JP-7855947-B2 - Resin compositions, cured products, and articles

Inventors

• 山田 駿介
• 下野 智弘
• キム ヨンチャン

Assignees

• ＤＩＣ株式会社

Dates

Publication Date

20260511

Application Date

20220630

Claims (5)

1. An indane-based mixture comprising an indane ring-containing compound (A) having a structural unit represented by the following general formula (1a), wherein at least one of the terminal sites bonded to the structural unit is an alkenyl group, and an indane ring-containing compound (A1) having an aniline skeleton, Compound (B) having a polymerizable unsaturated group, A resin composition containing a photopolymerization initiator. (In the above general formula (1a), R 11 , R 12 , and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n 12 represents the number of repeating units.)
2. The resin composition according to claim 1, wherein the mass ratio of the solid content of the indan ring-containing compound (A) and the compound having a polymerizable unsaturated group (B) [(A)/(B)] is in the range of 1/100 to 100/100.
3. The indane ring-containing compound (A) is given by the following general formula (1b): (In the above general formula (1b), R 11 , R 12 , and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) Q11 , Q12 , L11 , and L12 each independently represent a single bond or an alkylene group having 1 to 8 carbon atoms. P11 and P12 each independently represent a hydrogen atom, a polar group, an alkyl group having 1 to 6 carbon atoms which may be substituted with the polar group, an alkenyl group having 2 to 10 carbon atoms, or the following general formula (2), M11 and M12 each independently represent a single bond or the following general formula (3): n 12 represents the average number of repeating units, while n 11 and n 13 independently represent values from 0 to 20. However, at least one of P11 and P12 is an alkenyl group having 2 to 10 carbon atoms. [In the above general formula (2), R 15 independently represents an amino group, a fluoroalkyl group, or an alkyl group having 1 to 3 carbon atoms, and n 2 represents an integer between 0 and 4.] [In the above general formula (3), R 16 independently represents an amino group, a fluoroalkyl group, or an alkyl group having 1 to 3 carbon atoms, and n 3 represents an integer between 0 and 4.] The resin composition according to claim 1 or 2, represented by the general formulas (2) and (3), wherein the asterisk (*) in the general formulas (2) and (3) represents bonding with other atoms.
4. A cured product of the resin composition according to claim 1 or 2.
5. An article characterized by having a coating film made of the cured product described in claim 4.

Description

This disclosure relates to resin compositions, cured products obtained from said resin compositions, and articles. In recent years, curable compositions, such as active energy ray-curable compositions that can be cured by active energy rays like ultraviolet light, and thermosetting compositions that can be cured by heat, have been widely used in fields such as inks, paints, coatings, adhesives, and optical components. In particular, since the above-mentioned coating agents require various properties depending on the application, including curability, heat resistance, and low dielectric properties, it is essential to manufacture them using appropriate materials that match these properties. In this regard, Patent Document 1 describes a material that tends to exhibit excellent low dielectric properties in the cured product. Patent Document 1 discloses a hydrocarbon resin made of a polyindane derivative having a predetermined indane skeleton, which has a low dielectric constant even without the introduction of pores and is suitable as an interlayer insulating film material. Japanese Patent Publication No. 2007-311732 Figure 1 shows the GPC chart of the indane ring-containing compound (A-1) obtained in Synthesis Example 1.Figure 2 shows the GPC chart of the indane ring-containing compound (A-2) obtained in synthesis example 2.Figure 3 shows the GPC chart of the indane ring-containing compound (A-3) obtained in synthesis example 3.Figure 4 shows the GPC chart of the indan ring-containing compound (A-4) obtained in synthesis example 4.Figure 5 shows the GPC chart of the indane ring-containing compound (A-5) obtained in synthesis example 5.Figure 6 shows the FD-MS chart of the indane ring-containing compound (A-1) obtained in Synthesis Example 1.Figure 7 shows the 13C -NMR chart of the indan ring-containing compound (A-1) obtained in Synthesis Example 1. The embodiments of this disclosure (hereinafter referred to as "these embodiments") will be described in detail below, but this disclosure is not limited to the following description and can be implemented in various modifications within the scope of its gist. Unless otherwise specified in this specification, the following terms may be applied: [term] In this specification, "reaction raw material" refers to a compound used to obtain a target compound by a chemical reaction such as combination or decomposition, and which partially constitutes the chemical structure of the target compound. Substances that act as aids to chemical reactions, such as solvents and catalysts, are excluded. In particular, in this specification, "reaction raw material" refers to a precursor for obtaining an indan ring-containing compound (A) (including a mixture containing one or more indan ring-containing compounds (A)) by a chemical reaction. In this specification, the "aromatic group" preferably has an aromatic ring having 3 to 30 carbon atoms, and more preferably has an aromatic ring having 4 to 26 carbon atoms. Furthermore, in this specification, the hydrogen atoms of the aromatic ring in the "aromatic group" may be substituted with substituents, such as alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, or halogen atoms. In addition, the "aromatic group" may include heteroaromatic compounds, and the -CH2- or -CH= atoms in the "aromatic group" may be substituted with -O-, -S-, or -N= such that they are not adjacent to each other. Examples of the aromatic rings include monocyclic aromatic rings, fused aromatic rings, and ring-aggregated aromatic rings. Examples of monocyclic aromatic rings include benzene, furan, pyrrole, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, pyridine, pyrimidine, pyridazine, pyrazine, and triazine. Examples of fused aromatic rings include naphthalene, anthracene, phenalene, phenanthrene, quinoline, isoquinoline, quinazoline, phthalazine, pteridine, coumarin, indole, benzimidazole, benzofuran, and acridine. Examples of ring-aggregated aromatic rings include biphenyl, binaphthalene, bipyridine, bithiophene, phenylpyridine, phenylthiophene, terphenyl, diphenylthiophene, and quaterphenyl. Furthermore, the hydrogen atoms of the aromatic rings in the aromatic group may be substituted with, for example, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or a halogen atom. A monovalent aromatic group is an aromatic group from which one hydrogen atom has been removed, a divalent aromatic group is an aromatic group from which two hydrogen atoms have been removed, and a trivalent to hexavalent aromatic group is an aromatic group from which three to six hydrogen atoms have been removed. In this specification, "aryl group" refers to, for example, a phenyl group, naphthyl group, phenalenyl group, phenantrenyl group, anthryl group, azlenyl group, indenyl group, indanyl group, tetralinyl group, and the like. Furthermore, the hydrogen atoms of the aromatic ring in the "aryl grou