KR-20260063864-A - Acrylate monomer, and UV and LED curable ink compositions comprising the same

Abstract

The present invention relates to an acrylate monomer represented by the following chemical formula 1 and a composition for UV and LED curable ink containing the same. The acrylate monomer according to the present invention has a high purity of 95% or more, has low viscosity characteristics by including an aliphatic alkyl group in its chain, and has the effect of improving the curing speed when included in a UV and LED curable composition. Chemical formula 1

Inventors

• 정정설
• 이재현
• 권도현

Assignees

• 재단법인 한국화학융합시험연구원

Dates

Publication Date

20260507

Application Date

20241031

Claims (6)

1. Acrylate monomer represented by the following chemical formula 1: Chemical formula 1 In the above chemical formula 1, R1, R2, R3, and R5 are the same or different from each other and are each a hydroxyl group; a carboxyl group; an ether group; an ester group; a C1 to C10 alkyl group; or any one selected from ethylene glycol containing an acrylate selected from ethylene glycol acrylate, diethylene glycol acrylate, triethylene glycol acrylate, and tetraethylene glycol acrylate. R4 is any one selected from a hydroxyl group, a carboxyl group, an ether group, and an ester group, and n is 1 to 15.
2. In Paragraph 1, The above acrylate monomer is an acrylate monomer having a weight-average molecular weight of 500 to 1,000 g/mol, a purity of 95% or more, and a viscosity of 80 to 100 cps.
3. A method for preparing an acrylate monomer according to claim 1, comprising the step of reacting a compound represented by the following chemical formula 2 with a compound represented by the following chemical formula 3. Chemical formula 2 In the above chemical formula 2, R1, R2, and R3 are the same or different from each other and are each a hydroxyl group; a carboxyl group; an ether group; an ester group; a C1 to C10 alkyl group; or any one selected from ethylene glycol containing an acrylate selected from ethylene glycol acrylate, diethylene glycol acrylate, triethylene glycol acrylate, and tetraethylene glycol acrylate. Chemical formula 3 In the above chemical formula 3, X is a halogen atom or a carboxyl group, and R4 is any one selected from a hydroxyl group, a carboxyl group, an ether group, and an ester group, and R5 is the same as defined in Chemical Formula 1 above, and n is 1 to 15.
4. A composition for UV and LED curable ink comprising an acrylate monomer represented by the chemical formula 1 of claim 1.
5. In Paragraph 4, The above ink composition is: A composition for UV and LED curing ink comprising 40 to 60 weight% of an oligomer having a molecular weight (Mw) between 2,000 and 50,000, 5 to 15 weight% of a difunctional acrylate monomer represented by the above chemical formula 1, 10 to 20 weight% of a pigment, 5 to 15 weight% of an initiator, and 5 to 15 weight% of other additives and dispersants.
6. In Paragraph 4, A composition for UV and LED curing inks, wherein the acrylate monomer represented by the above chemical formula 1 is used alone as the acrylate monomer, or is mixed with a tetrafunctional acrylate monomer in a weight ratio of 5:5 to 3:7.

Description

Acrylate monomer, and UV and LED curable ink compositions comprising the same The present invention relates to an acrylate monomer and a composition for UV and LED curable inks containing the same, and more specifically, to a composition for UV and LED curable inks having a fast curing speed using a high-purity difunctional acrylate monomer containing an aliphatic alkyl group. LED-curing ink enables printing with lower power consumption compared to UV-curing ink and is advantageous for workplace and environmental preservation due to the absence of ozone generation. Consequently, demand is expected to expand globally, starting with a surge in demand in the Americas and Europe. Despite the various advantages of LED-curing low-transition inks, the reality is that significant challenges currently to be overcome are acting as obstacles to their industrial widespread adoption. In particular, the curing speed of the ink varies depending on the absorption wavelength of the colorant, resulting in a high defect rate. The curing speed slows down in the order of red, yellow, blue, and black, and curing defects can occur, especially with black ink, when printed at high concentrations. This phenomenon is attributed to the difficulty in applying optimal initiators due to the use of long-wavelength initiators in LED inks, as well as the lack of optimal formulation design during formulation design. The current situation in Korea is that the United States and Europe virtually monopolize most of the core source technologies related to LED low-transition offset inks, and Korea relies entirely on Japan for some of the core materials and related technologies for LED curing inks. In particular, regarding monomers and photoinitiators, which are most important for the expression of low-transition characteristics, there are no domestically developed products, technologies, or patents, making research and development necessary to strengthen the future development capabilities of the domestic ink industry. Although low-transfer inks are produced by environmentally conscious companies in Europe and the U.S., such as Sun Chemical and Flint, there is no domestic production or sales. Consequently, if these eco-friendly and energy-saving products enter the domestic market, existing ink manufacturers will inevitably suffer a major blow, and a trade deficit will be unavoidable; thus, the development of such product lines is urgent. As for prior art regarding monomers used in such UV-curing offset inks, Korean Patent Publication No. 2021-0008943 presents an inkjet printing ink composition characterized by containing alkylene oxide-modified dipentaerythritol (meth)acrylate. In addition, Korean Registered Patent 10-1215459 describes an inkjet ink composition for an etching resist containing a polymerizable monomer capable of polymerizing by an active energy beam, wherein the viscosity at 25°C is 3 50 mPa, and the polymerizable monomer is a polymerizable ester compound represented by general formula (I) among the total monomers. 30 mass% and a polymerizable phosphate ester compound 3 having a phosphate ester group and an ethylenic double bond group within the molecule 10 mass%, and a polyfunctional monomer having two or more ethylenic double bonds within the molecule and not having phosphate ester groups, wherein the amount of said ethylenic double bonds is 4 x 10⁻³ Polyfunctional monomer 10 of 8 x 10⁻³ mol/g 75 mass% and 10 monofunctional monomers having one ethylenetic double bond within the molecule and not having phosphate ester groups or carboxyl groups An inkjet ink composition for etching resist containing 75 mass% was presented. Meanwhile, currently used acrylate monomers contain acrylate groups of various lengths randomly, resulting in low purity. This can lead to reduced reliability of the monomer product, which in turn causes a decrease in the reliability of the final curable ink composition. Figures 1 and 2 are printing results printed using an ink composition prepared according to Example 2 of the present invention, respectively. The present invention will be described in more detail below. The terms used in this specification are for describing specific embodiments and are not intended to limit the invention. As used herein, the singular form may include the plural form unless the context clearly indicates otherwise. Additionally, as used herein, “comprise” and/or “comprising” specify the presence of the mentioned features, numbers, steps, actions, parts, elements, and/or groups thereof, and do not exclude the presence or addition of one or more other features, numbers, actions, parts, elements, and/or groups. The present invention relates to an acrylate monomer and a composition for UV and LED curable inks containing the same. 1. Acrylate monomer The acrylate monomer according to the present invention comprises a difunctional acrylate and may be represented by the following chemical formula 1. Chemical formula 1 In the above chemi