# US 11,078,315 B2 · Copolymers of perfluorotrivinyltriazine compounds and methods for synthesizing the copolymers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,315 B2 - Document ID: US11078315B2 - Status: Granted - Kind: B2 - Application number: 16/066,535 - Filed: 2016-12-20 - Published: 2019-01-17 - Granted: 2021-08-03 - Earliest claimed: 2015-12-30 - Assignees: E. I. Du Pont de Nemours and Company - Applicants: E. I. Du Pont De Nemours and Company - Inventors: Ming-Hong Hung; Phan Linh Tang; Donald F. Lyons; Xudong Chen - Web page: https://patentgrep.com/patent/US11078315B2 ## CPC - C08F 214/262: {with fluorinated vinyl ethers} - C08F 214/222: {with fluorinated vinyl ethers} - C08F 214/282: {with fluorinated vinyl ethers} - C08F 226/06: by a heterocyclic ring containing nitrogen - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS ## Abstract Provided herein are copolymers that comprise copolymerized residues of a perfluorotrivinyltriazine monomer of Formula 1. Preferred Rf groups include, without limitation, —(CF2)n— (n=1-6); —(CF2)m—[OCF(CF3)CF2]p— (m=1-4, p=1-4); and —[(CF(CF3)—O)x—(CF2)k]— (x=1-3, k=1-5). Preferred comonomers for copolymerization with the perfluorotrivinyltriazine monomer (1) include, without limitation, tetrafluoroethylene (TFE); vinylidene fluoride (VF2); hexafluoropropylene (HFP); vinyl fluoride (VF); EVE; PSEPVE; perfluoro-(long chain vinyl ethers); E; P; PFBE; PEVE; EVE-OH; EVE-P; PDD; and the cure-site monomers BTFB, ITFB, 8-CNVE, 8-SAVE, and the like. Also provided are methods of synthesizing the copolymers and articles comprising the copolymers. ## Claims ### Claim 1 A copolymer comprising copolymerized units of a perfluorotrivinyltriazine monomer of formula (1): wherein the three Rf groups are the same or different, and wherein the three Rf groups are selected from the group consisting of —(CF2)n—, wherein 1≤n≤6; —(CF2)m—[OCF(CF3)CF2]P—, wherein 1≤m≤4 and 1≤p≤4; and —[(CF(CF3)—O)x—(CF2)k]—, wherein 1≤x≤3 and 1≤n≤6; and further comprising copolymerized units of one or more one or more cure-site monomers selected from the group consisting of bromotetrafluoro-1-butene (BTFB); iodotetrafluoro-1-butene (ITFB); and 1,1,2,2-tetrafluoro-2-((1,1,1,2,3,3-hexafluoro-3-((1,2,2-trifluorovinyl)oxy) propan-2-yl)oxy)ethane-1-sulfonyl azide (8-SAVE); said copolymer comprising no unreacted nitrile groups or a quantity of unreacted nitrile groups that is not detectable by infrared spectroscopy. ### Claim 2 (depends on 1) The copolymer of claim 1, further comprising copolymerized units of one or more comonomers selected from the group consisting of tetrafluoroethylene (TFE); vinylidene fluoride (VF2); hexafluoropropylene (HFP); vinyl fluoride (VF); 3-[1[difluoro[(trifluoroethenyl)oxy]methyl]-1,2,2,2-tetrafluoroethoxy]-2,2,3,3-tetrafluoro-, methyl ester (EVE); perfluoro-2-(2-fluorosulfonylethoxy) propyl vinyl ether (PSEPVE); perfluoro-(long chain vinyl ethers); ethylene (E); propylene (P); perfluorobutyl ethylene (PFBE); perfluoro(ethyl vinyl ether) (PEVE); 9,9-dihydro-9-hydroxyperfluoro(3,6-dioxa-5-methyl-1-nonene (EVE-OH); 1-propanol, 3-[1[difluoro[trifluoroethenyl) oxy]methyl]-1,2,2,2-tetrafluoroethoxy]-2,2,3,3-tetrafluoro-, dihydrogen phosphate (EVE-P); 1,3-dioxole, 4,5-difluoro-2,2-bis(trifluoromethyl) (PDD); perfluoro(propyl vinyl ether) (PPVE); perfluoro(methyl vinyl ether) (PMVE); and 2-(difluoromethylene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane (PMD). ### Claim 3 (depends on 2) The copolymer of claim 2, wherein the one or more comonomers are selected from the group consisting of TFE, HFP, PMVE, PPVE, and VF2. ### Claim 4 (depends on 2) The copolymer of claim 2, selected from the group consisting of dipolymers consisting of copolymerized units of the perfluorotrivinyltriazine monomer (1) with TFE or copolymerized units of the perfluorotrivinyltriazine monomer (1) with VF2; terpolymers consisting of copolymerized units of the perfluorotrivinyltriazine monomer (1) with TFE and HFP, copolymerized units of the perfluorotrivinyltriazine monomer (1) with TFE and VF2, copolymerized units of the perfluorotrivinyltriazine monomer (1) with TFE and PPVE, or copolymerized units of the perfluorotrivinyltriazine monomer (1) with TFE and PMVE; and copolymers of the perfluorotrivinyltriazine monomer (1) with TFE, VF2 and PMVE. ### Claim 5 (depends on 1) The copolymer of claim 1, comprising from about 0.5 wt % to about 25 wt % of copolymerized units of perfluorotrivinyltriazine monomer (1); and, complementarily, from about 99.5 wt % to about 75 wt % of copolymerized units of one or more comonomers, based on the total weight of the comonomer. ### Claim 6 (depends on 1) The copolymer of claim 1, comprising from about from about 1 wt % to about 10 wt % of copolymerized units of perfluorotrivinyltriazine monomer (1); and, complementarily, from about 99 to about 90 wt % of copolymerized units of one or more comonomers, based on the total weight of the comonomer. ### Claim 7 (depends on 1) The copolymer of claim 1, comprising from about 1 wt % to about 5 wt % of copolymerized units of perfluorotrivinyltriazine monomer (1); and, complementarily, from about 99 to about 95 wt % of copolymerized units of one or more comonomers, based on the total weight of the comonomer. ### Claim 8 A copolymer comprising copolymerized units of a perfluorotrivinyltriazine monomer of formula (1): wherein the three Rf groups are the same or different, and wherein the three Rf groups are selected from the group consisting of —(CF2)n—, wherein 1