A UV-cured epoxy acrylate, its preparation method and application

Abstract

This invention discloses a UV epoxy acrylate, its preparation method, and its application. The raw materials include epoxy monomers and acrylic monomers. The epoxy monomers include at least one selected from 3-phenoxy-1,2-epoxypropane, 3-o-tolyloxy-1,2-epoxypropane, 3-benzyloxy-1,2-epoxypropane, and 3-p-tert-butylphenoxy-1,2-epoxypropane. The molecular weight of the UV epoxy acrylate is 150-200. This invention's low-viscosity, high-elongation UV epoxy acrylate exhibits good flexibility, high elongation, low viscosity, good adhesion, and good leveling properties, solving the defects of traditional UV epoxy acrylates such as poor flexibility, low elongation, and high brittleness.

Description

Technical Field

[0001] This invention belongs to the field of coating technology, specifically relating to a UV epoxy acrylate, its preparation method, and its application. Background Technology

[0002] UV epoxy acrylate is currently the most widely used and consumed UV resin in the UV curing coating industry. It is produced by esterification of epoxy resin or epoxy monomers and acrylic monomers. UV curing technology is a new type of coating that instantly cures into a solid at room temperature. It has the characteristics of high efficiency, environmental protection, energy saving, and high quality, and is widely used in paper, wood, plastics and other fields. Traditional UV epoxy acrylate contains white crystalline bisphenol A (bisphenol A) segments in its molecular structure, with a melting point of 156-158℃. Therefore, it has strong rigidity, hardness and chemical resistance. However, its cured film has poor flexibility, low elongation and high brittleness. At the same time, the viscosity of traditional UV epoxy acrylate is very high. Therefore, it is not suitable for use alone in some substrates that require flexibility or are easily deformable. Therefore, it is usually used in combination with flexible UV resins such as polyurethane acrylate and polyester acrylate, which leads to an increase in the paint manufacturing process, paint manufacturing time and paint manufacturing cost.

[0003] Therefore, preparing a low-viscosity, high-elongation UV epoxy acrylate is an urgent task. Summary of the Invention

[0004] The present invention aims to solve at least one of the technical problems existing in the prior art. To this end, the present invention proposes a UV epoxy acrylate that solves the defects of traditional UV epoxy acrylates, such as poor flexibility, low elongation, and high brittleness, improves the elongation of UV epoxy acrylate, and reduces the viscosity of UV coatings prepared from UV epoxy acrylate as raw material, making it suitable for some substrate fields that require high elongation and are easily deformable.

[0005] A second aspect of the present invention provides a method for preparing the above-mentioned UV epoxy acrylate.

[0006] A third aspect of the present invention provides the application of the above-mentioned UV epoxy acrylate in UV-curable coatings.

[0007] A fourth aspect of the present invention provides the application of the above-described UV-curable coatings in the field of decoration.

[0008] According to an embodiment of the first aspect of the present invention, a UV epoxy acrylate is provided, the raw materials for preparation including: epoxy monomers and acrylic monomers;

[0009] The epoxy monomer includes at least one of 3-phenoxy-1,2-epoxypropane, 3-o-tolyloxy-1,2-epoxypropane, 3-benzyloxy-1,2-epoxypropane and 3-p-tert-butylphenoxy-1,2-epoxypropane.

[0010] The UV epoxy acrylate has a molecular weight of 150-200.

[0011] The embodiments of the first aspect of the present invention have at least the following beneficial effects:

[0012] The UV epoxy acrylate of this invention, through the ether chain segments in its molecular structure, gives it high torsion and tensile properties. Furthermore, by screening several epoxy monomers and acrylic monomers from this invention and reacting them, the molecular weight of the product is maintained between 150 and 200, thus exhibiting low viscosity and high elongation. This overcomes the shortcomings of traditional UV epoxy acrylates, such as poor flexibility, low elongation, and high brittleness. In practical applications, the low viscosity improves leveling and pigment / filler wetting properties, reducing the use of reactive diluent monomers. UV coatings prepared using the UV epoxy acrylate of this invention as a raw material are suitable for substrates requiring good flexibility, high elongation, and easy deformation.

[0013] According to some embodiments of the present invention, the acrylic monomer includes at least one of acrylic acid and methacrylic acid.

[0014] According to some embodiments of the present invention, the raw materials for preparation include, by weight, 65.00 to 80.00 parts of epoxy monomer and 20.00 to 35.00 parts of acrylic monomer.

[0015] According to some preferred embodiments of the present invention, the raw materials for preparation include, by weight, 65.00 to 70.00 parts of epoxy monomer and 25.00 to 35.00 parts of acrylic monomer.

[0016] According to some preferred embodiments of the present invention, the raw materials for preparation include, by weight, 70.00 to 75.00 parts of epoxy monomer and 25.00 to 30.00 parts of acrylic monomer.

[0017] According to some embodiments of the present invention, the raw materials for preparation also include: a catalyst, an antioxidant, and a polymerization inhibitor.

[0018] According to some embodiments of the present invention, the raw materials for preparation, by weight, include: 65.00-80.00 parts of epoxy monomer, 20.00-35.00 parts of acrylic monomer, 0.10-0.50 parts of catalyst, 0.30-0.60 parts of antioxidant and 0.10-0.30 parts of polymerization inhibitor.

[0019] According to some preferred embodiments of the present invention, the raw materials for preparation, by weight, include: 65.00-70.00 parts of epoxy monomer, 25.00-35.00 parts of acrylic monomer, 0.10-0.50 parts of catalyst, 0.30-0.60 parts of antioxidant and 0.10-0.30 parts of polymerization inhibitor.

[0020] According to some preferred embodiments of the present invention, the raw materials for preparation, by weight, include: 70.00-75.00 parts of epoxy monomer, 25.00-30.00 parts of acrylic monomer, 0.10-0.50 parts of catalyst, 0.30-0.60 parts of antioxidant and 0.10-0.30 parts of polymerization inhibitor.

[0021] According to some preferred embodiments of the present invention, the raw materials for preparation, by weight, include: 70.00-75.00 parts of epoxy monomer, 25.00-30.00 parts of acrylic monomer, 0.10-0.50 parts of catalyst, 0.30-0.60 parts of antioxidant and 0.10-0.30 parts of polymerization inhibitor.

[0022] According to some embodiments of the present invention, the catalyst comprises at least one selected from triethylamine, triphenylphosphine, and benzyltriethylammonium chloride.

[0023] According to some embodiments of the present invention, the antioxidant includes at least one of hypophosphite and triphenyl phosphite.

[0024] According to some embodiments of the present invention, the polymerization inhibitor includes at least one of hydroquinone, p-hydroxyanisole, and 2,6-di-tert-butyl-p-cresol.

[0025] According to an embodiment of a second aspect of the present invention, a method for preparing UV epoxy acrylate is provided, comprising the step of mixing and reacting the raw materials for preparing the UV epoxy acrylate until the acid value is below 4 mg KOH / g.

[0026] According to some preferred embodiments of the present invention, the preparation method of the UV epoxy acrylate includes sequentially adding epoxy monomer, acrylic monomer, antioxidant, and polymerization inhibitor to a reaction vessel, passing a protective gas, stirring for 5 minutes, adding a catalyst, heating to 90-100°C for 1 hour over 2-3 hours, then heating to 110-115°C for 3 hours over another hour, controlling the acid value to below 4 mg KOH / g, cooling to 70-80°C, stirring evenly, and then filtering out of the vessel.

[0027] According to some embodiments of the present invention, the protective gas includes at least one of oxygen and air.

[0028] According to an embodiment of a third aspect of the present invention, the application of the UV epoxy acrylate in UV-curable coatings is proposed.

[0029] According to an embodiment of the fourth aspect of the present invention, the application of the UV-curable coating in the field of decoration is proposed.

[0030] According to some embodiments of the present invention, the decorative field includes the substrate decoration field.

[0031] According to some embodiments of the present invention, the substrate includes one of cabinet doors, display cases, and wooden doors. Detailed Implementation

[0032] The following will describe the concept and technical effects of the present invention clearly and completely with reference to embodiments, so as to fully understand the purpose, features and effects of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, not all of them. Other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are all within the scope of protection of the present invention. All raw materials used in the present invention are commercially available.

[0033] Example 1

[0034] This embodiment provides a low-viscosity, high-elongation UV epoxy acrylate and its preparation method, wherein the raw materials and mass ratios are as follows:

[0035]

[0036] UV epoxy acrylate is prepared by the following steps:

[0037] After inspecting the equipment and preparing the raw materials, add 3-phenoxy-1,2-epoxypropane, acrylic acid, hypophosphite, and hydroquinone sequentially to the reactor. Purge with protective air and stir for 5 minutes. Then add benzyltriethylammonium chloride. Increase the temperature to 90-100℃ over 2-3 hours and react for 1 hour. Then increase the temperature to 110-115℃ over another hour and react for 3 hours. Maintain the acid value until it falls below 4 mg KOH / g. Reduce the temperature to 70-80℃, stir thoroughly, and filter out of the reactor. The molecular weight of the UV epoxy acrylate is between 150 and 200.

[0038] Example 2

[0039] This embodiment provides a low-viscosity, high-elongation UV epoxy acrylate and its preparation method, wherein the raw materials and mass ratios are as follows:

[0040]

[0041] UV epoxy acrylate is prepared by the following steps:

[0042] After checking the equipment and preparing the raw materials, add 3-phenoxy-1,2-epoxypropane, acrylic acid, hypophosphite, and hydroquinone to the reactor in sequence. Purge with protective air and stir for 5 minutes. Then add benzyltriethylammonium chloride. Heat to 90-100℃ for 2-3 hours and react for 1 hour. Then heat to 110-115℃ for 1 hour and react for 3 hours. Control the acid value to below 4 mg KOH / g, cool to 70-80℃, stir evenly, and filter out of the reactor.

[0043] The molecular weight of UV epoxy acrylate is between 150 and 200.

[0044] Example 3

[0045] This embodiment provides a low-viscosity, high-elongation UV epoxy acrylate and its preparation method, wherein the raw materials and mass ratios are as follows:

[0046]

[0047] UV epoxy acrylate is prepared by the following steps:

[0048] After inspecting the equipment and preparing the raw materials, add 3-benzyloxy-1,2-epoxypropane, methacrylic acid, hypophosphite, and p-hydroxyanisole to the reactor in sequence. Purge with protective air and stir for 5 minutes. Then add benzyltriethylammonium chloride. Heat to 90-100°C for 1 hour over 2-3 hours, then heat to 110-115°C for another hour and react for 3 hours. Maintain the acid value until it falls below 4 mg KOH / g, then cool to 70-80°C. After thorough stirring, filter the mixture. The molecular weight of the UV epoxy acrylate is between 150 and 200.

[0049] Example 4

[0050] This embodiment provides a low-viscosity, high-elongation UV epoxy acrylate and its preparation method, wherein the raw materials and mass ratios are as follows:

[0051]

[0052] UV epoxy acrylate is prepared by the following steps:

[0053] After inspecting the equipment and preparing the raw materials, add 3-benzyloxy-1,2-epoxypropane, 3-phenoxy-1,2-epoxypropane, acrylic acid, hypophosphite, and p-hydroxyanisole to the reactor in sequence. Purge with protective air, stir for 5 minutes, then add triphenylphosphine. Increase the temperature to 90-100℃ and react for 1 hour over 2-3 hours, then increase the temperature to 110-115℃ and react for 3 hours over another hour. Maintain the acid value until it falls below 4 mg KOH / g, then cool to 70-80℃, stir thoroughly, and filter out of the reactor. The molecular weight of the UV-cured epoxy acrylate is between 150 and 200.

[0054] Comparative Example 1

[0055] This comparative example provides a UV epoxy acrylate, with the same raw materials and mass ratio as in Example 1, except that 3-phenoxy-1,2-epoxypropane is replaced with an equal amount of liquid epoxy resin E-44, while the other conditions are the same.

[0056] Comparative Example 2

[0057] This comparative example provides a UV epoxy acrylate, with the same raw materials and mass ratio as in Example 1, except that 3-o-tolyloxy-1,2-epoxypropane is replaced with an equal amount of liquid epoxy resin E-51, while the other conditions are the same.

[0058] Test Example 1

[0059] The basic properties of the low-viscosity, high-elongation UV epoxy acrylate of this invention were tested in accordance with relevant national standards, and the test results are shown in Table 1.

[0060] Table 1. Performance testing of UV-cured epoxy acrylates

[0061]

[0062] As can be seen from the viscosity data in Table 1, the viscosity of the low-viscosity, high-elongation UV epoxy acrylate is significantly lower than that of the conventional UV epoxy acrylate in the comparison, while the other indicators are all within the acceptable range.

[0063] Test Example 2

[0064] The low-viscosity, high-elongation UV epoxy acrylate obtained by the present invention was used to prepare a UV spray matte clear topcoat. The formulation of the topcoat is shown in Table 2. Formulation 1 is a topcoat prepared using the UV epoxy acrylate prepared in Example 1 as raw material, and Formulation 2 is a topcoat prepared using the UV epoxy acrylate prepared in Comparative Examples 1, 2, 3, and 4 as raw material.

[0065] Table 2: UV Spraying Matte Clear Topcoat Formulation

[0066]

[0067] The topcoat obtained in Table 2 was tested according to relevant national standards, and the test results are shown in Table 3.

[0068] Table 3. Topcoat Performance Test

[0069]

[0070]

[0071] As can be seen from Table 3, the UV spray matte clear topcoat formulation prepared by the low viscosity and high elongation UV epoxy acrylate of the present invention has better leveling and wetting properties, the low viscosity makes it easier to spray and apply, and the excellent elongation is more suitable for use on easily deformable substrates, thus having a very broad application prospect.

[0072] The foregoing has shown and described the basic principles, main features, and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The embodiments and descriptions in the specification are merely illustrative of the principles of the invention. Various changes and modifications can be made to the invention without departing from its spirit and scope, and all such changes and modifications fall within the scope of the claims. The scope of protection of this invention is defined by the appended claims and their equivalents.

Claims

1. A UV-cured epoxy acrylate, characterized in that, The raw materials, by weight, consist of 65.00–80.00 parts of epoxy monomer, 20.00–35.00 parts of acrylic monomer, 0.10–0.50 parts of catalyst, 0.30–0.60 parts of antioxidant, and 0.10–0.30 parts of polymerization inhibitor; wherein the epoxy monomer is 3-phenoxy-1,2-epoxypropane, or 3-o-tolyloxy-1,2-epoxypropane, or 3-benzyloxy-1,2-epoxypropane, or 3-benzyloxy-1,2-epoxypropane and 3-phenoxy-1,2-epoxypropane. The molecular weight of the UV epoxy acrylate is 150~200; The method for preparing the UV epoxy acrylate includes the step of mixing and reacting the raw materials for preparing the UV epoxy acrylate until the acid value is below 4 mg KOH / g.

2. The UV-cured epoxy acrylate according to claim 1, characterized in that, The acrylic monomers include at least one of acrylic acid and methacrylic acid.

3. The UV-cured epoxy acrylate according to claim 1, characterized in that, The catalyst includes at least one of triethylamine, triphenylphosphine, and benzyltriethylammonium chloride.

4. The UV-cured epoxy acrylate according to claim 1, characterized in that, The antioxidant includes at least one of hypophosphite and triphenyl phosphite.

5. The UV-cured epoxy acrylate according to claim 1, characterized in that, The polymerization inhibitor includes at least one of hydroquinone, p-hydroxyanisole, and 2,6-di-tert-butyl-p-cresol.

6. A method for preparing UV-cured epoxy acrylate as described in any one of claims 1 to 5, characterized in that, The process includes the step of mixing and reacting the raw materials for the preparation of the UV epoxy acrylate until the acid value reaches below 4 mg KOH / g.

7. A UV-curable coating, characterized in that, The raw materials for preparing the UV-curable coating include the UV epoxy acrylate as described in any one of claims 1 to 5.

8. The application of a UV-curable coating as described in claim 7 in the field of decoration.

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