Copolymers of maleic anhydride or acid and fluorinated oleffins
AssigneeE. I. Du Pont de Nemours and Company
InventorsRobert C. Wheland, Paul D. Brothers, Colin Anolick, Charles W. Stewart SR.
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Abstract
Novel copolymers of fluorinated olefins and maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid may be made by using as solvents for the maleic anhydride or acid a perfluorinated alkyl carboxylic acid, or liquid or supercritical hexafluoropropylene or carbon dioxide. The resulting polymers are useful as adhesives or compatibilizing agents for fluoropolymers, and in coatings.
Claims34
A polymer, comprising, repeat units derived from:
- (a) at least 1 mole percent hexafluoropropylene;
- (b) at least 1 mole percent total of one or more of tetrafluoroethylene, vinyl fluoride, trifluoroethylene, ethylene, chlorotrifluoroethylene, and vinylidene fluoride;
- and
- (c) 0.03 to about 5 mole percent total of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid.
A polymer, comprising, repeat units derived from:
- (a) at least 1 mole percent tetrafluoroethylene or chlorotrifluoroethylene;
- (b) at least one mole percent of ethylene, a compound of the formula F2C═CFOR1 wherein R1 is alkyl or halogen substituted alkyl containing 1 to 10 carbon atoms and optionally containing one or more ether oxygen atoms between perfluoroalkylene or perfluoroalkyl segments, perfluoro(2-methylene-4-methyl-1,3-dioxolane), F2C═CF(CF2)pOCF═CF2 wherein p is 1 or 2, and a compound of the formula 2
- wherein R8 and R9 are each independently fluorine or perfluoroalkyl containing 1 to 4 carbon atoms;
- and
- (c) 0.03 to about 10 mole percent of one or more maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid.
A process for the production of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid copolymers with fluoroolefins by free radical polymerization in an essentially nonaqueous polymerization system, wherein the improvement comprises, using as a solvent one or more of:
- a compound of the formula R6CO2H wherein R6 is perfluoroalkyl containing 1 to 6 carbon atoms, liquid or supercritical carbon dioxide, or liquid or supercritical hexafluoropropylene.
A coated substrate in which the coating is selected from the group consisting of:
- (a) a polymer, comprising, repeat units derived from:
- (i) at least 1 mole percent hexafluoropropylene;
- (ii) at least 1 mole percent total of one or more of tetrafluoroethylene, vinyl fluoride, trifluoroethylene, chlorotrifluoroethylene, ethylene, and vinylidene fluoride;
- and
- (iii) 0.03 to about 5 mole percent total of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid;
- and
- (b) a polymer, comprising, repeat units derived from:
- (i) at least 1 mole percent tetrafluoroethylene;
- (ii) at least one mole percent of ethylene, a compound of the formula F2C═CFOR1 wherein R1 is alkyl or halogen substituted alkyl containing 1 to 10 carbon atoms and optionally containing one or more ether oxygen atoms between perfluoroalkylene or perfluoroalkyl segments, perfluoro(2-metylene-4-methyl-1,3-dioxolane), F2C═CF(CF2)pOCF═CF2 wherein p is 1 or 2, and a compound of the formula 3
- wherein R8 and R9 are each independently fluorine or perfluoroalkyl containing 1 to 4 carbon atoms;
- and
- (iii) 0.03 to about 10 mole percent of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid.
A melt blend of thermoplastic polymer and a polymer selected from the group consisting of:
- (a) a polymer, comprising, repeat units derived from:
- (i) at least 1 mole percent hexafluoropropylene;
- (ii) at least 1 mole percent total of one or more of tetrafluoroethylene, vinyl fluoride, trifluoroethylene, chlorotrifluoroethylene, ethylene, and vinylidene fluoride;
- and
- (iii) 0.03 to about 5 mole percent total of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid;
- and
- (b) a polymer, comprising, repeat units derived from:
- (i) at least 1 mole percent tetrafluoroethylene or chlorotrifluoroethylene;
- (ii) at least one mole percent of ethylene, a compound of the formula F2C═CFOR1 wherein R1 is alkyl or halogen substituted alkyl containing 1 to 10 carbon atoms and optionally containing one or more ether oxygen atoms between perfluoroalkylene or perfluoroalkyl segments, perfluoro(2-metylene-4-methyl-1,3-dioxolane), F2C═CF(CF2)pOCF═CF2 wherein p is 1 or 2, and a compound of the formula 4
- wherein R8 and R9 are each independently fluorine or perfluoroalkyl containing 1 to 4 carbon atoms;
- and
- (iii) 0.03 to about 10 mole percent of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid.
A polymer, comprising, repeat units derived from:
- (a) at least 1 mole percent vinyl fluoride, vinylidene fluoride, or chlorotrifluoroethylene;
- and
- (b) 0.03 to about 10 mole percent of one or more of maleic anhydride, maleic acid, dichloromaleic anhydride or dichloromaleic acid.
Dependencies are inferred from the claim text.