# US 11,441,015 B2 · Coated particle > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,441,015 B2 - Document ID: US11441015B2 - Status: Granted - Kind: B2 - Application number: 16/925,436 - Filed: 2020-07-10 - Published: 2020-10-29 - Granted: 2022-09-13 - Earliest claimed: 2018-01-12 - Assignees: Ajinomoto Co., Inc. - Applicants: Ajinomoto Co., Inc. - Inventors: Eriko Sato - Web page: https://patentgrep.com/patent/US11441015B2 ## CPC - C08G 59/4021: {Ureas; Thioureas; Guanidines; Dicyandiamides} - C08K 9/10: Encapsulated ingredients - C08G 59/188: {using encapsulated compounds} - C08G 59/40: characterised by the curing agents used - C08K 3/22: of metals - C08K 5/55: Boron-containing compounds {(C08K5/0091 takes precedence)} - C09J 11/00: Features of adhesives not provided for in group C09J9/00, e.g. additives - C09J 11/06: organic - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - C08G 2170/00: Compositions for adhesives - C08K 2003/2237: {of titanium} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - 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 urea compound-containing epoxy resin curing agent particle that can impart excellent storage stability and heat stability to an epoxy resin composition including a urea compound as a curing agent, while maintaining the solubility of the urea compound during heating and the fluidity after dissolution of the urea compound. The surface of the urea compound-containing epoxy resin curing agent particle is coated with a Group 4 or Group 13 element-containing alkoxide compound, chelate compound, and/or acylate compound. ## Claims ### Claim 1 A coated particle comprising a urea compound-containing epoxy resin curing agent particle (A) and a Group 4 or Group 13 element-containing compound (B) coating a surface of the particle, wherein the Group 4 or Group 13 element-containing compound is at least one selected from the group consisting of an alkoxide compound, a chelate compound, and an acylate compound, wherein the Group 4 or Group 13 element-containing compound (B) includes (a) a compound represented by formula (1): D(OR1)n wherein in formula (1), D is a Group 4 or Group 13 element, when D is a Group 4 element, n is 4, when D is a Group 13 element, n is 3, and in each of n OR1s, R1 is independently, (i) a linear or branched saturated or unsaturated C1-20 hydrocarbon group, (ii) an acyl group represented by formula (1a): COR2, wherein in formula (1a), R2 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, or (iii) a group represented by formula (1b): R3C(O)R4, wherein in formula (1b), R3 is a linear or branched saturated or unsaturated C1-4 hydrocarbon group, and R4 is R5 or OR5, where R5 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group; and OR1 is coordinate-bonded to D through a carbonyl group in the formula (1b) to form the following cyclic structure (1c): wherein in formula (1c), the dotted line indicates a coordinate bond, (b) a compound represented by formula (2): wherein in formula (2), D, n, and R1 are the same as those defined in formula (1), and R6 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group; or (c) a 2- to 10-mer of a compound represented by the formula (1) and/or a compound represented by the formula (2). ### Claim 2 (depends on 1) The coated particle according to claim 1, wherein the Group 4 or Group 13 element in the Group 4 or Group 13 element-containing compound (B) is selected from the group consisting of boron, aluminum, titanium, and zirconium. ### Claim 3 (depends on 2) The coated particle according to claim 2, wherein the Group 4 or Group 13 element in the Group 4 or Group 13 element-containing compound (B) is boron or titanium. ### Claim 4 (depends on 1) The coated particle according to claim 1, wherein the urea compound is at least one selected from the group consisting of aromatic dimethylureas and aliphatic dimethylureas. ### Claim 5 (depends on 1) The coated particle according to claim 1, wherein the cyclic structure (1c) is represented by the following cyclic structure (1d): wherein in formula (1d), R7 is a single bond or a linear or branched saturated or unsaturated C1-3 hydrocarbon group that is optionally substituted with one or more R8s, where R8 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, V is R9 or OR9, where R9 is a hydrogen atom or a linear or branched saturated or unsaturated C1-20 hydrocarbon group, and means a single bond or a double bond, where when means a single bond, W is R9 or OR9, and when means a double bond, W is not present. ### Claim 6 (depends on 1) An epoxy resin composition comprising the coated particle according to claim 1 and an epoxy resin. ### Claim 7 (depends on 6) An adhesive comprising the epoxy resin composition according to claim 6. ### Claim 8 (depends on 1) A method for manufacturing the coated particle according to claim 1, the method comprising a step of mixing a urea compound-containing epoxy resin curing agent particle (A) and at least one selected from the group consisting of Group 4 or Group 13 element-containing alkoxide, chelate, and acylate compounds (B), wherein the Group 4 or Group 13 element-containing compound (B) includes (a) a compound represented by formula (1): D(OR1)n wherein in formula (1), D is a Group 4 or Group 13 element, when D is a Group 4 element, n is 4, when D is a Group 13 element, n is 3, and in each of n OR1s, R1 is independently, (i) a linear or branched saturated or unsaturated C1-20 hydrocarbon croup, (ii) an acyl group represented by formula (1a): COR2, wherein in formula (1a), R2 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, or (iii) a group represented by formula (1b): R3C(O)R4, wherein in formula (1b), R3 is a linear or branched saturated or unsaturated C1-4 hydrocarbon group, and R4 is R5 or OR5, where R5 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group; and OR1 is coordinate-bonded to D through a carbonyl group in the formula (1b) to form the following cyclic structure (1c): wherein in formula (1c), the dotted line indicates a coordinate bond, (b) a compound represented by formula (2): wherein in formula (2), D, n, and R1 are the same as those defined in formula (1), and R6 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group; or (c) a 2- to 10-mer of a compound represented by the formula (1) and/or a compound represented by the formula (2). ### Claim 9 A method for coating an epoxy resin curing agent particle, the method comprising a step of coating a surface of a urea compound-containing epoxy resin curing agent particle (A) with at least one selected from the group consisting of Group 4 or Group 13 element-containing alkoxide, chelate, and acylate compounds (B), wherein the Group 4 or Group 13 element-containing compound (B) includes (a) a compound represented by formula (1): D(OR1)n wherein in formula (1), D is a Group 4 or Group 13 element, when D is a Group 4 element, n is 4, when D is a Group 13 element, n is 3, and in each of n OR1s, R1 is independently, (i) a linear or branched saturated or unsaturated C1-20 hydrocarbon group, (ii) an acyl group represented by formula (1a): COR2, wherein in formula (1a), R2 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, or (iii) a group represented by formula (1b): R3C(O)R4, wherein in formula (1b), R3 is a linear or branched saturated or unsaturated C1-4 hydrocarbon group, and R4 is R5 or OR5, where R5 is a linear branched saturated or unsaturated C1-20 hydrocarbon group: and OR1 is coordinate-bonded to D through a carbonyl group in the formula (1b) to form the following cyclic structure (1c): wherein in formula (1c), the dotted line indicates a coordinate bond, (b) a compound represented by formula (2): wherein in formula (2), D, n, and R1 are the same as those defined in formula (1), and R6 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group; or (c) a 2- to 10-mer of a compound represented by the formula (1) and/or a compound represented by the formula (2). ### Claim 10 (depends on 9) The method according to claim 9, wherein the Group 4 or Group 12 element in the Group 4 or Group 13 element-containing compound (B) is selected from the group consisting f boron, aluminum, titanium, and zirconium. ### Claim 11 (depends on 10) The method according to claim 10, wherein the Group 4 or Group 13 element in the Group 4 or Group 13 element-containing compound (B) is boron or titanium. ### Claim 12 (depends on 8) The method according to claim 8, wherein the urea compound is at least one selected from the group consisting of aromatic dimethylureas and aliphatic dimethylureas. ### Claim 13 (depends on 8) The method according to claim 8, wherein the cyclic structure (1c) is represented by the following cyclic structure (1d): wherein in formula (1d), R7 is a single bond or a linear or branched saturated or unsaturated C1-3 hydrocarbon group that is optionally substituted with one or more R8s, where R8 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, V is R9 or OR9, where R9 is a hydrogen atom or a linear or branched saturated or unsaturated C1-20 hydrocarbon group, and means a single bond or a double bond, where when means a single bond, W is R9 or OR9, and when means a double bond, W is not present. ### Claim 14 (depends on 9) The method according to claim 9, wherein the Group 4 or Group 13 element in the Group 4 or Group 13 element-containing compound (B) is selected from the group consisting of boron, aluminum, titanium, and zirconium. ### Claim 15 (depends on 14) The method according to claim 14, wherein the Group 4 or Group 13 element in the Group 4 or Group 13 element-containing compound (B) is boron or titanium. ### Claim 16 (depends on 9) The method according to claim 9, wherein the urea compound is at least one selected from the group consisting of aromatic dimethylureas and aliphatic dimethylureas. ### Claim 17 (depends on 9) The method according to claim 9, wherein the cyclic structure (1c) is represented by the following cyclic structure (1d): wherein in formula (1d), R7 is a single bond or a linear or branched saturated or unsaturated C1-3 hydrocarbon group that is optionally substituted with one or more R8s, where R8 is a linear or branched saturated or unsaturated C1-20 hydrocarbon group, V is R9 or OR9, where R9 is a hydrogen atom or a linear or brandied saturated or unsaturated C1-20 hydrocarbon group, and means a single bond or a double bond, where when means a single bond, W is R9 or OR9, and when means a double bond, W is not present.