# US 10,870,728 B2 · Phthalonitrile resin > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,870,728 B2 - Document ID: US10870728B2 - Status: Granted - Kind: B2 - Application number: 15/739,263 - Filed: 2016-07-01 - Published: 2018-07-12 - Granted: 2020-12-22 - Earliest claimed: 2015-07-01 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Ki Ho Ahn; Sang Woo Kim; Seung Hee Lee - Web page: https://patentgrep.com/patent/US10870728B2 ## CPC - C08G 65/333: containing nitrogen - C08G 73/0672: {with only one nitrogen atom in the ring} - C08G 75/0222: containing nitrogen - C08K 3/00: Use of inorganic substances as compounding ingredients - C08K 3/013: Fillers, pigments or reinforcing additives - C08L 71/00: Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers - C08L 81/02: Polythioethers; Polythioether-ethers - C04B 35/83: Carbon fibres in a carbon matrix - 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C04B: LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE {(roofing granules E04D7/005)}; CERAMICS (devitrified glass-ceramics C03C10/00); REFRACTORIES; TREATMENT OF NATURAL STONE ## Abstract The present application relates to a phthalonitrile resin and the like. The present application can provide a phthalonitrile resin, and a polymerizable composition and prepolymer using the same, which can exhibit excellent curability, a suitable processing temperature and a wide process window, and form a composite having excellent physical properties. Also, according to the present invention, there may be provided a phthalonitrile resin, and a polymerizable composition and prepolymer using the same, which can exhibit appropriate viscosity characteristics and thus provide a final product without deterioration of mechanical physical properties or the like due to bubbles generated during processing. ## Claims ### Claim 1 A phthalonitrile resin comprising a polymerized unit derived from a compound of Formula 1 below and an aromatic amine compound, wherein a processing temperature of a mixture comprising the compound of Formula 1 and the aromatic amine compound is 100° C. to 250° C., the processing temperature being a melting temperature or a glass transition temperature of the mixture, and wherein an absolute value of the difference between the processing temperature and a curing temperature of the mixture is 50° C. or higher: wherein in Formula 1, Ar1 and Ar2 are aromatic divalent radicals derived from an aromatic compound represented by Formula 2 below, X1 and X2 are oxygen atoms, and R1 to R10 are each independently hydrogen, an alkyl group having 1 to 4 carbon atom(s) or a cyano group, provided that at least two of R1 to R5 are each a cyano group and at least two of R6 to R10 are each a cyano group; wherein in Formula 2, one of R1 and R4 of Formula 2 forms a radical linked to the sulfur atom (S) of Formula 1, and the other of R1 and R4 of Formula 2 forms a radical linked to X1 or X2 of Formula 1, and R2, R3, R5 and R6 of Formula 2 are each independently hydrogen or an alkyl group having 1 to 4 carbon atom(s). ### Claim 2 (depends on 1) The phthalonitrile resin according to claim 1, wherein in Formula 1 R3, R4, R8 and R9 are each a cyano group, and R1, R2, R5, R6, R7 and R10 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms. ### Claim 3 A polymerizable composition comprising a compound of Formula 1 below and an aromatic amine compound, wherein a processing temperature of the polymerizable composition is 100° C. to 250° C., the processing temperature being a melting temperature or a glass transition temperature of the polymerizable composition, and wherein an absolute value of the difference between the processing temperature and a curing temperature of the polymerizable composition is 50° C. or higher: wherein, in the Formula 1, Ar1 and Ar2 of the Formula 1 are aromatic divalent radicals derived from an aromatic compound represented by Formula 2 below, X1 and X2 of the Formula 1 are oxygen atoms, and R1 to R10 of the Formula 1 are each independently hydrogen, an alkyl group having 1 to 4 carbon atom(s), or a cyano group, provided that at least two of R1 to R5 of the Formula 1 are each a cyano group and at least two of R6 to R10 of the Formula 1 are each a cyano group: Wherein, in the Formula 2, one of R1 and R4 of the Formula 2 forms a radical linked to the sulfur atom (S) of the Formula 1 and the other of R1 and R4 of the Formula 2 forms a radical linked to X1 or X2 of the Formula 1, and R2, R3, R5 and R6 of the Formula 2 are each independently hydrogen or an alkyl group having 1 to 4 carbon atom(s). ### Claim 4 (depends on 3) The polymerizable composition according to claim 3, wherein the compound of Formula 1 has a viscosity in a range of 100 cP to 10,000 cP at a temperature of 150° C. or higher. ### Claim 5 (depends on 3) A prepolymer which comprises a reacted product of the polymerizable composition of claim 3. ### Claim 6 (depends on 1) A composite comprising the phthalonitrile resin of claim 1 and a filler. ### Claim 7 (depends on 6) The composite according to claim 6, wherein the filler is a metal material, a ceramic material, glass, a metal oxide, a metal nitride or a carbon-based material.