Novel ionic liquids, functionalized particulates, and fluoropolymer composites
AssigneeThe Research Foundation of State University of New York
InventorsBenjamin S. Hsiao, Benjamin Chu, Jie Wei, Hongyang Ma, Feng Zuo
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Abstract
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).
Claims84
An ionic compound of the formula
- wherein:
- R1 and R3 are, independently, hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- R2 is either a hydrogen atom, or 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, or a heteroatom-containing group only when m is 1;
- R4 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.
A surface-functionalized particulate composition comprising a particulate having adhered to its surface an ionic compound of the general formula
- wherein M represents a ring or ring system containing at least one nitrogen atom in the ring or ring system;
- Ra is a hydrocarbon linking group bound to a nitrogen atom of M and having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- Rb 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 subscript v is 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;
- the subscript w is a positive integer representing the number of —(Ra)v—Rb units bound to an equal number of ring nitrogen atoms;
- +c represents a positive charge of magnitude c having a value of at least 1 and equal to the number of ring nitrogen atoms bound to —(Ra)v—Rb units;
- X−r represents an anion with negative charge −r, where r is a value of 1, 2, or 3;
- and
- the subscripts b and d are integers such that c×d=b×r.
A surface-functionalized particulate composition comprising a carbon-based particulate having adhered to its surface an ionic compound of the general formula
- wherein:
- R1 and R3 are, independently, hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- R2 is either a hydrogen atom, or 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, or a heteroatom-containing group only when m is 1;
- R4 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.
A surface-functionalized particulate composition comprising a carbon-based particulate having adhered to its surface an ionic compound of the general formula
- wherein:
- R3 is a hydrocarbon linking group having 1 to 6 carbon atoms;
- R4 is a fluoro-substituted hydrocarbon group having 1 to 30 carbon atoms and at least one fluorine atom;
- R5 is a hydrocarbon group having 1 to 6 carbon atoms;
- the subscript p is 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.
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 M represents a ring or ring system containing at least one nitrogen atom in the ring or ring system;
- Ra is a hydrocarbon linking group bound to a nitrogen atom of M and having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- Rb 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 subscript v is 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;
- the subscript w is a positive integer representing the number of —(Ra)v—Rb units bound to an equal number of ring nitrogen atoms;
- +c represents a positive charge of magnitude c having a value of at least 1 and equal to the number of ring nitrogen atoms bound to —(Ra)v—Rb units;
- X−r represents an anion with negative charge −r, where r is a value of 1, 2, or 3;
- and
- the subscripts b and d are integers such that c×d=b×r.
A fluoropolymer composite material comprising a fluoropolymer having incorporated therein a carbon-based particulate having adhered to its surface an ionic compound of the general formula
- wherein:
- R1 and R3 are, independently, hydrocarbon linking groups having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- R2 is either a hydrogen atom, or 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, or a heteroatom-containing group only when m is 1;
- R4 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.
A fluoropolymer composite material comprising a fluoropolymer having incorporated therein a carbon-based particulate having adhered to its surface an ionic compound of the general formula
- wherein:
- R3 is a hydrocarbon linking group having 1 to 6 carbon atoms;
- R4 is a fluoro-substituted hydrocarbon group having 1 to 30 carbon atoms and at least one fluorine atom;
- R5 is a hydrocarbon group having 1 to 6 carbon atoms;
- the subscript p is 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.
A method for incorporating crosslinking into a fluoropolymer composite material, the method comprising reacting crosslinkable groups residing on a fluoropolymer and/or surface of a particulate composition, both the fluoropolymer and particulate composition being in a combined state during the reacting step, wherein the crosslinking can be made to occur between fluoropolymer crosslinkable and particulate crosslinkable groups, or between fluoropolymer crosslinkable groups, or between particulate crosslinkable groups, or a combination thereof.
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 M represents a ring or ring system containing at least one nitrogen atom in the ring or ring system;
- Ra is a hydrocarbon linking group bound to a nitrogen atom of M and having at least one carbon atom, and optionally including one or more non-fluoro heteroatoms or heteroatom-containing groups;
- Rb 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 subscript v is 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;
- the subscript w is a positive integer representing the number of —(Ra)v—Rb units bound to an equal number of ring nitrogen atoms;
- +c represents a positive charge of magnitude c having a value of at least 1 and equal to the number of ring nitrogen atoms bound to —(Ra)v—Rb units;
- X−r represents an anion with negative charge −r, where r is a value of 1, 2, or 3;
- and
- the subscripts b and d are integers such that c×d=b×r.
Dependencies are inferred from the claim text.