Patent
US 9,181,167CHEMICALLY-MODIFIED GRAPHENE AND METHOD FOR PRODUCING THE SAME
Mu-Yi Hua
US
Copyright © 2026 Matter42. All rights reserved.
Patent
Atlas literature
Patent
US 9,181,167Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A chemically-modified graphene comprising: a graphene layer; and a plurality of functional groups that are grafted to the graphene layer and each of which is represented by-CO--R-C OOH; wherein R is an optionally substituted C l -C₅ alkylene group or an optionally substituted Cl -C₅ alkenylene group. withdrawn
The chemically-modified graphene of claim 1, wherein R is an optionally substituted ethylene group or an optionally substituted vinylene group. withdrawn
A method for producing a chemically-modified graphene, comprising subjecting a cyclic anhydride and graphite to a Friedel-Crafts reaction in the presence of a Lewis acid, wherein the cyclic anhydride is selected from the group consisting of a maleic anhvdride- based compound, a succinic anhydride-based compound. and the combination thereof: the Lewis acid is selected from the aroun consisting of aluminum chloride. aluminum bromide, trifluoroborane, boron trichloride. borontribromide. trimethvlhoron. iron(III) chloride, magnesium bromide. and combinations thereof: and the Friedel-Craf t s reaction is conducted in a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N-methyl-2-pyrrolidone, N,N- dimethylformamide, N,N-dimethylacetamide, and combinations thereof; wherein the Friedel-Crafts reaction includes: (a) adding the Lewis acid into a cyclic anhydride solution that contains the cyclic anhydride so as to contact the cyclic anhydride with the Lewis acid to form a ring-opened intermediate at a temperature ranging from 70 * C to 120 * C; and (b) adding the graphite into the cyclic anhydride solution so as to graft the ring- opened intermediate to the graphite at a temperature ranging from 120 * C to 1 80°C. 2 PATENT S 218091-001 1
The method of claim 3, wherein the cyclic anhydride is selected from the group consisting of maleic anhydride, succinic anhydride, and the combination thereof.
The method of claim 3, wherein the molar ratio of the cyclic anhydride to the Lewis acid ranges from 1:0.5 to 1:10.
5-7. canceled
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9-11. canceled
canceled
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Embodiments described in the patent, grouped by the materials and process steps they use.
5 materials1 process step
Chemically-modified graphene (Sample 1) produced by Friedel-Crafts reaction of maleic anhydride with graphite using AlCl₃ (molar ratio maleic anhydride:AlCl₃ = 1:1) in NMP solvent. Graphite dispersed in NMP by ultrasonic vibration; maleic anhydride dissolved in NMP with AlCl₃ added and stirred at 90°C for 4 hours; graphite dispersion added dropwise at 160°C and reacted for 48 hours; product filtered through PVDF membrane, rinsed with methanol and deionized water, dried.
5 materials1 process step
Chemically-modified graphene (Sample 2) produced by same method as Example 1 except AlCl₃ amount increased to 4.08g (30 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 3) produced by same method as Example 1 except AlCl₃ amount increased to 8.16g (60 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:6.
5 materials1 process step
Chemically-modified graphene (Sample 4) produced by same method as Example 1 except maleic anhydride replaced by succinic anhydride (1g, 10 mmol); molar ratio of succinic anhydride to aluminum chloride = 1:1.
5 materials1 process step
Chemically-modified graphene (Sample 5) produced by same method as Example 4 except AlCl₃ amount increased to 4.08g; molar ratio of succinic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 6) produced by same method as Example 4 except AlCl₃ amount increased to 8.16g; molar ratio of succinic anhydride to aluminum chloride = 1:6.
Measurements and analyses referenced in the patent, with their drawing references.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
graphite (002) peak | 26.8 deg | C |
Temperature |
Patent
Atlas literature
Patent
US 9,181,167Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A chemically-modified graphene comprising: a graphene layer; and a plurality of functional groups that are grafted to the graphene layer and each of which is represented by-CO--R-C OOH; wherein R is an optionally substituted C l -C₅ alkylene group or an optionally substituted Cl -C₅ alkenylene group. withdrawn
The chemically-modified graphene of claim 1, wherein R is an optionally substituted ethylene group or an optionally substituted vinylene group. withdrawn
A method for producing a chemically-modified graphene, comprising subjecting a cyclic anhydride and graphite to a Friedel-Crafts reaction in the presence of a Lewis acid, wherein the cyclic anhydride is selected from the group consisting of a maleic anhvdride- based compound, a succinic anhydride-based compound. and the combination thereof: the Lewis acid is selected from the aroun consisting of aluminum chloride. aluminum bromide, trifluoroborane, boron trichloride. borontribromide. trimethvlhoron. iron(III) chloride, magnesium bromide. and combinations thereof: and the Friedel-Craf t s reaction is conducted in a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N-methyl-2-pyrrolidone, N,N- dimethylformamide, N,N-dimethylacetamide, and combinations thereof; wherein the Friedel-Crafts reaction includes: (a) adding the Lewis acid into a cyclic anhydride solution that contains the cyclic anhydride so as to contact the cyclic anhydride with the Lewis acid to form a ring-opened intermediate at a temperature ranging from 70 * C to 120 * C; and (b) adding the graphite into the cyclic anhydride solution so as to graft the ring- opened intermediate to the graphite at a temperature ranging from 120 * C to 1 80°C. 2 PATENT S 218091-001 1
The method of claim 3, wherein the cyclic anhydride is selected from the group consisting of maleic anhydride, succinic anhydride, and the combination thereof.
The method of claim 3, wherein the molar ratio of the cyclic anhydride to the Lewis acid ranges from 1:0.5 to 1:10.
5-7. canceled
canceled
canceled
9-11. canceled
canceled
canceled
Embodiments described in the patent, grouped by the materials and process steps they use.
5 materials1 process step
Chemically-modified graphene (Sample 1) produced by Friedel-Crafts reaction of maleic anhydride with graphite using AlCl₃ (molar ratio maleic anhydride:AlCl₃ = 1:1) in NMP solvent. Graphite dispersed in NMP by ultrasonic vibration; maleic anhydride dissolved in NMP with AlCl₃ added and stirred at 90°C for 4 hours; graphite dispersion added dropwise at 160°C and reacted for 48 hours; product filtered through PVDF membrane, rinsed with methanol and deionized water, dried.
5 materials1 process step
Chemically-modified graphene (Sample 2) produced by same method as Example 1 except AlCl₃ amount increased to 4.08g (30 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 3) produced by same method as Example 1 except AlCl₃ amount increased to 8.16g (60 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:6.
5 materials1 process step
Chemically-modified graphene (Sample 4) produced by same method as Example 1 except maleic anhydride replaced by succinic anhydride (1g, 10 mmol); molar ratio of succinic anhydride to aluminum chloride = 1:1.
5 materials1 process step
Chemically-modified graphene (Sample 5) produced by same method as Example 4 except AlCl₃ amount increased to 4.08g; molar ratio of succinic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 6) produced by same method as Example 4 except AlCl₃ amount increased to 8.16g; molar ratio of succinic anhydride to aluminum chloride = 1:6.
Measurements and analyses referenced in the patent, with their drawing references.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
graphite (002) peak | 26.8 deg | C |
Temperature |
Patent
Atlas literature
Patent
US 9,181,167Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A chemically-modified graphene comprising: a graphene layer; and a plurality of functional groups that are grafted to the graphene layer and each of which is represented by-CO--R-C OOH; wherein R is an optionally substituted C l -C₅ alkylene group or an optionally substituted Cl -C₅ alkenylene group. withdrawn
The chemically-modified graphene of claim 1, wherein R is an optionally substituted ethylene group or an optionally substituted vinylene group. withdrawn
A method for producing a chemically-modified graphene, comprising subjecting a cyclic anhydride and graphite to a Friedel-Crafts reaction in the presence of a Lewis acid, wherein the cyclic anhydride is selected from the group consisting of a maleic anhvdride- based compound, a succinic anhydride-based compound. and the combination thereof: the Lewis acid is selected from the aroun consisting of aluminum chloride. aluminum bromide, trifluoroborane, boron trichloride. borontribromide. trimethvlhoron. iron(III) chloride, magnesium bromide. and combinations thereof: and the Friedel-Craf t s reaction is conducted in a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N-methyl-2-pyrrolidone, N,N- dimethylformamide, N,N-dimethylacetamide, and combinations thereof; wherein the Friedel-Crafts reaction includes: (a) adding the Lewis acid into a cyclic anhydride solution that contains the cyclic anhydride so as to contact the cyclic anhydride with the Lewis acid to form a ring-opened intermediate at a temperature ranging from 70 * C to 120 * C; and (b) adding the graphite into the cyclic anhydride solution so as to graft the ring- opened intermediate to the graphite at a temperature ranging from 120 * C to 1 80°C. 2 PATENT S 218091-001 1
The method of claim 3, wherein the cyclic anhydride is selected from the group consisting of maleic anhydride, succinic anhydride, and the combination thereof.
The method of claim 3, wherein the molar ratio of the cyclic anhydride to the Lewis acid ranges from 1:0.5 to 1:10.
5-7. canceled
canceled
canceled
9-11. canceled
canceled
canceled
Embodiments described in the patent, grouped by the materials and process steps they use.
5 materials1 process step
Chemically-modified graphene (Sample 1) produced by Friedel-Crafts reaction of maleic anhydride with graphite using AlCl₃ (molar ratio maleic anhydride:AlCl₃ = 1:1) in NMP solvent. Graphite dispersed in NMP by ultrasonic vibration; maleic anhydride dissolved in NMP with AlCl₃ added and stirred at 90°C for 4 hours; graphite dispersion added dropwise at 160°C and reacted for 48 hours; product filtered through PVDF membrane, rinsed with methanol and deionized water, dried.
5 materials1 process step
Chemically-modified graphene (Sample 2) produced by same method as Example 1 except AlCl₃ amount increased to 4.08g (30 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 3) produced by same method as Example 1 except AlCl₃ amount increased to 8.16g (60 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:6.
5 materials1 process step
Chemically-modified graphene (Sample 4) produced by same method as Example 1 except maleic anhydride replaced by succinic anhydride (1g, 10 mmol); molar ratio of succinic anhydride to aluminum chloride = 1:1.
5 materials1 process step
Chemically-modified graphene (Sample 5) produced by same method as Example 4 except AlCl₃ amount increased to 4.08g; molar ratio of succinic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 6) produced by same method as Example 4 except AlCl₃ amount increased to 8.16g; molar ratio of succinic anhydride to aluminum chloride = 1:6.
Measurements and analyses referenced in the patent, with their drawing references.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
graphite (002) peak | 26.8 deg | C |
Temperature |
Patent
Atlas literature
Patent
US 9,181,167Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A chemically-modified graphene comprising: a graphene layer; and a plurality of functional groups that are grafted to the graphene layer and each of which is represented by-CO--R-C OOH; wherein R is an optionally substituted C l -C₅ alkylene group or an optionally substituted Cl -C₅ alkenylene group. withdrawn
The chemically-modified graphene of claim 1, wherein R is an optionally substituted ethylene group or an optionally substituted vinylene group. withdrawn
A method for producing a chemically-modified graphene, comprising subjecting a cyclic anhydride and graphite to a Friedel-Crafts reaction in the presence of a Lewis acid, wherein the cyclic anhydride is selected from the group consisting of a maleic anhvdride- based compound, a succinic anhydride-based compound. and the combination thereof: the Lewis acid is selected from the aroun consisting of aluminum chloride. aluminum bromide, trifluoroborane, boron trichloride. borontribromide. trimethvlhoron. iron(III) chloride, magnesium bromide. and combinations thereof: and the Friedel-Craf t s reaction is conducted in a polar aprotic solvent selected from the group consisting of dimethyl sulfoxide, N-methyl-2-pyrrolidone, N,N- dimethylformamide, N,N-dimethylacetamide, and combinations thereof; wherein the Friedel-Crafts reaction includes: (a) adding the Lewis acid into a cyclic anhydride solution that contains the cyclic anhydride so as to contact the cyclic anhydride with the Lewis acid to form a ring-opened intermediate at a temperature ranging from 70 * C to 120 * C; and (b) adding the graphite into the cyclic anhydride solution so as to graft the ring- opened intermediate to the graphite at a temperature ranging from 120 * C to 1 80°C. 2 PATENT S 218091-001 1
The method of claim 3, wherein the cyclic anhydride is selected from the group consisting of maleic anhydride, succinic anhydride, and the combination thereof.
The method of claim 3, wherein the molar ratio of the cyclic anhydride to the Lewis acid ranges from 1:0.5 to 1:10.
5-7. canceled
canceled
canceled
9-11. canceled
canceled
canceled
Embodiments described in the patent, grouped by the materials and process steps they use.
5 materials1 process step
Chemically-modified graphene (Sample 1) produced by Friedel-Crafts reaction of maleic anhydride with graphite using AlCl₃ (molar ratio maleic anhydride:AlCl₃ = 1:1) in NMP solvent. Graphite dispersed in NMP by ultrasonic vibration; maleic anhydride dissolved in NMP with AlCl₃ added and stirred at 90°C for 4 hours; graphite dispersion added dropwise at 160°C and reacted for 48 hours; product filtered through PVDF membrane, rinsed with methanol and deionized water, dried.
5 materials1 process step
Chemically-modified graphene (Sample 2) produced by same method as Example 1 except AlCl₃ amount increased to 4.08g (30 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 3) produced by same method as Example 1 except AlCl₃ amount increased to 8.16g (60 mmol); molar ratio of maleic anhydride to aluminum chloride = 1:6.
5 materials1 process step
Chemically-modified graphene (Sample 4) produced by same method as Example 1 except maleic anhydride replaced by succinic anhydride (1g, 10 mmol); molar ratio of succinic anhydride to aluminum chloride = 1:1.
5 materials1 process step
Chemically-modified graphene (Sample 5) produced by same method as Example 4 except AlCl₃ amount increased to 4.08g; molar ratio of succinic anhydride to aluminum chloride = 1:3.
5 materials1 process step
Chemically-modified graphene (Sample 6) produced by same method as Example 4 except AlCl₃ amount increased to 8.16g; molar ratio of succinic anhydride to aluminum chloride = 1:6.
Measurements and analyses referenced in the patent, with their drawing references.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
graphite (002) peak | 26.8 deg | C |
Temperature |
| 80–100 °C |
| — |
Temperature | 120–180 °C | — |
| 80–100 °C |
| — |
Temperature | 120–180 °C | — |
| 80–100 °C |
| — |
Temperature | 120–180 °C | — |
| 80–100 °C |
| — |
Temperature | 120–180 °C | — |