Search

JP-2026076336-A - Composition, cured product, laminate, and method for producing the cured product

JP2026076336AJP 2026076336 AJP2026076336 AJP 2026076336AJP-2026076336-A

Abstract

[Problem] To provide a curable composition for improving adhesion between an inorganic coating material and a resin substrate, a cured product with excellent appearance, adhesion, and durability, a method for producing the same, and a laminate having a cured product layer with excellent appearance, adhesion, and durability. [Solution] A curable composition comprising a monomer (X) having one or more selected from the group consisting of alkyl groups having 4 or more carbon atoms, fluorine atoms, and silicon atoms, and a copolymer (A) having a monomer (Y) having a functional group represented by the following chemical formula (1). -R 1 -M(R 2 ) r (OR 3 ) m-r ...(1) (However, M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta, R1 represents a hydrocarbon group having 1 to 5 carbon atoms, and R2 represents an alkyl group having 1 to 5 carbon atoms, or a group having 2 carbon atoms) R represents an alkenyl group or aryl group with 5 carbon atoms, R3 represents an alkyl group with 1 to 5 carbon atoms, an alkenyl group, aryl group, or acyl group or hydrogen with 2 to 5 carbon atoms, m represents an integer from 3 to 4 depending on M, r represents an integer from 0 to 3, if r is 2 or more, the r R2s may be different from each other, and if m-r is 2 or more, the (m-r) R3s may be different from each other. [Selection Diagram] None

Inventors

  • 真田 美希
  • 佐藤 嘉秀
  • 江口 晃生

Assignees

  • 三菱ケミカル株式会社

Dates

Publication Date
20260511
Application Date
20260217

Claims (9)

  1. A monomer (X) having one or more elements selected from the group consisting of alkyl groups with four or more carbon atoms, fluorine atoms, and silicon atoms, and a monomer (Y) having a functional group represented by the following chemical formula (1). A curable composition comprising a copolymer (A) having ). -R 1 -M(R 2 ) r (OR 3 ) m-r ...(1) (However, M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta, R1 represents a hydrocarbon group having 1 to 5 carbon atoms, and R2 represents an alkyl group having 1 to 5 carbon atoms, or a group having 2 carbon atoms) R represents an alkenyl group or aryl group with 5 carbon atoms, R3 represents an alkyl group with 1 to 5 carbon atoms, an alkenyl group with 2 to 5 carbon atoms, an aryl group, an acyl group, or hydrogen, m represents an integer from 3 to 4 depending on M, r represents an integer from 0 to 3, if r is 2 or more, the r R2s may be different from each other, and if m-r is 2 or more, the (m-r) R3s may be different from each other.
  2. The curable composition according to claim 1, comprising in the copolymer (A) a monomer (Z) having at least one crosslinkable functional group selected from an aromatic ketone group, a vinyl ether group, an epoxy group, and a (meth)acryloyl group, a hydroxyl group, and an isocyanate group.
  3. The curable composition according to claim 1 to 2, wherein the (X) component contained in the copolymer (A) is an alkyl group having 4 or more carbon atoms.
  4. The curable composition according to any one of claims 1 to 3, wherein the (Z) component contained in the copolymer (A) is an aromatic ketone group or a (meth)acryloyl group.
  5. The copolymer (A) contains 10 to 70% by mass of component (X) and 1% by mass of component (Y). A curable composition according to any one of claims 1 to 4, wherein the (Z) component is in the range of 0 to 90% by mass and 0 to 80% by mass.
  6. A cured film product of a curable composition according to any one of claims 1 to 5.
  7. A method for producing a cured product, comprising curing the curable composition according to any one of claims 1 to 5 by irradiating or heating the curable composition with an active energy ray.
  8. A laminate comprising a substrate, a primer layer provided on the substrate, and a topcoat layer provided on the primer layer, wherein the primer layer contains a copolymer (A) comprising a monomer (X) having one or more selected from the group consisting of alkyl groups having 4 or more carbon atoms, fluorine atoms, and silicon atoms, and a monomer (Y) having a functional group represented by the following chemical formula (1), and the topcoat layer is an inorganic coating layer. -R 1 -M(R 2 ) r (OR 3 ) m-r ...(1) (However, M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta, R1 represents a hydrocarbon group having 1 to 5 carbon atoms, R2 represents an alkyl group having 1 to 5 carbon atoms, or a group having 2 to 5 carbon atoms) R represents an alkenyl group or aryl group with 5 carbon atoms, where R3 is an alkyl group with 1 to 5 carbon atoms, or a group with 2 carbon atoms. ~5 represents an alkenyl group, aryl group, acyl group, or hydrogen, and m is 3 corresponding to M. R represents an integer between 4 and 4, r represents an integer between 0 and 3, and if r is 2 or greater, the r R2 elements may be distinct from each other, and if m-r is 2 or greater, the (m-r) R3 elements may be distinct from each other.
  9. The inorganic coating layer contains 40 compounds made of alkoxysilane or its hydrolysis condensate. The laminate according to claim 8, comprising a mass percentage or more.

Description

This invention relates to a composition, a cured product, a laminate, and a method for producing the cured product. Resin materials such as polycarbonate are lightweight and have a lower specific gravity compared to inorganic glass, are easy to process, and are impact-resistant. These characteristics make them suitable for a wide variety of components, including those for vehicles. However, resin materials also have drawbacks, such as being easily scratched, losing gloss and transparency, being susceptible to organic solvents, and having poor weather resistance (e.g., photostability against ultraviolet rays) and heat resistance. Automotive windows, for example, are often exposed to sunlight for extended periods. Therefore, when using resin materials in automotive components, it is necessary to provide the resin material with abrasion resistance and weather resistance by coating the surface with a protective layer. Coating agents primarily made from inorganic raw materials have a silicon dioxide backbone and can produce coatings with good weather resistance and scratch resistance. However, problems have been associated with crack formation due to temperature changes and poor adhesion to organic materials such as painted surfaces and resin substrates. A conventional technique for applying inorganic coating agents to resin materials is known, which involves a laminate comprising a resin substrate, an intermediate layer disposed on the surface of the resin substrate, and a silicon oxide layer disposed on the surface of the intermediate layer. Patent Document 1 proposes that the intermediate layer is made by curing a composition containing a Si-free compound containing (meth)acrylic groups and a siloxane compound containing (meth)acrylic groups, and that the adhesion is improved by making the Si concentration on the silicon oxide layer side of the intermediate layer higher than that on the resin substrate side. Japanese Patent Publication No. 2019-18449 The embodiments of the present invention will be described in detail below, but the following description is merely one example of an embodiment of the present invention, and the present invention is not limited to the following description unless it exceeds the gist of the invention. In this specification, when the expression "~" is used, it shall be used to include the numerical value or physical property value before and after it. Also, in this invention, when the expression "(meth)acrylic" is used, it shall mean either or both "acrylic" and "methacrylic". The same applies to "(meth)acrylate", "(meth)acryloyl", etc. [Composition] A curable composition according to one aspect of the present invention (hereinafter also referred to as "this composition") comprises a copolymer (A) containing a monomer (X) having one or more selected from the group consisting of alkyl groups having 4 or more carbon atoms, fluorine atoms, and silicon atoms, and a monomer (Y) having a functional group represented by the following chemical formula (1). This composition may further contain resin components as needed. This composition may further contain ultraviolet absorbers and light stabilizers, if necessary. This composition may further contain a diluent, if necessary. This composition may, if necessary, further contain other components not mentioned above, as long as they do not impair the effects of the present invention. <Copolymer A> The copolymer (A) may have units based on monomer (X), units based on monomer (Y), and further units based on monomer (Z) and monomer (V). <Monomer X> The monomer (X) is a compound having one or more elements selected from the group consisting of alkyl groups having four or more carbon atoms, fluorine atoms, and silicon atoms, and a radical polymerizable group. If monomer (X) is a low-surface-tension monomer and copolymer (A) has units based on monomer (X), then when a coating film of the curable polymer composition is formed, copolymer (A) is more likely to segregate to the surface side of the coating film. If copolymer (A), which has reactive functional groups with the inorganic coating layer, segregates to the surface side of the coating film, the number of reaction sites with the inorganic coating layer applied on top increases, improving adhesion. Furthermore, because functional groups can be efficiently segregated to the surface side, the amount of compound added can be reduced, especially for compounds that have poor compatibility with components in the curable polymer, and the loss of physical properties of the entire composition is suppressed. Examples of monomers (X) include compounds having one or more elements selected from the group consisting of alkyl groups with four or more carbon atoms, fluorine atoms, or silicon atoms, and a radical polymerizable group. Alkyl groups having four or more carbon atoms may be linear, branched, or cyclic. Cyclic alkyl groups may be monocyclic or polycyclic. From the viewpoint of more effectively segrega