# US 2022/0153905 A1 · Polyisocyanurate Based Polymers and Fiber Reinforced Composites > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0153905 A1 - Document ID: US20220153905A1 - Status: Published application - Kind: A1 - Application number: 17/532,539 - Filed: 2021-11-22 - Published: 2022-05-19 - Earliest claimed: 2018-12-11 - Assignees: Trimer Technologies, LLC - Inventors: Henry A Sodano - Web page: https://patentgrep.com/patent/US20220153905A1 ## CPC - C08G 18/022: {the polymeric products containing isocyanurate groups} - C08G 18/003: {with epoxy compounds having no active hydrogen (with epoxy resins containing active hydrogen C08G18/58)} - C08G 18/168: {Organic compounds} - C08G 18/1816: {having carbocyclic groups} - C08G 18/1833: {having ether, acetal, or orthoester groups} - C08G 18/242: {organometallic compounds containing tin-carbon bonds} - C08G 18/794: {formed by oligomerisation of aromatic isocyanates or isothiocyanates} - C08G 59/4028: {Isocyanates; Thioisocyanates} - C08J 5/042: {with carbon fibres} - C08J 5/243: {using carbon fibres} - C08G 2115/02: to isocyanurate groups - C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) ## Abstract A method of making an isocyanurate polymer is disclosed. An isocyanate including at least one of an aromatic isocyanate and an aliphatic isocyanate is provided. A trimerization catalyst including at least one of an amine catalyst, an organometallic compound, and an imidazole compound is provided. A reaction mixture that is substantially free of reactive hydrogen is formed by mixing less than about twenty percent by total weight of said reaction mixture of an epoxide with said isocyanate. The trimerization catalyst is mixed with the reaction mixture. The reaction mixture is cured to produce a polymer composition including a reaction product of two or more isocyanates. ## Claims ### Claim 1 A method of making an isocyanurate polymer, comprising the steps of: providing an isocyanate including at least one of an aromatic isocyanate and an aliphatic isocyanate; providing a trimerization catalyst including at least one of an amine catalyst, an organometallic compound, and an imidazole compound; forming a reaction mixture being substantially free of reactive hydrogen by mixing less than about twenty percent by total weight of said reaction mixture of an epoxide with said isocyanate; mixing said trimerization catalyst with said reaction mixture; and curing said reaction mixture to produce a polymer composition including a reaction product of two or more isocyanates. ### Claim 2 (depends on 1) The method set forth in claim 1, wherein said step of providing an isocyanate is further defined by providing at least one of hexamethyl diisocyanate (HDI), methyl diphenyl diisocyanate (MDI), and polymeric methyl diphenyl diisocyanate (pMDI). ### Claim 3 (depends on 1) The method set forth in claim 1, wherein said step of providing a trimerization catalyst is further defined by providing a trimerization catalyst being substantially free of an alkylating agent. ### Claim 4 (depends on 1) The method set forth in claim 1, wherein said step of providing a trimerization catalyst is further defined by providing a trimerization catalyst being free of an alkylating agent. ### Claim 5 (depends on 1) The method set forth in claim 1, wherein said step of providing an isocyanate including at least one of an aromatic isocyanate and an aliphatic isocyanate is further defined by providing said isocyanate with a functionality of greater than 2. ### Claim 6 (depends on 1) The method set forth in claim 1, wherein said step of providing an isocyanate including at least one of an aromatic isocyanate and an aliphatic isocyanate is further defined by providing said isocyanate with a functionality of greater than 2.5. ### Claim 7 (depends on 1) The method set forth in claim 1, wherein said step of mixing less than about twenty percent by total weight of said reaction mixture of an epoxide with said isocyanate is further defined by mixing less than about ten percent by total weight of said reaction mixture of an epoxide with said isocyanate. ### Claim 8 (depends on 1) The method set forth in claim 1, wherein said step of providing an aliphatic isocyanate to said reaction mixture is further defined by providing at least one of uretidione, isocyanurate, biuret, allophanate or iminooxadiazinedione. ### Claim 9 (depends on 1) The method set forth in claim 1, further including a step of post curing said isocyanurate polymer in at least one of a humid environment, an aqueous solution. ### Claim 10 (depends on 1) The method set forth in claim 1, further including a step of post curing said isocyanurate polymer by aging said isocyanurate polymer at an ambient temperature and pressure in an environment including atmospheric moisture. ### Claim 11 (depends on 1) The method set forth in claim 1, further including a step of infusing a fibrous material with said reaction mixture after catalyzing said reaction mixture and prior to heating said reaction mixture for curing a fiber reinforced composite reaction mixture. ### Claim 12 (depends on 1) The method set forth in claim 1, wherein said step of mixing an epoxide with said reaction mixture is further defined by mixing said epoxide with said reaction mixture prior to providing said trimerization catalyst thereby forming a storage stable reaction mixture for catalyzation with said trimerization catalyst at a future time. ### Claim 13 (depends on 1) The method set forth in claim 1, wherein said step of mixing a trimerization catalyst with said reaction mixture is further defined by mixing at least one of Bis-(2-dimethylaminoethyl) ether (BDMAEE), N,N-Dimethylbenzylamine (BDMA) or 1,4-diazabicyclo [2.2.2] octane (DABCO or TEDA). ### Claim 14 (depends on 1) The method set forth in claim 1, wherein said reaction mixture includes a weight percent of 5-20% of at least one of uretdione of hexamethylene diisocyanate and a trimer of hexamethylene diisocyanate relative to a total weight of said reaction mixture. ### Claim 15 (depends on 1) The method set forth in claim 1, wherein said reaction mixture is further defined by isocyanate terminated prepolymers including at least one of urethane groups, amide groups, urea groups, uretdione groups, biuret groups, allophanate groups, isocyanurate groups or carbodiimide groups. ### Claim 16 (depends on 1) The method set forth in claim 1, wherein said step of mixing a trimerization catalyst with said reaction mixture is further defined by mixing a latent catalyst comprising a blocked amine catalyst. ### Claim 17 (depends on 1) The method set forth in claim 1, wherein said isocyanurate polymer comprises a peak heat release below 65 (kW/m2) and a maximum smoke density below 50 when tested according to Part 25 Appendix F of FAR 25.283. ### Claim 18 (depends on 1) The method set forth in claim 1, wherein said reaction mixture further includes between about 0.1 to 15 weight percent of said reaction mixture of at least one of a phosphorus ester, halogenated phosphate, halogenated compound, siloxane and metal hydroxide. ### Claim 19 A structural element formed from an isocyanurate composition, comprising: a cured isocyanurate polymeric composition formed from an isocyanate reaction mixture including an isocyanate index being greater than 300; said structural element including a peak heat release below 65 (kW/m2) and a maximum smoke density below 50 when tested according to Part 25 Appendix F of FAR 25.283. ### Claim 20 (depends on 19) The structural element set forth in claim 19, wherein the isocyanate index of the isocyanate reaction mixture is greater than 600. ### Claim 21 (depends on 19) The structural element set forth in claim 19, wherein said cured isocyanurate polymeric composition includes a weight percent of 0.1 to 15 of a total weight of said cured isocyanurate polymeric composition of at least one of a phosphorus ester, halogenated phosphate, halogenated compound, siloxane and metal hydroxide. ### Claim 22 (depends on 19) The structural element set forth in claim 19, wherein the peak heat release is below 35 (kW/m2) according to Part 25 Appendix F of FAR 25.283. ### Claim 23 (depends on 19) The structural element set forth in claim 19, wherein the maximum smoke density is below 15 when tested according to Part 25 Appendix F of FAR 25.283. ### Claim 24 (depends on 19) The structural element set forth in claim 19, wherein said isocyanurate composition includes a fibrous reinforcement comprising at least one of carbon fiber, glass fiber, alumina fiber, boron fiber, silicon carbide fiber, basalt fiber, aramid fiber, and polyethylene fiber. ### Claim 25 (depends on 19) The structural element set forth in claim 19, further comprises an electrical insulator. ### Claim 26 A method of making an isocyanurate polymer, comprising the steps of: providing an isocyanate including at least one of an aromatic isocyanate and an aliphatic isocyanate; providing a trimerization catalyst including at least one of an amine catalyst, an organometallic compound, and an imidazole compound; forming a reaction mixture being substantially free of reactive hydrogen by mixing a catalytic amount of an epoxide with said isocyanate and about 0.1 to 15 weight percent of a total weight of said reaction mixture with at least one of a phosphorus ester, halogenated phosphate, siloxane, halogenated compound and metal hydroxide; mixing said trimerization catalyst with said reaction mixture; and curing said reaction mixture to produce a polymer composition including a reaction product of two or more isocyanates. ### Claim 27 (depends on 26) The method set forth in claim 26, wherein said step of providing a trimerization catalyst is further defined by providing a trimerization catalyst being substantially free of an alkylating agent. ### Claim 28 (depends on 26) The method set forth in claim 26, wherein said isocyanurate polymer comprises a peak heat release is below 65 (kW/m2) according to Part 25 Appendix F of FAR 25.283. ### Claim 29 (depends on 26) The method set forth in claim 26, wherein said isocyanurate polymer comprises a maximum smoke density below 50 when tested according to Part 25 Appendix F of FAR 25.283. ### Claim 30 (depends on 26) The method set forth in claim 26, wherein said step of mixing a catalytic amount of an epoxide with said isocyanate is further defined by mixing less than twenty percent by total weight of said reaction mixture of epoxide with said isocyanate.