Ionic liquids, functionalized particulates, and fluoropolymer composites
The present invention relates to (i) novel fluoroionic compounds capable of dispersing particulate filler compositions into a fluoropolymer; (ii) novel particulate compositions in which particulates are surface-functionalized with a fluoroionic compound; (iii) fluoropolymer composite materials containing the surface-functionalized particulates of (ii) incorporated into a fluoropolymer; (iv) crosslinked versions of (iii); v) methods for producing the crosslinked material of (iv); and (vi) articles of manufacture containing the compositions (iii) and (iv).
1. A surface-functionalized particulate composition comprising a particulate having adhered to its surface an ionic compound of the general formula
wherein:
R 3 is a hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
—R 1 —R 2 represents a vinyl group
R 4 is a fluoro-substituted hydrocarbon group having at least one carbon atom and at least one fluorine atom and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
the subscripts m and p are independently 0 or 1, where a value of 0 for a subscript represents the absence of a group to which the subscript is appended, and a value of 1 represents the presence of a group to which the subscript is appended;
X −r represents an anion with negative charge −r, where r is a value of 1, 2, or 3; and
the subscripts a and b are positive integers such that a=b×r;
wherein m is 1.
2. The particulate composition of claim 1 , wherein the particulate composition is a graphene-containing composition.
3. The particulate composition of claim 2 , wherein the particulate is selected from graphene sheets, graphite nanoparticles, carbon nanotubes, fullerenes, carbon nanohorns, carbon fibers, carbon nanofibers, carbon nanobuds, and combinations thereof.
4. The particulate composition of claim 3 , wherein p is 1.
5. The particulate composition of claim 4 , wherein R 3 is a hydrocarbon linking group having 1 to 6 carbon atoms.
6. The particulate composition of claim 5 , wherein R 4 is a fluoro-substituted hydrocarbon group having 1 to 30 carbon atoms and at least one fluorine atom.
7. The particulate composition of claim 6 , wherein all hydrogen atoms of R 4 are substituted by fluorine atoms.
8. The particulate composition of claim 7 , wherein R 4 contains 4 to 12 carbon atoms.
9. The particulate composition of claim 7 , wherein R 4 contains 6 to 10 carbon atoms.
10. A surface-functionalized particulate composition comprising a carbon-based particulate having adhered to its surface an ionic compound of the general formula
wherein:
R 3 is a hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups; —R 1 —R 2 represents a vinyl group;
R 4 is a fluoro-substituted hydrocarbon group having at least one carbon atom and at least one fluorine atom and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
the subscripts m and p are independently 0 or 1, where a value of 0 for a subscript represents the absence of a group to which the subscript is appended, and a value of 1 represents the presence of a group to which the subscript is appended;
X −r represents an anion with negative charge −r, where r is a value of 1, 2, or 3; and
the subscripts a and b are positive integers such that a=b×r.
11. A surface-functionalized particulate composition comprising a carbon-based particulate having adhered to its surface an ionic compound of the general formula
wherein:
R 3 is a hydrocarbon linking group having 1 to 6 carbon atoms;
R 4 is a fluoro-substituted hydrocarbon group having 1 to 30 carbon atoms and at least one fluorine atom;
R 5 represents a vinyl group;
X −r represents an anion with negative charge −r, where r is a value of 1, 2, or 3; and
the subscripts a and b are positive integers such that a=b×r.
12. The particulate composition of claim 11 , wherein R 4 contains 4 to 12 carbon atoms and at least one fluorine atom.
13. The particulate composition of claim 11 , wherein R 4 contains 6 to 10 carbon atoms and at least one fluorine atom.
14. An article of manufacture comprising an article constructed of a material comprising a fluoropolymer composite material comprising a fluoropolymer having incorporated therein a surface-functionalized particulate composition comprising a particulate having adhered to its surface an ionic compound of the general formula
wherein:
R 3 is a hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
—R 1 —R 2 represents a vinyl group;
R 4 is a fluoro-substituted hydrocarbon group having at least one carbon atom and at least one fluorine atom and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
the subscripts m and p are independently 0 or 1, where a value of 0 for a subscript represents the absence of a group to which the subscript is appended, and a value of 1 represents the presence of a group to which the subscript is appended;
X −r represents an anion with negative charge −r, where r is a value of 1, 2, or 3; and
the subscripts a and b are positive integers such that a=b×r.
15. The article of manufacture of claim 14 , wherein the article of manufacture is either a printing roller, tube, hose, sheet, fitted cover, protective cover, sleeve, film, block, ring, ball, part of an electrical component, or part of a medical device.
16. An article of manufacture comprising an article constructed of a material comprising a fluoropolymer composite material comprising a fluoropolymer having incorporated therein a surface-functionalized particulate composition comprising a particulate having adhered to its surface an ionic compound of the general formula
wherein:
R 3 is a hydrocarbon linking group having 1 to 6 carbon atoms;
R 4 is a fluoro-substituted hydrocarbon group having 1 to 30 carbon atoms and at least one fluorine atom;
R 5 represents a vinyl group;
X −r represents an anion with negative charge −r, where r is a value of 1, 2, or 3; and
the subscripts a and b are positive integers such that a=b×r.