Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and an olefinic bond and cured articles therefrom

{
  "publication_number": "US11499032B2",
  "country": "US",
  "kind": "B2",
  "title": "Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and an olefinic bond and cured articles therefrom",
  "abstract": "Described herein are fluoropolymer compositions comprising a compound of Formula (I) wherein X 1 is selected from O or S; L is a divalent linking group comprising at least one aromatic ring; O and X 2 comprises a carbon-carbon double bond. In one embodiment, the phthalonitrile-containing compound is added to a composition comprising (i) a fluorinated elastomeric gum, wherein the fluorinated elastomeric gum comprises a fluoropolymer having a cure-site and (ii) a peroxide curing system.",
  "claims": [
    "1. A curable composition comprising (a) a fluorinated elastomeric gum comprising a fluoropolymer, wherein the fluoropolymer comprises at least one of - I, - Br, and - CN cure site, (b) a peroxide curing system comprising a peroxide and a coagent, and (c) a compound of formula I wherein X 1 is selected from O or S; L is a divalent linking group comprising at least one aromatic ring; and X 2 comprises a carbon-carbon double bond.",
    "2. The curable composition of claim 1, wherein the coagent comprises at least one of (i) diallyl ether of glycerin, (ii) triallylphosphoric acid, (iii) diallyl adipate, (iv) diallylmelamine and triallyl isocyanurate, (v) tri(methyl)allyl isocyanurate, (vi) tri(methyl)allyl cyanurate, (vii) poly-triallyl isocyanurate, (viii) xylylene-bis(diallyl isocyanurate), and (xi) CH 2 =CH-Rf1-CH═CH 2 wherein Rf1 is a perfluoroalkylene of 1 to 8 carbon atoms.",
    "3. The curable composition of claim 1, wherein the peroxide comprises at least one of 2,5-dimethyl-2,5-di(t-butylperoxy)hexane; dicumyl peroxide; di(2-t-butylperoxyisopropyl)benzene; dialkyl peroxide; bis (dialkyl peroxide); 2,5-dimethyl-2,5-di(tertiarybutylperoxy)3-hexyne; dibenzoyl peroxide; 2,4-dichlorobenzoyl peroxide; tertiarybutyl perbenzoate; α,α′-bis(t-butylperoxy-diisopropylbenzene); t-butyl peroxy isopropylcarbonate, t-butyl peroxy 2-ethylhexyl carbonate, t-amyl peroxy 2-ethylhexyl carbonate, t-hexylperoxy isopropyl carbonate, di [1,3-dimethyl-3-(t-butylperoxy)butyl] carbonate, carbonoperoxoic acid, and O,O′-1,3-propanediyl OO,OO′-bis(1,1-dimethylethyl) ester.",
    "4. The curable composition of claim 1, wherein the fluorinated elastomeric gum comprises at least one of: (i) a copolymer comprising tetrafluoroethylene, vinylidene fluoride, and hexafluoropropylene monomeric units; (ii) a copolymer comprising tetrafluoroethylene, and propylene monomeric units; (iii) a copolymer comprising tetrafluoroethylene, vinylidene fluoride, and propylene monomeric units; and (iv) a copolymer comprising vinylidene fluoride, perfluoro (methyl vinyl) ether, and hexafluoropropylene monomeric units; (v) a copolymer comprising tetrafluoroethylene, vinyl fluoride, and hexafluoropropylene monomeric units; (vi) a copolymer comprising vinyl fluoride, perfluoro (methyl vinyl) ether, and hexafluoropropylene monomeric units; (vii) a copolymer of tetrafluoroethylene with perfluorovinyl ether, and (viii) a copolymer of tetrafluoroethylene with perfluoroallyl ether.",
    "5. The curable composition of claim 1, comprising at least 0.05 parts by weight of the compound of formula I per 100 parts of the fluorinated polymer.",
    "6. The curable composition of claim 1, wherein L comprises an aromatic 6-membered ring.",
    "7. The curable composition of claim 6, wherein L is wherein R′ and R″ are independently selected from a methyl, a methoxy, an ethyl, an ethoxy, a propyl, a propoxy, a butyl, or a butoxy group.",
    "8. The curable composition of claim 6, wherein L is wherein R is selected from - S -, - O -, - C(CF 3) 2 -, - C(CH 3) 2 -, - CH 2 -, - SO 2 -, - C(═O) -, or -C(CH 3) 2 - C 6 H 4 - C(CH 3) 2 -; each R′ and each R″ are independently selected from a methyl, a methoxy, an ethyl, an ethoxy, a propyl, a propoxy, a butyl, or a butoxy group.",
    "9. The curable composition of claim 1, wherein L comprises an aromatic 5-membered ring.",
    "10. The curable composition of claim 9, wherein the aromatic 5-membered ring comprises at least one of a pyrrole, a furan, an imidazole, a pyridine, and a thiophene.",
    "11. The curable composition of claim 1, wherein X 2 comprises at least one of: - CH═CH 2, - CH 2 CH═CH 2, - OCH═CH 2, - OCH 2 CH═CH 2, - OCH 2 C(CH 3)=CH 2, - C(CH 3)=CH 2, and - OCF=CF 2.",
    "12. The curable composition of claim 1, wherein L comprises a divalent benzene.",
    "13. The curable composition of claim 1, wherein -L-X 2 is",
    "14. The curable composition of claim 1, wherein the fluorinated elastomeric gum is amorphous.",
    "15. A cured article derived from the curable composition of claim 1.",
    "16. The cured article of claim 15, wherein the article is an o-ring, a seal, a gasket, a hose, or a sheet."
  ],
  "description_excerpt": "A compound comprising a phthalonitrile group and an olefinic bond is described for use in the curing of curable fluoropolymers.\n\nThere is a desire to identify novel curing systems for fluoropolymers, which are more environmentally friendly, and have improved properties, such as improved resistance to heat aging, tensile strength, and/or elongation at break.\n\nIn one aspect, a curable composition is described comprising (a) a fluorinated elastomeric gum comprising a fluoropolymer, wherein the fluoropolymer comprises at least one of - I, - Br, and - CN cure site, (b) a peroxide curing system comprising a peroxide and a coagent, and (c) a compound of Formula I\n\nwherein X 1 is selected from O or S; L is a divalent linking group comprising at least one aromatic ring; and X 2 comprises a carbon-carbon double bond.\n\nIn another aspect, a curable composition is described comprising (a) a fluorinated elastomeric gum, wherein the fluorinated elastomeric gum comprises a fluoropolymer, and wherein the fluoropolymer comprises at least one of - I, - Br, and - CN cure site, (b) a peroxide curing system comprising a peroxide and a coagent, and (c) a compound of Formula I\n\nwherein X 1 is selected from O or S; L is a divalent linking group comprising at least one aromatic ring; and X 2 comprises a carbon-carbon double bond.\n\nIn one aspect, the curable composition from above is cured to form an article such as an o-ring, a seal, a gasket, a hose, or a sheet.\n\nThe above summary is not intended to describe each embodiment. The details of one or more embodiments of the invention are also set forth in the description below.",
  "cpc": [
    "C08K 5/372",
    "C08F 214/267",
    "C08K 5/0025",
    "C08K 5/06",
    "C08K 5/14",
    "C08K 5/29",
    "C08K 5/315",
    "C08K 5/3477",
    "C08K 5/34924",
    "F16B 43/00",
    "F16J 15/00",
    "F16J 15/102",
    "F16L 11/04"
  ],
  "ipc": [
    "C08F 214/26",
    "C08K 5/06",
    "C08K 5/14",
    "C08K 5/29",
    "C08K 5/3477",
    "C08K 5/372"
  ],
  "assignees": [
    "3M Innovative Properties Co"
  ],
  "inventors": [
    "Michael H. MITCHELL",
    "Benjamin J. Anderson",
    "Gregg D. Dahlke",
    "Tatsuo Fukushi"
  ],
  "filing_date": "2020-08-18",
  "publication_date": "2022-11-15",
  "grant_date": "2022-11-15",
  "priority_date": "2019-08-23",
  "application_number": "US-202017626215-A",
  "family_id": "72474345",
  "cited_by_count": 0,
  "citations": [
    "US5225504A",
    "US6191233B1",
    "US8138271B2",
    "US20110152487A1",
    "JP6802164B2",
    "US20180194888A1",
    "US20180155276A1",
    "US20180013553A1",
    "WO2018136331A1",
    "US20190352444A1",
    "WO2018175025A1",
    "WO2020121125A1",
    "WO2020245683A1",
    "CN112778525A"
  ]
}