be present in the total solid polyisocyanate compound. Combinations of monofunctional isocyanates, difunctional isocyanates, trifunctional isocyanates, and polyfunctional isocyanates are also contemplated. The isocyanates may be water-based, solvent-based, or a combination thereof.

[0027] In some methods, the isocyanate functional material can be packaged separately from the components including the above-mentioned polymer system and other optional components. Depending on the needs of a particular application, the curing component including the isocyanate functional material can also include one or more catalysts, solvents, non-reactive (non-reactive with isocyanate) additives, and combinations thereof.

[0028] The isocyanate functional material can be mixed into the second part comprising the acrylic resin described herein by any suitable technique. However, simple stirring is usually sufficient. Sometimes it may be useful to dilute the isocyanate functional material with an organic solvent such as butyl acetate or 1-methoxy-2-propyl acetate to reduce viscosity.

[0029] In many embodiments, the mixing ratio of isocyanate (NCO) and polyol (OH) can be calculated to maximize the performance of the two-component coating system described herein. The equivalent weights of both isocyanate (NCO) and polyol (OH) are calculated separately.

[0030] Equivalent weight (eq. wt.) is used to calculate how many grams of product are needed to produce one equivalent of reactive groups. For isocyanates, the reactive group is -N=C=O ("NCO"), the concentration of which is measured by weight percent NCO) and calculated as follows: Isocyanate equivalent weight (NCO EW) is calculated by dividing 4202 by the hydroxyl number:

[0031]

[0032] Similarly, the reactive group of a polyol is -OH (OH), and the hydroxyl value can be calculated. The hydroxyl value is determined using ASTM E222-65T. The hydroxyl equivalent weight (OH EW) is calculated by dividing 56100 by the hydroxyl value:

[0033]

[0034] The isocyanate equivalent weight and polyol equivalent weight calculated as shown above provide the equivalent weight of both NCO and OH values used to describe the NCO / OH ratio range. In many embodiments, the NCO / OH ratio (also known as the isocyanate index) is in the range of 1.01:1.00 to 1.30:1.00. In other embodiments, the NCO / OH ratio is in the range of 1.02:1.00 to 1.20:1.00. In other embodiments, the NCO / OH ratio can be, for example, in the following ranges: 1.01:1.00 to 1.25:1.00, 1.01:1.00 to 1.20:1.00, 1.01:1.00 to 1.15:1.00, 1.01:1.00 to 1.10:1.00, 1.02:1.00 to 1.30:1.00, 1.02:1.00 to 1.25:1.00, 1.02:1.00 to 1.15:1.00, 1.02:1.00 to 1.10:1.00, 1.03:1.00 to 1.30:1.00, 1.03:1.00 to 1.25:1.00, 1.03:1.00 to 1.20:1. 00, 1.03:1.00 to 1.10:1.00, 1.05:1.00 to 1.30:1.00, 1.05:1.00 to 1.25:1.00, 1.05:1.00 to 1.20:1.00, 1.05:1.00 to 1.15:1.00, 1.05:1.00 to 1.10:1.00, 1.07:1.00 to 1.30:1.00, 1.07:1.00 to 1.25:1.00, 1.07:1.00 to 1.20:1.00, 1.07:1.00 to 1.15:1.00, and 1.07:1.00 to 1.10:1.00.

[0035] Additionally, in many embodiments, the two-component coating systems described herein further comprise at least one of a thickener, a defoamer, a dispersant, a wetting agent, a flow agent, a catalyst, a solvent, an anti-dripping agent, an anti-corrosion agent, an anti-pop agent, an adhesion promoter, a pigment, a filler, a hardener, or a combination thereof.

[0036] In addition, the two-component coating systems described herein can be applied directly to the surface of a substrate. In many embodiments, the substrate comprises wood, metal, glass, plastic, paper, leather, fabric, ceramic, or any combination thereof. Other substrates are also contemplated.

[0037] Also disclosed is a method for preparing the two-component coating system disclosed herein. The two-component coating system comprises: 1) a first part comprising at least one isocyanate; and 2) a second part comprising an acrylic resin, wherein the acrylic resin comprises at least one hydroxyl group and at least one epoxy silane oligomer, and wherein at least one hydroxyl group of the acrylic resin has a urea functional group.

[0038] Examples and Tests

[0039] Example 1 Acrylic resin having only urea groups .

[0040] 1345 g of n-butyl acetate was placed in a clean 5000 mL flask equipped with a mechanical stirrer, an N2 inlet, and a reflux condenser. The flask was filled with N2 and heated to 115°C. All acrylic monomers (methyl methacrylate: 163.8 g; n-butyl methacrylate: 403.2 g; hydroxyethyl methacrylate: 588 g; isobornyl methacrylate: 672 g; methyl methacrylate: 189 g; N-(2-methacryloyloxyethyl)ethylene urea (MEEU): 63 g; methacrylic acid: 21 g) were added to one pot, and the initiator, t-amyl peroctoate: 132.3 g, was added to another pot. The monomer mixture and initiator were fed into the flask at 115°C over 4.0 hours. After the feeds, the reaction was held for 30 minutes. Then, 6.3 g of t-amyl peroctoate was added in one portion and held for 40 minutes. After holding, add another 6.3g of tert-amyl peroctoate and hold for 60 minutes. Cool the reaction to 90°C or below. Add 40g of n-butyl acetate to adjust the NVM of the resin. Filter the resin into a metal can. The non-volatile material of the resin solution is 61.0% and the Gardner viscosity is Z3 + .

[0041] Example 2 Acrylic resin containing urea groups and epoxy silane oligomer

[0042] 1295 g of n-butyl acetate was placed in a clean 5000 mL flask equipped with a mechanical stirrer, an N2 inlet, and a reflux condenser. The flask was filled with N2 and heated to 115°C. All acrylic monomers (methyl methacrylate: 163.8 g; n-butyl methacrylate: 403.2 g; hydroxyethyl methacrylate: 588 g; isobornyl methacrylate: 672 g; methyl methacrylate: 189 g; MEEU: 63 g; methacrylic acid: 21 g) were added to one pot, and the initiator, t-amyl peroctoate: 132.3 g, was added to another pot. At 115°C, the monomer mixture and initiator were fed into the flask over 4.0 hours. After the feeds, the reaction was held for 30 minutes. Then, 6.3 g of t-amyl peroctoate was added all at once and held for 40 minutes. After the hold, another 6.3 g of t-amyl peroctoate was added and held for 60 minutes. Cool the reaction mixture to 90°C or below. Add 42g of epoxy-functional silane oligomer and 50g of n-butyl acetate. Maintain mixing for 30 minutes. Adjust the NVM with 50g of n-butyl acetate. Then filter the resin product into a metal can. The resin solution has a non-volatile material of 60.7% and a Gardner viscosity of Z3. + .

[0043] Example 3 Acrylic resin containing urea groups and epoxy silane oligomer

[0044] 1235 g of n-butyl acetate was placed in a clean 5000 mL flask equipped with a mechanical stirrer, an N2 inlet, and a reflux condenser. The flask was filled with N2 and heated to 115°C. All acrylic monomers (methyl methacrylate: 156 g; n-butyl methacrylate: 384 g; hydroxyethyl methacrylate: 560 g; isobornyl methacrylate: 640 g; methyl methacrylate: 180 g; MEEU: 60 g; methacrylic acid: 20 g) were added to one tank, and the initiator, t-amyl peroctoate: 126 g, was added to another tank. At 115°C, the monomer mixture and initiator were fed into the flask over 4.0 hours. After the feeds, the reaction was held for 30 minutes. Then, 6.0 g of t-amyl peroctoate was added in one portion and held for 40 minutes. After the hold, another 6.0 g of t-amyl peroctoate was added and held for 60 minutes. Cool the reaction mixture to 90°C or below. Add 80g of an epoxy-functional silane oligomer and 80g of n-butyl acetate. Maintain mixing for 30 minutes. Adjust the NVM with 40g of n-butyl acetate. Filter the resin product into a metal can. The resin solution has a nonvolatile content of 61.2% and a Gardner viscosity of Z1-Z2.

[0045] Example 4 Paint Formulation

[0046] The paint consisted of Part A, Part B, and Part C as provided in Tables 1 through 3 below. Part A, or the base, was made from the acrylic resin prepared according to Examples 1 and 3 above. 31 g of the resin and 5.811 g of xylene were added to a metal pint can. All other coating ingredients in Part A, shown in Table 1 below, were dispersed sequentially into the resin solution. The compositions of Part B, or the hardener, and Part C, or the diluent, are listed in Tables 2 and 3, respectively. In this spray-ready paint, the mixing ratio of Part A:Part B:Part C was 6:1 + 30% by volume.

[0047] Table 1-Part A

[0048]

[0049] Table 2 - Part B

[0050] Element Weight (g) nBA (butanol) 24.8 Dioctyltin dilaurate (DOTL) 0.2 Aliphatic polyisocyanates 65.0 Alicyclic polyisocyanate isophorone diisocyanate (IPDI) 10.0 total 100

[0051] Table 3-Part C

[0052] Element Weight (g) nBA (butanol) 49.7 Xylene 50.3 total 100

[0053] The coatings were prepared by spraying the coating onto steel panels that had been sanded with P180 sandpaper and solvent-degreased to a dry layer thickness of approximately 80 microns, with two coats applied. The flash-off time between coats was 7 minutes at 20°C. Adhesion directly to steel was tested after 7 days using the GT cross-hatch test (2 mm between lines) according to DIN EN ISO 2409. The DTM adhesion results, expressed as % delamination after the test, are listed in Table 4 below. The results show that the first comparative example, which contains only urea groups, showed no adhesion to the substrate without a wash primer. However, the last two paint samples based on the present invention showed adhesion equal to or better than those with a wash primer.

[0054] Table 4

[0055]

[0056] In some embodiments, additional adhesion promoters can be incorporated into formulations containing the acrylic resins described herein to further improve the adhesion of the resins of the present invention on various substrates. A new formulation (shown in Table 4 above) was prepared by adding 1% to 5% of an adhesion promoter to Formulation #2. The DTM adhesion results listed in Table 5 below demonstrate that the resin systems described herein with the additional adhesion promoters provide improved adhesion on cold-rolled steel and aluminum.

[0057] Table 5

[0058]

[0059]

[0060] Implementation Plan

[0061] The following embodiments are contemplated.All combinations of features and embodiments are contemplated.

[0062] Embodiment 1: An acrylic resin comprising: at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted to at least one hydroxyl group of the acrylic resin; wherein the at least one hydroxyl group of the acrylic resin has at least one urea functional group; and wherein the at least one hydroxyl group of the acrylic resin has at least one acid group.

[0063] Embodiment 2: The embodiment according to embodiment 1, wherein the acrylic resin has a hydroxyl number of 50 mg KOH / g to 250 mg KOH / g as measured by ASTM D6342-12.

[0064] Embodiment 3: The embodiment according to any one of embodiments 1 to 2, wherein the acrylic resin has an Mn of 1000 to 7000 as measured by ASTM D5296-19.

[0065] Embodiment 4: The embodiment according to any one of embodiments 1 to 3, wherein the acrylic resin has a Tg between 10°C and 90°C as measured by differential scanning calorimetry (DSC) using ASTM D6604-00.

[0066] Embodiment 5: The embodiment according to any one of embodiments 1 to 4, wherein the at least one epoxy silane oligomer is 0.1% to 30% by weight of the acrylic resin.

[0067] Embodiment 6: The embodiment according to any one of embodiments 1 to 5, wherein the at least one epoxy silane oligomer has a number average molecular weight (Mn) of 400 to 2000 as measured by NMR or GPC ref. ASTM D5296-19.

[0068] Embodiment 7: The embodiment of any one of embodiments 1 to 6, wherein the at least one epoxy silane oligomer has an epoxy value (mol / 100 g epoxy) of 0.20 to 1.00 as measured by ASTM D1652-11.

[0069] Embodiment 8: The embodiment of any one of embodiments 1 to 7, wherein the ureido functional group comprises a ureido monomer having a (meth)acrylate group and a cyclic ureido group.

[0070] Embodiment 9: The embodiment according to embodiment 8, wherein the urea-based monomer comprises structure I, structure II, or a combination thereof.

[0071]

[0072] Embodiment 10: The embodiment of any one of embodiments 8 to 9, wherein the urea-based monomer is 0.1 wt% to 10.0 wt% of the monomer based on the total monomer weight.

[0073] Embodiment 11: The embodiment of any one of embodiments 1 to 10, wherein the epoxy silane monomer is 0.1 wt% to 10.0 wt% monomer based on the total monomer weight.

[0074] Embodiment 12: The embodiment according to any one of embodiments 1 to 11, wherein the at least one acrylic resin comprises styrene, methyl methacrylate, methacrylic acid, hydroxyethyl acrylate, acetoacetoxyethyl methacrylate, butyl acrylate, butyl methacrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n- / iso- / t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, hydroxyethyl methacrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, isobornyl (meth)acrylate, glycidyl methacrylate, 4-hydroxybutyl glycidyl acrylate, 2-(acetoacetoxy)ethyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, diacetone acrylamide, acrylamide, methacrylamide, hydroxymethyl (meth)acrylamide, styrene, α-methylstyrene, vinyltoluene, vinyl acetate, vinyl propionate, allyl methacrylate, or a combination thereof.

[0075] Embodiment 13: The embodiment according to any one of embodiments 1 to 12, wherein at least one acid group of the at least one acrylic resin is at least partially grafted to at least one epoxy silane oligomer.

[0076] Embodiment 14: The embodiment according to any one of embodiments 1 to 13, wherein the at least one silane epoxy oligomer comprises 3-(2,3-glycidoxypropyl)triethoxysilane, 3-(2,3-glycidoxypropyl)methyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidyl-oxypropyl-trimethoxy-silane, 3-glycidyl-oxypropyl-methyldimethoxy-silane, or a combination thereof.

[0077] Embodiment 15: A method for preparing the acrylic resin according to any one of Embodiments 1 to 14.

[0078] Embodiment 16: A two-component coating system comprising: 1) a first part comprising at least one isocyanate; and 2) a second part comprising the acrylic resin according to any one of Embodiments 1 to 18.

[0079] Embodiment 17: The embodiment of embodiment 16, wherein the NCO / OH ratio is in the range of 1.01:1.00 to 1.30:1.00.

[0080] Embodiment 18: According to any one of embodiments 16 to 17, the two-component coating system further comprises at least one of the following: a thickener, a defoamer, a dispersant, a wetting agent, a flow agent, a catalyst, a solvent, an anti-sagging agent, an anti-corrosion agent, an anti-popping agent, an adhesion promoter, a pigment, a filler, a hardener, or a combination thereof.

[0081] Embodiment 19: According to any one of embodiments 16 to 18, the two-component coating system is applied directly to the surface of a substrate, and wherein the substrate comprises wood, metal, glass, plastic, paper, leather, fabric, ceramic, or any combination thereof.

[0082] Embodiment 20: A method of preparing a two-component coating system according to any one of Embodiments 16 to 19.

[0083] The foregoing includes examples of the claimed subject matter. All details, as well as any modifications described in conjunction with the background and detailed description, will be readily apparent to those skilled in the art as falling within the spirit and scope of the claimed subject matter. Furthermore, it should be understood that aspects of the claimed subject matter, as well as aspects of the various embodiments and features described below and / or in the appended claims, may be combined or interchanged in whole or in part. In the foregoing descriptions of various embodiments, those embodiments that refer to another embodiment may be appropriately combined with other embodiments, as those skilled in the art will recognize. Furthermore, those skilled in the art will recognize that the foregoing descriptions are presented merely as examples and are not intended to limit the claimed subject matter, recognizing that many additional combinations and permutations of the claimed subject matter are possible. Of course, for the purposes of describing the claimed subject matter, it is not possible to describe every conceivable combination of components or methods, but those skilled in the art will recognize these. Accordingly, the claimed subject matter is intended to encompass all such changes, modifications, and variations that fall within the spirit and scope of the appended claims. Furthermore, to the extent the term "comprising" is used in the detailed description or claims, such term is intended to be inclusive in a manner similar to how the term "comprise" is interpreted as "comprising" when used as a transitional word in a claim.

Claims

1. An acrylic resin, comprising: at least one epoxy silane oligomer, wherein the epoxy silane oligomer is grafted onto at least one hydroxyl group of the acrylic resin; wherein said at least one hydroxyl group of said acrylic resin has at least one urea functional group; and wherein the at least one hydroxyl group of the acrylic resin has at least one acid group. 2 . The acrylic resin according to claim 1 , wherein the acrylic resin has a hydroxyl number of 50 to 250 mg KOH / g as measured by ASTM D6342-12.

3. The acrylic resin according to any one of claims 1 to 2, wherein the acrylic resin has an Mn of 1000 to 7000 as measured by ASTM D5296-19.

4. The acrylic resin according to any one of claims 1 to 3, wherein the acrylic resin has a Tg between 10°C and 90°C as measured by differential scanning calorimetry (DSC) using ASTM D6604-00.

5. The acrylic resin according to any one of claims 1 to 4, wherein the at least one epoxy silane oligomer is 0.1% to 30% by weight of the acrylic resin.

6. The acrylic resin according to any one of claims 1 to 5, wherein the at least one epoxysilane oligomer has a number average molecular weight (Mn) between 400 and 2000 as measured by NMR or GPC referring to ASTM D5296-19.

7. The acrylic resin according to any one of claims 1 to 6, wherein the at least one epoxy silane oligomer has an epoxy value (mol / 100 g epoxy) of 0.20 to 1.00 as measured by ASTM D1652-11. 8 . The acrylic resin according to claim 1 , wherein the ureido functional group comprises a ureido monomer having a (meth)acrylate group and a cyclic ureido group.

9. The acrylic resin according to embodiment 8, wherein the urea-based monomer comprises structure I, structure II, or a combination thereof 10 . The acrylic resin according to claim 8 , wherein the urea-based monomer is 0.1 to 10.0 wt % of the monomer based on the total monomer weight. 11 . The acrylic resin according to claim 1 , wherein the epoxy silane monomer is 0.1 to 10.0 wt % of the monomer based on the total monomer weight.

12. The acrylic resin according to any one of claims 1 to 11, wherein at least one acrylic resin comprises styrene, methyl methacrylate, methacrylic acid, hydroxyethyl acrylate, acetoacetoxyethyl methacrylate, butyl acrylate, butyl methacrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n- / iso- / tert-butyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate, hydroxybutyl(meth)acrylate, isobornyl(meth)acrylate, glycidyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate glycidyl ether, 2-(acetoacetoxy)ethyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, cyclohexyl(meth)acrylate, diacetoneacrylamide, acrylamide, methacrylamide, hydroxymethyl(meth)acrylamide, styrene, α-methylstyrene, vinyltoluene, vinyl acetate, vinyl propionate, allyl(methacrylate), or a combination thereof.

13. The acrylic resin according to any one of claims 1 to 12, wherein at least one acid group of the at least one acrylic resin is at least partially grafted to at least one epoxysilane oligomer.

14. The acrylic resin according to any one of claims 1 to 13, wherein the at least one silane epoxy oligomer comprises 3-(2,3-glycidoxypropyl)triethoxysilane, 3-(2,3-glycidoxypropyl)methyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidyloxypropyl-trimethoxy-silane, 3-glycidyloxypropyl-methyldimethoxy-silane, or a combination thereof.

15. A method for preparing the acrylic resin according to any one of claims 1 to 14.

16. A two-component polyurethane coating system, comprising: a first portion comprising at least one isocyanate; and A second part comprising the acrylic resin according to any one of claims 1 to 14.

17. The two-component coating system of claim 16, wherein the NCO / OH ratio is in the range of 1.01:1.00 to 1.30:1.

00.

18. The two-component coating system according to any one of claims 16 to 17, further comprising at least one of the following: a thickener, a defoamer, a dispersant, a wetting agent, a flow agent, a catalyst, a solvent, an anti-sagging agent, an anti-corrosion agent, an anti-popping agent, an adhesion promoter, a pigment, a filler, a hardener, or a combination thereof.

19. The two-component coating system according to any one of claims 16 to 18, which is applied directly to the surface of a substrate, wherein the substrate comprises wood, metal, glass, plastic, paper, leather, fabric, ceramic, or any combination thereof.

20. A method for preparing a two-component coating system according to any one of claims 16 to 19.

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