# US 2019/0315979 A1 · Curable resin composition and manufacturing method of three-dimensional object using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0315979 A1 - Document ID: US20190315979A1 - Status: Published application - Kind: A1 - Application number: 16/377,610 - Filed: 2019-04-08 - Published: 2019-10-17 - Earliest claimed: 2018-04-16 - Assignees: Canon Kabushiki Kaisha - Applicants: Canon Kabushiki Kaisha - Inventors: Takayuki Hiratani; Kyohei Wada - Web page: https://patentgrep.com/patent/US20190315979A1 ## CPC - C09D 11/102: containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds - B29C 64/291: for operating globally, e.g. together with selectively applied activators or inhibitors - B33Y 10/00: Processes of additive manufacturing - B33Y 70/00: Materials specially adapted for additive manufacturing - C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing - C09D 11/106: containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - B29K 2009/00: Use of rubber derived from conjugated dienes, as moulding material - B29K 2033/12: {Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate} - B29K 2063/00: Use of {EP, i.e.} epoxy resins {or derivatives thereof}, as moulding material - B29K 2071/00: Use of polyethers {, e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof}, as moulding material - 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) - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - B33Y: ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING - B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS ## Abstract A curable resin composition includes: an oxetane compound (A) having one oxetanyl group as a cationic polymerizable reactive group and at least one hydroxyl group; a cationic polymerizable compound (B) which is a cationic polymerizable compound other than the oxetane compound (A) and has two or more cationic polymerization reactive groups; a rubber particle (C); and a curing agent (D), wherein the oxetane compound (A) is contained at 30 parts by mass or more and 60 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B), and the rubber particle (C) has a group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) on a surface of the rubber particle (C). ## Claims ### Claim 1 A curable resin composition comprising: an oxetane compound (A) having one oxetanyl group as a cationic polymerizable reactive group and at least one hydroxyl group; a cationic polymerizable compound (B) which is a cationic polymerizable compound other than the oxetane compound (A) and has two or more cationic polymerization reactive groups; a rubber particle (C); and a curing agent (D), wherein the oxetane compound (A) is contained at 30 parts by mass or more and 60 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B), and the rubber particle (C) has a group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) on a surface of the rubber particle (C). ### Claim 2 (depends on 1) The curable resin composition according to claim 1, wherein the group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) is at least one group selected from the group consisting of a glycidyl group, an oxetanyl group, a hydroxyl group, and a carboxyl group. ### Claim 3 (depends on 2) The curable resin composition according to claim 2, wherein a resin selected from the group consisting of a (meth)acrylic acid ester-based copolymer, a copolymer of (meth)acrylic acid ester with glycidyl (meth)acrylate, and a copolymer of (meth)acrylic acid ester, glycidyl (meth)acrylate, and styrene, is provided on at least a portion of a surface of the rubber particle (C). ### Claim 4 (depends on 1) The curable resin composition according to claim 1, wherein the cationic polymerizable compound (B) has at least two or more epoxy groups as the cationic polymerization reactive group and contains 20% by mass or more and 100% by mass or less of a compound having a reactive group equivalent of 150 g/eq or more and 300 g/eq or less. ### Claim 5 (depends on 1) The curable resin composition according to claim 1, wherein the cationic polymerizable compound (B) has two or more and six or less cationic polymerization reactive groups. ### Claim 6 (depends on 1) The curable resin composition according to claim 1, wherein the rubber particle (C) is contained at 2 parts by mass or more and 70 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B). ### Claim 7 (depends on 1) The curable resin composition according to claim 1, wherein the curing agent (D) is a photocationic polymerization initiator. ### Claim 8 (depends on 7) The curable resin composition according to claim 7, wherein the photocationic polymerization initiator is contained at 0.1 parts by mass or more and 15 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B). ### Claim 9 (depends on 1) The curable resin composition according to claim 1, further comprising 0 parts by mass or more and 80 parts by mass or less of a radical polymerizable compound, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B). ### Claim 10 (depends on 9) The curable resin composition according to claim 9, wherein the radical polymerizable compound is a (meth)acrylate compound. ### Claim 11 (depends on 9) The curable resin composition according to claim 9, wherein a radical polymerization initiator is contained at 0.1 parts by mass or more and 15 parts by mass or less, based on 100 parts by mass of the radical polymerizable compound. ### Claim 12 (depends on 1) A manufacturing method of a three-dimensional object by photocuring the curable resin composition according to claim 1, based on a slice data of a three-dimensional model, the method comprising: forming a layer formed of the curable resin composition; and irradiating the layer formed of the curable resin composition with an active energy ray based on the slice data to cure the curable resin composition. ### Claim 13 (depends on 12) The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is an ultraviolet ray of a wavelength of 300 nm or more and 450 nm or less. ### Claim 14 (depends on 12) The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is concentrated in a dot shape and is used to scan, and the layer formed of the curable resin composition is irradiated with the active energy ray to cure the layer formed of the curable resin composition. ### Claim 15 (depends on 12) The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is irradiated in a planar shape through a planar plotting mask to cure the layer formed of the curable resin composition.