# US 9,006,353 B2 · Crosslinking compounds for high glass transition temperature polymers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,006,353 B2 - Document ID: US9006353B2 - Status: Granted - Kind: B2 - Application number: 14/357,613 - Filed: 2011-11-18 - Published: 2014-10-30 - Granted: 2015-04-14 - Earliest claimed: 2011-11-18 - Assignees: Delsper LP - Applicants: William Franklin Burgoyne, Jr.; Andrew Francis Nordquist; Kerry A. Drake; Le Song - Inventors: William Franklin Burgoyne, Jr.; Andrew Francis Nordquist; Kerry A. Drake; Le Song - Web page: https://patentgrep.com/patent/US9006353B2 ## CPC - C08G 16/00: Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 (with polynitriles C08G69/38) - C08G 65/48: Polymers modified by chemical after-treatment - C08G 65/485: {Polyphenylene oxides} - C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators} - C08G 2650/20: Cross-linking - C08G 2650/40: containing ketone groups, e.g. polyarylethylketones, PEEK or PEK - 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) ## Abstract A composition having a crosslinking compound that has the following structure (I) wherein R is OH, NH2, halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000. A mixture including the composition and a polymer, a method for forming the mixture and a crosslinked polymer are also disclosed. ## Claims ### Claim 1 A composition comprising a crosslinking compound having the following structure: ### Claim 2 A mixture comprising: a composition including a crosslinking compound having the following structure: wherein R is OH, NH2, halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and a polymer containing at least one aromatic group; wherein the mixture is a substantially homogenous blend of the composition and the polymer. ### Claim 3 (depends on 2) The mixture of claim 2, wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure: (—O—Ar1—O—Ar2—)m(—O—Ar3—O—Ar4—)n where Ar1, Ar2, Ar3, and Ar4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof. ### Claim 4 (depends on 2) The mixture of claim 2, wherein the mixture is a co-precipitated blend of the composition and the polymer. ### Claim 5 (depends on 2) The mixture of claim 2, wherein the mixture is a co-evaporated blend of the composition and the polymer. ### Claim 6 (depends on 2) The mixture of claim 2, wherein the mixture is a mechanically mixed blend of the composition and the polymer. ### Claim 7 (depends on 2) The mixture of claim 2, wherein the crosslinking compound has a structure selected from a group consisting of: ### Claim 8 (depends on 2) The mixture of claim 2, wherein the crosslinking compound has the following structure: ### Claim 9 (depends on 2) The mixture of claim 2, wherein the crosslinking compound has the following structure: ### Claim 10 (depends on 2) The mixture of claim 2, wherein the crosslinking compound has the following structure: ### Claim 11 (depends on 2) The mixture of claim 2, wherein the crosslinking compound has the following structure: ### Claim 12 A method for making a polymer blend comprising: providing a composition including a crosslinking compound having the following structure: wherein R is OH, NH2, halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and providing a polymer containing at least one aromatic group; combining the composition and the polymer to form a substantially homogeneous mixture. ### Claim 13 (depends on 12) The method of claim 12, wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure: (—O—Ar1—O—Ar2—)m(—O—Ar3—O—Ar4—)n where Ar1, Ar2, Ar3, and Ar4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof. ### Claim 14 (depends on 12) The method of claim 12, wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, adding the solution to a non-solvent, and co-precipitating the composition and the polymer to form the substantially homogenous mixture. ### Claim 15 (depends on 12) The method of claim 12, wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, evaporating the solvent from the solution to form the substantially homogenous mixture. ### Claim 16 (depends on 12) The method of claim 12, wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, evaporating the solvent from the solution to form the substantially homogenous mixture. ### Claim 17 (depends on 12) The method of claim 12, wherein the combining includes mechanically blending the composition and the polymer to form the substantially homogenous mixture. ### Claim 18 (depends on 17) The method of claim 17, wherein the mechanical blending is in an extruder, ball mill, or cyrogrinder. ### Claim 19 (depends on 12) The method of claim 12, wherein the crosslinking compound has a structure selected from a group consisting of: ### Claim 20 (depends on 12) The method of claim 12, wherein the crosslinking compound has the following structure: ### Claim 21 (depends on 12) The method of claim 12, wherein the crosslinking compound has the following structure: ### Claim 22 (depends on 12) The method of claim 12, wherein the crosslinking compound has the following structure: ### Claim 23 (depends on 12) The method of claim 12, wherein the crosslinking compound has the following structure: ### Claim 24 A crosslinked polymer comprising: a reaction product of a composition including a crosslinking compound having the following structure: wherein R is OH, NH2, halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and a polymer containing at least one aromatic group. ### Claim 25 (depends on 24) The crosslinked polymer of claim 24, wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure: (—O—Ar1—O—Ar2—)m(—O—Ar3—O—Ar4—)n where Ar1, Ar2, Ar3, and Ar4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof. ### Claim 26 (depends on 24) The crosslinked polymer of claim 24, wherein the reaction product is thermally cured. ### Claim 27 (depends on 26) The crosslinked polymer of claim 26, wherein the reaction product is thermally cured by heating to temperatures greater than about 250° C. ### Claim 28 (depends on 24) The crosslinked polymer of claim 24, wherein the reaction product is radiation cured. ### Claim 29 (depends on 28) The crosslinked polymer of claim 28, wherein the reaction product is radiation cured by exposure to radiation selected from the group consisting of microwave, infrared, ultraviolet, and electron beam. ### Claim 30 (depends on 24) The crosslinked polymer of claim 24, wherein the reaction product is thermally stable at temperature greater than 260° C. ### Claim 31 (depends on 24) The crosslinked polymer of claim 24, wherein the reaction product is thermally stable at temperature greater than 400° C.