# US 12,110,356 B2 · Heat-curable resin composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,110,356 B2 - Document ID: US12110356B2 - Status: Granted - Kind: B2 - Application number: 17/869,197 - Filed: 2022-07-20 - Published: 2023-03-02 - Granted: 2024-10-08 - Earliest claimed: 2021-08-02 - Assignees: Shin-Etsu Chemical Co., Ltd. - Applicants: Shin-Etsu Chemical Co., Ltd. - Inventors: Naoyuki Kushihara; Rina Sasahara - Web page: https://patentgrep.com/patent/US12110356B2 ## CPC - C08F 283/10: on to polymers containing more than one epoxy radical per molecule {(C08F283/004 takes precedence)} - C09D 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - C09J 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) ## Abstract Provided is a heat-curable resin composition capable of being turned into a cured product having a low relative permittivity, a low dielectric tangent, an excellent adhesiveness and a high resistance. The heat-curable resin composition contains: (A) a citraconimide compound; (B) an epoxy resin; (C) an epoxy resin curing agent; and (D) a curing accelerator. ## Claims ### Claim 1 A heat-curable resin composition comprising: one or more of each of (A) a citraconimide compound; (B) an epoxy resin; (C) an epoxy resin curing agent; and (D) a curing accelerator, wherein the epoxy resin curing agent (C) is at least one selected from an amine compound, a phenolic compound, an acid anhydride compound and an active ester compound. ### Claim 2 (depends on 1) The heat-curable resin composition according to claim 1, wherein the citraconimide compound (A) is a biscitraconimide compound represented by the following formula (1): wherein A represents a divalent organic group. ### Claim 3 (depends on 2) The heat-curable resin composition according to claim 2, wherein A in the formula (1) is selected from the groups of the following structures and dimer acid skeleton-derived hydrocarbon groups: wherein * represents a bond to a nitrogen atom in the citraconimide group; n is 1 to 20. ### Claim 4 (depends on 1) The heat-curable resin composition according to claim 1, wherein the curing accelerator (D) contains at least one of an imidazole-based curing accelerator, an organic phosphorus-based curing accelerator and a tertiary amine-based curing accelerator. ### Claim 5 (depends on 1) The heat-curable resin composition according to claim 1, wherein the epoxy resin (B) has at least two epoxy groups per each molecule. ### Claim 6 (depends on 1) The heat-curable resin composition according to claim 1, wherein the component (B) is contained in an amount of 1 to 900 parts by mass per 100 parts by mass of the component (A), a molar equivalent ratio of functional groups in the curing agent as the component (C) that are reactive with epoxy groups to 1 molar equivalent of epoxy groups in the epoxy resin (B) is 0.1 to 4.0, and the component (D) is contained in an amount of 0.01 to 20 parts by mass per 100 parts by mass of the component (A). ### Claim 7 (depends on 1) The heat-curable resin composition according to claim 1, wherein the citraconimide compound (A) has a number average molecular weight of 200 to 10,000. ### Claim 8 (depends on 1) An adhesive agent comprising the heat-curable resin composition according to claim 1. ### Claim 9 (depends on 1) A semiconductor encapsulation material comprising the heat-curable resin composition according to claim 1. ### Claim 10 A heat-curable resin composition consisting essentially of: one or more of each of (A) a citraconimide compound; (B) an epoxy resin; (C) an epoxy resin curing agent; (D) a curing accelerator; and optionally, one or more of an inorganic filler, a flame retardant, an ion trapping agent, an antioxidant, an adhesiveness imparting agent, a low stress agent and a colorant, wherein the epoxy resin curing agent (C) is at least one selected from an amine compound, a phenolic compound, an acid anhydride compound and an active ester compound. ### Claim 11 (depends on 1) The heat-curable resin composition according to claim 1, which consists of one or more of each of said components (A), (B), (C) and (D) and optionally one or more of an inorganic filler, a flame retardant, an ion trapping agent, an antioxidant, an adhesiveness imparting agent, a low stress agent and a colorant. ### Claim 12 (depends on 11) The heat-curable resin composition according to claim 11, which consists of one or more of each of said components (A), (B), (C) and (D). ### Claim 13 (depends on 1) The heat-curable resin composition according to claim 1, which comprises one or more of each of (A); (B) in an amount of 3 to 200 parts by mass, per 100 parts by mass of the component (A), (C) in an amount at which a molar equivalent ratio of the functional groups in the epoxy resin curing agent to 1 molar equivalent of the epoxy groups in the component (B) is 0.2 to 2.0; particularly preferably 0.4 to 1.0; and (D) in an amount of preferably 0.5 to 10 parts by mass, per 100 parts by mass of the component (A). ### Claim 14 (depends on 11) The heat-curable resin composition according to claim 11, which consists of one or more of each of (A); (B) in an amount of 3 to 200 parts by mass, per 100 parts by mass of the component (A); (C) in an amount at which a molar equivalent ratio of the functional groups in the epoxy resin curing agent to 1 molar equivalent of the epoxy groups in the component (B) is 0.2 to 2.0, particularly preferably 0.4 to 1.0; and (D) in an amount of preferably 0.5 to 10 parts by mass, per 100 parts by mass of the component (A); and optionally, one or more of said optional components. ### Claim 15 (depends on 11) The heat-curable resin composition according to claim 11, which consists of one or more of each of (A); (B) in an amount of 3 to 200 parts by mass, per 100 parts by mass of the component (A); (C) in an amount at which a molar equivalent ratio of the functional groups in the epoxy resin curing agent to 1 molar equivalent of the epoxy groups in the component (B) is 0.2 to 2.0, particularly preferably 0.4 to 1.0; and (D) in an amount of preferably 0.5 to 10 parts by mass, per 100 parts by mass of the component (A).