Quinone-containing polymer, methods for the manufacture thereof, and use for electrochemical gas separation
AssigneeVerdox, Inc.
InventorsCameron Rogers, Sahag Voskian
Life of this patent
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Abstract
A quinone-containing polymer includes repeating units of at least one of Formulas (I) to (IV) or a hydrogenated derivative thereof, as defined herein. Methods of manufacturing the quinone-containing polymer are also disclosed. The quinone-containing polymer can be useful in composites, electrode assemblies, electrochemical cells, gas separation systems, energy storage devices, and electrochromic devices.
Claims43
A quinone-containing polymer comprising repeating units of at least one of Formula (I) to (IV) or a hydrogenated derivative thereof
- wherein in Formulas (I) to (IV),
- X1 is —CH2— or —O—;
- X2 is —CH2— or —O—;
- X3 is —CH2— or —O—;
- X4 is —CH2— or —O—;
- R1 and R2 are independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- R3 is independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, or a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- m is 2 to 4;
- and
- the dashed lines of Formulas (II) and (IV) indicate the optional presence of one or more additional fused substituted or unsubstituted aryl groups;
- provided that when X1 is —CH2—, at least one of R1 and R2 is not hydrogen.
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A method of making a quinone-containing polymer, the method comprising:
- polymerizing a quinone-containing monomer of at least one of Formula (IX) to (XII)
- in the presence of an olefin metathesis catalyst under conditions effective to provide a quinone-containing polymer comprising repeating units of at least one of Formula (I) to (IV) or a hydrogenated derivative thereof
- wherein in in the foregoing Formulas,
- X1 is —CH2— or —O—;
- X2 is —CH2— or —O—;
- X3 is —CH2— or —O—;
- X4 is —CH2— or —O—;
- R1 and R2 are independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- R3 is independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- m is 2 to 4;
- and
- the dashed lines of Formula (II), (IV), (XI), and (XII) indicate the optional presence of one or more additional fused substituted or unsubstituted aryl groups.
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A composite comprising a quinone-containing polymer disposed on a substrate, wherein the quinone-containing polymer comprises repeating units of at least one of Formula (I) to (IV)
- wherein in Formulas (I) to (IV),
- X1 is —CH2— or —O—;
- X2 is —CH2— or —O—;
- X3 is —CH2— or —O—;
- X4 is —CH2— or —O—;
- R1 and R2 are independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- R3 is independently at each occurrence hydrogen, halogen, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-30 alkoxy group, a poly(C1-30 alkylene oxide) group, a substituted or unsubstituted C3-30 cycloalkyl group, a substituted or unsubstituted C6-30 aryl group, a substituted or unsubstituted C6-30 heteroaryl group, a nitrile group, a nitro group, a thiol group, an amine group, an amide group, an ester group, or a ketone group;
- m is 2 to 4;
- and
- the dashed lines of Formula (II) and (IV) indicate the optional presence of one or more additional fused substituted or unsubstituted aryl groups.
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A method for separating a target gas from a fluid mixture comprising the target gas, the method comprising:
- contacting the fluid mixture with a quinone-containing polymer comprising repeating units according to Formulas (I) to (IV), wherein the quinone-containing polymer is in a reduced state, to form an anion adduct between the target gas and the quinone-containing polymer in the reduced state.
Dependencies are inferred from the claim text.