Patent
US 9,318,231METHOD OF PREPARING REDUCED GRAPHENE OXIDE AND REDUCED GRAPHENE OXIDE-POLYMER COMPOSITES
Bon-Cheol KU
US
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US 9,318,231Patent drawings and their descriptions. Click a drawing to enlarge it.
FIGS. 1 A through 1 C are schematic diagrams illustrating a structure in which a halogen- substituted aromatic compound is covalently bound to a graphene oxide …
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(curren tl y amended) A method of prepa ri ng a reduced graphene o xi de RGO), the method comprising: mixi ng a graphene oxid e and a ha lo gen-subs tit uted aro mat ic compounds compound; stirring the mixture to obtain a graphene oxide [[with]] covalently bound to the halogen-subs ti tuted aroma tic compounds cova; ently bundthereto c ompound and heat treat i ng the graphene oxide [[with]] covalently bound to the ha logen- substi t uted aromat ic componds-covalently-bound-t heret o- comp ou nd at a temperature in a range of 100 to 45 0 C to prepare the RGO.
(curren t ly amended) The method of claim 1, wher ei n the halogen-substituted aromatic compounds-are- is a compound r epre sented by Formula 1 below: R-- Ar-L < Formu la 1> wher ei n R i s H or a ha lo gen atom, Ar i s a subs ti tuted or unsubst i tuted C 6LC₁ 4 aro matic ring, L i s -OH, -COOH, -NH2,-N₂TX-, or -NH- --- NH2, where X-is a monova l ent Page 2 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 counter anion, provided that w h e n R i s H, A r i s subst i tuted with at l east one halogen atom.
8. (curren t ly amended) The method of claim 1, wher ein [[a]] the co valent bond between that covalentl binds the graphene oxide to the ha l oge n- substituted aromatic compoundsand-the-gaphene-e x id compound i s formed on a plane or an edge of the graphene oxide.
(Orig inal) A reduced graphene o xi de prepared using the method of claim 1 and having an el ect rical conduc t ivity in a rang e of 10 to 1 00, 000 S/m. Page 6 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(Or iginal) The method of c l aim 1, wher ei n the graphene oxid e i s pr e pared by treating graphite w it h a strong acid.
(Orig ina l) The method o f cl aim 3, wherein in Formu l a 1 Ar is a pheny l ene group, a naphthy le ne group, or an anthracen yl ene group.
(current l y amended) The method of cl aim 3, wherein the ha logen- substituted SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.11.522.1427.1873.1996.svg 1.897 4.503 Chemistry Black and white aromatic compound s com p ou nd of Formul a 1 is se le cte d f rom the roup consistin one-of the-compounds-below-
SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.15.300.2164.634.2344.svg 0.60 1.113 Chemistry Black and white SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.17.300.2403.901.2645.svg 0.807 2.003 Chemistry Black and white 7. The method of clai m 1, wherein an amount of the halogen-substituted aromatic compounds compound is i n a range of 1 to 30 parts by w ei ght based on 100 parts by weight of the graphene oxide. Page 3 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(curren tl y amended) The method of c lai m 1, wher e in the ha lo gen-substituted aro matic compo und s- are compound is a ha logen- substi t uted aromatic hydra z ine.
(Original) The method of claim 9, where in the ha l oge n- subs ti tuted aromatic hydraz i ne form s a compound having an indol e structur e by [3,3]-sigmatrop ic rearrangement with the graphene o xi de.
1 0. (Orig inal) The method of cl aim 9, wher ei n the halogen-substituted aroma tic hydrazine is ha l oge n- substitu t ed phen yl hydraz i ne or ha loge n-substituted naphthy l hydrazine.
(curren tl y amended) The method of cl aim 1, wherein the graphene oxide [[with]] covalently bound to the ha log en-substituted aroma ti c compound covalently-baund thereto i s heat treated at a temperature ranging from 100 to 450 C [[.]], for 1 to 10 hours in a ir or in a nitrogen atmosphere.
A method of prepa ring a reduced graphene o xide-poly mer composites, the method comprising: Page 4 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 mixi ng a graphene oxide and a ha logen- subs ti tuted aro matic compounds; stirring the m ixtur e to obta in a graphene oxide wi th th e ha l oge n- substituted aromatic compounds cova lent ly bound thereto; mixi ng the graphene oxide with the halogen-subst it uted aroma tic compounds c ovalently bound thereto and a heat-resistant po lym er precursors and drying the m ix ture to obtain a graphene oxide -polym er precursor composites; and heat treating the graphene o xi de-po l ymer precursor composites at a te m perature in a range of 100 to 45 0 C. withdrawn
(Withdrawn) The method of cl aim 13, wherein the heat -resi stant polymer precursor compris e s any one of po lyami c a ci d (PAA), po l yacry l onitr il e (PAN), hydroxy l- containing polyam ic a ci d (PAA), and hydroxy l- contain i ng po l yam i de. withdrawn
1 5. (Withdrawn) The m ethod of clai m 13, wherein an a m ount o f the graphene oxide w ith the ha l ogen-subs ti tuted aro mati c compounds covalen tl y bound thereto is i n a range of 1 to 40 parts by weight based on 100 parts by weight of the heat -resi stant po l ymer precursors. withdrawn
(Withdrawn) A method of prepa ri ng reduced graphene oxide-polymer co m pos i tes, the method comprising: m ixing a graphene oxide and a ha l oge n- subs ti tuted aromatic compounds; stirring the m i xture to obtain a graphene o xi de with the halogen-substituted aromatic compounds cova lent ly bound thereto: mixi ng the graphene oxide with the ha l ogen-subs ti tuted aro mati c compounds cov al ent ly bound ther e to and monomers fo r p ol ymerization; and heat treat in g the mixture at a temperature i n a range of 100 to 45 0 C. withdrawn
The method of claim 16, wherein in the reduced graphe n e ox ide- polymer compos it es the po lym ers comp ri se any one of po lyol efin, po l yester, po lyamide, poly benzimidazo l e (P BI), and po ly benzoxazo l e (P B O). withdrawn
1 7. (Withdrawn) The m ethod of clai m 16, wherein an a m ount o f the h al oge n- subst i tuted aromatic compound i s in a range of 1 to 40 parts by weight based on 100 parts by weight of the monomers. Page 5 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 withdrawn
(W ithdrawn) The method of cl aim 16, wherein at l east one of a po l ymer ization catalyst, a po l yme ri zation initiator, a th e rma l sta bil izer, and an antioxidant i s further added to the mixture of the graphene o xi de with the ha l ogen-subst itu ted aromatic compounds cova lentl y bound thereto and monomers for po ly meriza ti on. withdrawn
1 9. The method of clai m 13, wherein i n the reduced graphene oxide-polymer composites the po lyme rs comprise any one o f po lyol efin, po l yester, po lyami de, pol yben zimi dazo l e (P SI), and po l ybenzoxazo l e (P BO). withdrawn
The method of c l aim 13, wherein the graphene oxide is prepar e d by trea ti ng graphite with a strong acid. withdrawn
(Withdrawn) The method of clai m 16, wherein the graphene o xi de i s prepared by trea ti ng graph i te w it h a strong acid. withdrawn
The method of cl aim 13, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds is in a range of 1 to 30 parts by weight based on 100 parts by weight of the graphe n e oxide. withdrawn
The method of clai m 16, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds i s in a range of 1 to 30 parts by w ei ght based on 100 parts by weig ht of the graphene oxide. withdrawn
(Wt hdrawn) A reduced graphene ox ide-polym er co m pos it es prepared us ing the method o f clai m 13 and having an e lect rica l conductivity i n a range of 0.01 to 1,000 S/rm
(Withdrawn) A reduced graphene ox i de-po l ymer composites prepared us ing the method of clai m 16 and having an e l ect rical conduct ivi ty i n a range of 0.01 to 1,000 S/rn. Page 7 of 9 withdrawn
Materials described outside the worked examples.
graphene oxide
halogen-substituted aromatic compound
Additional fabrication and treatment steps described in the patent.
Measurements and analyses referenced in the patent, with their drawing references.
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Electrical Conductivity | 10–100000 S/m | reduced graphene oxide |
Electrical Conductivity | 0.01–1000 S/m |
Related documents with shared materials, methods, properties, or citations.
Patent
Atlas literature
Patent
US 9,318,231Patent drawings and their descriptions. Click a drawing to enlarge it.
FIGS. 1 A through 1 C are schematic diagrams illustrating a structure in which a halogen- substituted aromatic compound is covalently bound to a graphene oxide …
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(curren tl y amended) A method of prepa ri ng a reduced graphene o xi de RGO), the method comprising: mixi ng a graphene oxid e and a ha lo gen-subs tit uted aro mat ic compounds compound; stirring the mixture to obtain a graphene oxide [[with]] covalently bound to the halogen-subs ti tuted aroma tic compounds cova; ently bundthereto c ompound and heat treat i ng the graphene oxide [[with]] covalently bound to the ha logen- substi t uted aromat ic componds-covalently-bound-t heret o- comp ou nd at a temperature in a range of 100 to 45 0 C to prepare the RGO.
(curren t ly amended) The method of claim 1, wher ei n the halogen-substituted aromatic compounds-are- is a compound r epre sented by Formula 1 below: R-- Ar-L < Formu la 1> wher ei n R i s H or a ha lo gen atom, Ar i s a subs ti tuted or unsubst i tuted C 6LC₁ 4 aro matic ring, L i s -OH, -COOH, -NH2,-N₂TX-, or -NH- --- NH2, where X-is a monova l ent Page 2 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 counter anion, provided that w h e n R i s H, A r i s subst i tuted with at l east one halogen atom.
8. (curren t ly amended) The method of claim 1, wher ein [[a]] the co valent bond between that covalentl binds the graphene oxide to the ha l oge n- substituted aromatic compoundsand-the-gaphene-e x id compound i s formed on a plane or an edge of the graphene oxide.
(Orig inal) A reduced graphene o xi de prepared using the method of claim 1 and having an el ect rical conduc t ivity in a rang e of 10 to 1 00, 000 S/m. Page 6 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(Or iginal) The method of c l aim 1, wher ei n the graphene oxid e i s pr e pared by treating graphite w it h a strong acid.
(Orig ina l) The method o f cl aim 3, wherein in Formu l a 1 Ar is a pheny l ene group, a naphthy le ne group, or an anthracen yl ene group.
(current l y amended) The method of cl aim 3, wherein the ha logen- substituted SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.11.522.1427.1873.1996.svg 1.897 4.503 Chemistry Black and white aromatic compound s com p ou nd of Formul a 1 is se le cte d f rom the roup consistin one-of the-compounds-below-
SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.15.300.2164.634.2344.svg 0.60 1.113 Chemistry Black and white SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.17.300.2403.901.2645.svg 0.807 2.003 Chemistry Black and white 7. The method of clai m 1, wherein an amount of the halogen-substituted aromatic compounds compound is i n a range of 1 to 30 parts by w ei ght based on 100 parts by weight of the graphene oxide. Page 3 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(curren tl y amended) The method of c lai m 1, wher e in the ha lo gen-substituted aro matic compo und s- are compound is a ha logen- substi t uted aromatic hydra z ine.
(Original) The method of claim 9, where in the ha l oge n- subs ti tuted aromatic hydraz i ne form s a compound having an indol e structur e by [3,3]-sigmatrop ic rearrangement with the graphene o xi de.
1 0. (Orig inal) The method of cl aim 9, wher ei n the halogen-substituted aroma tic hydrazine is ha l oge n- substitu t ed phen yl hydraz i ne or ha loge n-substituted naphthy l hydrazine.
(curren tl y amended) The method of cl aim 1, wherein the graphene oxide [[with]] covalently bound to the ha log en-substituted aroma ti c compound covalently-baund thereto i s heat treated at a temperature ranging from 100 to 450 C [[.]], for 1 to 10 hours in a ir or in a nitrogen atmosphere.
A method of prepa ring a reduced graphene o xide-poly mer composites, the method comprising: Page 4 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 mixi ng a graphene oxide and a ha logen- subs ti tuted aro matic compounds; stirring the m ixtur e to obta in a graphene oxide wi th th e ha l oge n- substituted aromatic compounds cova lent ly bound thereto; mixi ng the graphene oxide with the halogen-subst it uted aroma tic compounds c ovalently bound thereto and a heat-resistant po lym er precursors and drying the m ix ture to obtain a graphene oxide -polym er precursor composites; and heat treating the graphene o xi de-po l ymer precursor composites at a te m perature in a range of 100 to 45 0 C. withdrawn
(Withdrawn) The method of cl aim 13, wherein the heat -resi stant polymer precursor compris e s any one of po lyami c a ci d (PAA), po l yacry l onitr il e (PAN), hydroxy l- containing polyam ic a ci d (PAA), and hydroxy l- contain i ng po l yam i de. withdrawn
1 5. (Withdrawn) The m ethod of clai m 13, wherein an a m ount o f the graphene oxide w ith the ha l ogen-subs ti tuted aro mati c compounds covalen tl y bound thereto is i n a range of 1 to 40 parts by weight based on 100 parts by weight of the heat -resi stant po l ymer precursors. withdrawn
(Withdrawn) A method of prepa ri ng reduced graphene oxide-polymer co m pos i tes, the method comprising: m ixing a graphene oxide and a ha l oge n- subs ti tuted aromatic compounds; stirring the m i xture to obtain a graphene o xi de with the halogen-substituted aromatic compounds cova lent ly bound thereto: mixi ng the graphene oxide with the ha l ogen-subs ti tuted aro mati c compounds cov al ent ly bound ther e to and monomers fo r p ol ymerization; and heat treat in g the mixture at a temperature i n a range of 100 to 45 0 C. withdrawn
The method of claim 16, wherein in the reduced graphe n e ox ide- polymer compos it es the po lym ers comp ri se any one of po lyol efin, po l yester, po lyamide, poly benzimidazo l e (P BI), and po ly benzoxazo l e (P B O). withdrawn
1 7. (Withdrawn) The m ethod of clai m 16, wherein an a m ount o f the h al oge n- subst i tuted aromatic compound i s in a range of 1 to 40 parts by weight based on 100 parts by weight of the monomers. Page 5 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 withdrawn
(W ithdrawn) The method of cl aim 16, wherein at l east one of a po l ymer ization catalyst, a po l yme ri zation initiator, a th e rma l sta bil izer, and an antioxidant i s further added to the mixture of the graphene o xi de with the ha l ogen-subst itu ted aromatic compounds cova lentl y bound thereto and monomers for po ly meriza ti on. withdrawn
1 9. The method of clai m 13, wherein i n the reduced graphene oxide-polymer composites the po lyme rs comprise any one o f po lyol efin, po l yester, po lyami de, pol yben zimi dazo l e (P SI), and po l ybenzoxazo l e (P BO). withdrawn
The method of c l aim 13, wherein the graphene oxide is prepar e d by trea ti ng graphite with a strong acid. withdrawn
(Withdrawn) The method of clai m 16, wherein the graphene o xi de i s prepared by trea ti ng graph i te w it h a strong acid. withdrawn
The method of cl aim 13, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds is in a range of 1 to 30 parts by weight based on 100 parts by weight of the graphe n e oxide. withdrawn
The method of clai m 16, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds i s in a range of 1 to 30 parts by w ei ght based on 100 parts by weig ht of the graphene oxide. withdrawn
(Wt hdrawn) A reduced graphene ox ide-polym er co m pos it es prepared us ing the method o f clai m 13 and having an e lect rica l conductivity i n a range of 0.01 to 1,000 S/rm
(Withdrawn) A reduced graphene ox i de-po l ymer composites prepared us ing the method of clai m 16 and having an e l ect rical conduct ivi ty i n a range of 0.01 to 1,000 S/rn. Page 7 of 9 withdrawn
Materials described outside the worked examples.
graphene oxide
halogen-substituted aromatic compound
Additional fabrication and treatment steps described in the patent.
Measurements and analyses referenced in the patent, with their drawing references.
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Electrical Conductivity | 10–100000 S/m | reduced graphene oxide |
Electrical Conductivity | 0.01–1000 S/m |
Related documents with shared materials, methods, properties, or citations.
Patent
Atlas literature
Patent
US 9,318,231Patent drawings and their descriptions. Click a drawing to enlarge it.
FIGS. 1 A through 1 C are schematic diagrams illustrating a structure in which a halogen- substituted aromatic compound is covalently bound to a graphene oxide …
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(curren tl y amended) A method of prepa ri ng a reduced graphene o xi de RGO), the method comprising: mixi ng a graphene oxid e and a ha lo gen-subs tit uted aro mat ic compounds compound; stirring the mixture to obtain a graphene oxide [[with]] covalently bound to the halogen-subs ti tuted aroma tic compounds cova; ently bundthereto c ompound and heat treat i ng the graphene oxide [[with]] covalently bound to the ha logen- substi t uted aromat ic componds-covalently-bound-t heret o- comp ou nd at a temperature in a range of 100 to 45 0 C to prepare the RGO.
(curren t ly amended) The method of claim 1, wher ei n the halogen-substituted aromatic compounds-are- is a compound r epre sented by Formula 1 below: R-- Ar-L < Formu la 1> wher ei n R i s H or a ha lo gen atom, Ar i s a subs ti tuted or unsubst i tuted C 6LC₁ 4 aro matic ring, L i s -OH, -COOH, -NH2,-N₂TX-, or -NH- --- NH2, where X-is a monova l ent Page 2 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 counter anion, provided that w h e n R i s H, A r i s subst i tuted with at l east one halogen atom.
8. (curren t ly amended) The method of claim 1, wher ein [[a]] the co valent bond between that covalentl binds the graphene oxide to the ha l oge n- substituted aromatic compoundsand-the-gaphene-e x id compound i s formed on a plane or an edge of the graphene oxide.
(Orig inal) A reduced graphene o xi de prepared using the method of claim 1 and having an el ect rical conduc t ivity in a rang e of 10 to 1 00, 000 S/m. Page 6 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(Or iginal) The method of c l aim 1, wher ei n the graphene oxid e i s pr e pared by treating graphite w it h a strong acid.
(Orig ina l) The method o f cl aim 3, wherein in Formu l a 1 Ar is a pheny l ene group, a naphthy le ne group, or an anthracen yl ene group.
(current l y amended) The method of cl aim 3, wherein the ha logen- substituted SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.11.522.1427.1873.1996.svg 1.897 4.503 Chemistry Black and white aromatic compound s com p ou nd of Formul a 1 is se le cte d f rom the roup consistin one-of the-compounds-below-
SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.15.300.2164.634.2344.svg 0.60 1.113 Chemistry Black and white SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.17.300.2403.901.2645.svg 0.807 2.003 Chemistry Black and white 7. The method of clai m 1, wherein an amount of the halogen-substituted aromatic compounds compound is i n a range of 1 to 30 parts by w ei ght based on 100 parts by weight of the graphene oxide. Page 3 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(curren tl y amended) The method of c lai m 1, wher e in the ha lo gen-substituted aro matic compo und s- are compound is a ha logen- substi t uted aromatic hydra z ine.
(Original) The method of claim 9, where in the ha l oge n- subs ti tuted aromatic hydraz i ne form s a compound having an indol e structur e by [3,3]-sigmatrop ic rearrangement with the graphene o xi de.
1 0. (Orig inal) The method of cl aim 9, wher ei n the halogen-substituted aroma tic hydrazine is ha l oge n- substitu t ed phen yl hydraz i ne or ha loge n-substituted naphthy l hydrazine.
(curren tl y amended) The method of cl aim 1, wherein the graphene oxide [[with]] covalently bound to the ha log en-substituted aroma ti c compound covalently-baund thereto i s heat treated at a temperature ranging from 100 to 450 C [[.]], for 1 to 10 hours in a ir or in a nitrogen atmosphere.
A method of prepa ring a reduced graphene o xide-poly mer composites, the method comprising: Page 4 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 mixi ng a graphene oxide and a ha logen- subs ti tuted aro matic compounds; stirring the m ixtur e to obta in a graphene oxide wi th th e ha l oge n- substituted aromatic compounds cova lent ly bound thereto; mixi ng the graphene oxide with the halogen-subst it uted aroma tic compounds c ovalently bound thereto and a heat-resistant po lym er precursors and drying the m ix ture to obtain a graphene oxide -polym er precursor composites; and heat treating the graphene o xi de-po l ymer precursor composites at a te m perature in a range of 100 to 45 0 C. withdrawn
(Withdrawn) The method of cl aim 13, wherein the heat -resi stant polymer precursor compris e s any one of po lyami c a ci d (PAA), po l yacry l onitr il e (PAN), hydroxy l- containing polyam ic a ci d (PAA), and hydroxy l- contain i ng po l yam i de. withdrawn
1 5. (Withdrawn) The m ethod of clai m 13, wherein an a m ount o f the graphene oxide w ith the ha l ogen-subs ti tuted aro mati c compounds covalen tl y bound thereto is i n a range of 1 to 40 parts by weight based on 100 parts by weight of the heat -resi stant po l ymer precursors. withdrawn
(Withdrawn) A method of prepa ri ng reduced graphene oxide-polymer co m pos i tes, the method comprising: m ixing a graphene oxide and a ha l oge n- subs ti tuted aromatic compounds; stirring the m i xture to obtain a graphene o xi de with the halogen-substituted aromatic compounds cova lent ly bound thereto: mixi ng the graphene oxide with the ha l ogen-subs ti tuted aro mati c compounds cov al ent ly bound ther e to and monomers fo r p ol ymerization; and heat treat in g the mixture at a temperature i n a range of 100 to 45 0 C. withdrawn
The method of claim 16, wherein in the reduced graphe n e ox ide- polymer compos it es the po lym ers comp ri se any one of po lyol efin, po l yester, po lyamide, poly benzimidazo l e (P BI), and po ly benzoxazo l e (P B O). withdrawn
1 7. (Withdrawn) The m ethod of clai m 16, wherein an a m ount o f the h al oge n- subst i tuted aromatic compound i s in a range of 1 to 40 parts by weight based on 100 parts by weight of the monomers. Page 5 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 withdrawn
(W ithdrawn) The method of cl aim 16, wherein at l east one of a po l ymer ization catalyst, a po l yme ri zation initiator, a th e rma l sta bil izer, and an antioxidant i s further added to the mixture of the graphene o xi de with the ha l ogen-subst itu ted aromatic compounds cova lentl y bound thereto and monomers for po ly meriza ti on. withdrawn
1 9. The method of clai m 13, wherein i n the reduced graphene oxide-polymer composites the po lyme rs comprise any one o f po lyol efin, po l yester, po lyami de, pol yben zimi dazo l e (P SI), and po l ybenzoxazo l e (P BO). withdrawn
The method of c l aim 13, wherein the graphene oxide is prepar e d by trea ti ng graphite with a strong acid. withdrawn
(Withdrawn) The method of clai m 16, wherein the graphene o xi de i s prepared by trea ti ng graph i te w it h a strong acid. withdrawn
The method of cl aim 13, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds is in a range of 1 to 30 parts by weight based on 100 parts by weight of the graphe n e oxide. withdrawn
The method of clai m 16, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds i s in a range of 1 to 30 parts by w ei ght based on 100 parts by weig ht of the graphene oxide. withdrawn
(Wt hdrawn) A reduced graphene ox ide-polym er co m pos it es prepared us ing the method o f clai m 13 and having an e lect rica l conductivity i n a range of 0.01 to 1,000 S/rm
(Withdrawn) A reduced graphene ox i de-po l ymer composites prepared us ing the method of clai m 16 and having an e l ect rical conduct ivi ty i n a range of 0.01 to 1,000 S/rn. Page 7 of 9 withdrawn
Materials described outside the worked examples.
graphene oxide
halogen-substituted aromatic compound
Additional fabrication and treatment steps described in the patent.
Measurements and analyses referenced in the patent, with their drawing references.
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Electrical Conductivity | 10–100000 S/m | reduced graphene oxide |
Electrical Conductivity | 0.01–1000 S/m |
Related documents with shared materials, methods, properties, or citations.
Patent
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Patent
US 9,318,231Patent drawings and their descriptions. Click a drawing to enlarge it.
FIGS. 1 A through 1 C are schematic diagrams illustrating a structure in which a halogen- substituted aromatic compound is covalently bound to a graphene oxide …
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
(curren tl y amended) A method of prepa ri ng a reduced graphene o xi de RGO), the method comprising: mixi ng a graphene oxid e and a ha lo gen-subs tit uted aro mat ic compounds compound; stirring the mixture to obtain a graphene oxide [[with]] covalently bound to the halogen-subs ti tuted aroma tic compounds cova; ently bundthereto c ompound and heat treat i ng the graphene oxide [[with]] covalently bound to the ha logen- substi t uted aromat ic componds-covalently-bound-t heret o- comp ou nd at a temperature in a range of 100 to 45 0 C to prepare the RGO.
(curren t ly amended) The method of claim 1, wher ei n the halogen-substituted aromatic compounds-are- is a compound r epre sented by Formula 1 below: R-- Ar-L < Formu la 1> wher ei n R i s H or a ha lo gen atom, Ar i s a subs ti tuted or unsubst i tuted C 6LC₁ 4 aro matic ring, L i s -OH, -COOH, -NH2,-N₂TX-, or -NH- --- NH2, where X-is a monova l ent Page 2 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 counter anion, provided that w h e n R i s H, A r i s subst i tuted with at l east one halogen atom.
8. (curren t ly amended) The method of claim 1, wher ein [[a]] the co valent bond between that covalentl binds the graphene oxide to the ha l oge n- substituted aromatic compoundsand-the-gaphene-e x id compound i s formed on a plane or an edge of the graphene oxide.
(Orig inal) A reduced graphene o xi de prepared using the method of claim 1 and having an el ect rical conduc t ivity in a rang e of 10 to 1 00, 000 S/m. Page 6 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(Or iginal) The method of c l aim 1, wher ei n the graphene oxid e i s pr e pared by treating graphite w it h a strong acid.
(Orig ina l) The method o f cl aim 3, wherein in Formu l a 1 Ar is a pheny l ene group, a naphthy le ne group, or an anthracen yl ene group.
(current l y amended) The method of cl aim 3, wherein the ha logen- substituted SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.11.522.1427.1873.1996.svg 1.897 4.503 Chemistry Black and white aromatic compound s com p ou nd of Formul a 1 is se le cte d f rom the roup consistin one-of the-compounds-below-
SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.15.300.2164.634.2344.svg 0.60 1.113 Chemistry Black and white SVG 13410465.09-08-2015.IEE₄M₇OTPXXIFW1.CLM.2.17.300.2403.901.2645.svg 0.807 2.003 Chemistry Black and white 7. The method of clai m 1, wherein an amount of the halogen-substituted aromatic compounds compound is i n a range of 1 to 30 parts by w ei ght based on 100 parts by weight of the graphene oxide. Page 3 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660
(curren tl y amended) The method of c lai m 1, wher e in the ha lo gen-substituted aro matic compo und s- are compound is a ha logen- substi t uted aromatic hydra z ine.
(Original) The method of claim 9, where in the ha l oge n- subs ti tuted aromatic hydraz i ne form s a compound having an indol e structur e by [3,3]-sigmatrop ic rearrangement with the graphene o xi de.
1 0. (Orig inal) The method of cl aim 9, wher ei n the halogen-substituted aroma tic hydrazine is ha l oge n- substitu t ed phen yl hydraz i ne or ha loge n-substituted naphthy l hydrazine.
(curren tl y amended) The method of cl aim 1, wherein the graphene oxide [[with]] covalently bound to the ha log en-substituted aroma ti c compound covalently-baund thereto i s heat treated at a temperature ranging from 100 to 450 C [[.]], for 1 to 10 hours in a ir or in a nitrogen atmosphere.
A method of prepa ring a reduced graphene o xide-poly mer composites, the method comprising: Page 4 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 mixi ng a graphene oxide and a ha logen- subs ti tuted aro matic compounds; stirring the m ixtur e to obta in a graphene oxide wi th th e ha l oge n- substituted aromatic compounds cova lent ly bound thereto; mixi ng the graphene oxide with the halogen-subst it uted aroma tic compounds c ovalently bound thereto and a heat-resistant po lym er precursors and drying the m ix ture to obtain a graphene oxide -polym er precursor composites; and heat treating the graphene o xi de-po l ymer precursor composites at a te m perature in a range of 100 to 45 0 C. withdrawn
(Withdrawn) The method of cl aim 13, wherein the heat -resi stant polymer precursor compris e s any one of po lyami c a ci d (PAA), po l yacry l onitr il e (PAN), hydroxy l- containing polyam ic a ci d (PAA), and hydroxy l- contain i ng po l yam i de. withdrawn
1 5. (Withdrawn) The m ethod of clai m 13, wherein an a m ount o f the graphene oxide w ith the ha l ogen-subs ti tuted aro mati c compounds covalen tl y bound thereto is i n a range of 1 to 40 parts by weight based on 100 parts by weight of the heat -resi stant po l ymer precursors. withdrawn
(Withdrawn) A method of prepa ri ng reduced graphene oxide-polymer co m pos i tes, the method comprising: m ixing a graphene oxide and a ha l oge n- subs ti tuted aromatic compounds; stirring the m i xture to obtain a graphene o xi de with the halogen-substituted aromatic compounds cova lent ly bound thereto: mixi ng the graphene oxide with the ha l ogen-subs ti tuted aro mati c compounds cov al ent ly bound ther e to and monomers fo r p ol ymerization; and heat treat in g the mixture at a temperature i n a range of 100 to 45 0 C. withdrawn
The method of claim 16, wherein in the reduced graphe n e ox ide- polymer compos it es the po lym ers comp ri se any one of po lyol efin, po l yester, po lyamide, poly benzimidazo l e (P BI), and po ly benzoxazo l e (P B O). withdrawn
1 7. (Withdrawn) The m ethod of clai m 16, wherein an a m ount o f the h al oge n- subst i tuted aromatic compound i s in a range of 1 to 40 parts by weight based on 100 parts by weight of the monomers. Page 5 of 9 Application Serial No. 13/410,465 PATENT Reply to Office Action of Docket: CU-9660 withdrawn
(W ithdrawn) The method of cl aim 16, wherein at l east one of a po l ymer ization catalyst, a po l yme ri zation initiator, a th e rma l sta bil izer, and an antioxidant i s further added to the mixture of the graphene o xi de with the ha l ogen-subst itu ted aromatic compounds cova lentl y bound thereto and monomers for po ly meriza ti on. withdrawn
1 9. The method of clai m 13, wherein i n the reduced graphene oxide-polymer composites the po lyme rs comprise any one o f po lyol efin, po l yester, po lyami de, pol yben zimi dazo l e (P SI), and po l ybenzoxazo l e (P BO). withdrawn
The method of c l aim 13, wherein the graphene oxide is prepar e d by trea ti ng graphite with a strong acid. withdrawn
(Withdrawn) The method of clai m 16, wherein the graphene o xi de i s prepared by trea ti ng graph i te w it h a strong acid. withdrawn
The method of cl aim 13, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds is in a range of 1 to 30 parts by weight based on 100 parts by weight of the graphe n e oxide. withdrawn
The method of clai m 16, wherein an amount of the ha l ogen-subs ti tuted aromatic compounds i s in a range of 1 to 30 parts by w ei ght based on 100 parts by weig ht of the graphene oxide. withdrawn
(Wt hdrawn) A reduced graphene ox ide-polym er co m pos it es prepared us ing the method o f clai m 13 and having an e lect rica l conductivity i n a range of 0.01 to 1,000 S/rm
(Withdrawn) A reduced graphene ox i de-po l ymer composites prepared us ing the method of clai m 16 and having an e l ect rical conduct ivi ty i n a range of 0.01 to 1,000 S/rn. Page 7 of 9 withdrawn
Materials described outside the worked examples.
graphene oxide
halogen-substituted aromatic compound
Additional fabrication and treatment steps described in the patent.
Measurements and analyses referenced in the patent, with their drawing references.
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Electrical Conductivity | 10–100000 S/m | reduced graphene oxide |
Electrical Conductivity | 0.01–1000 S/m |
Related documents with shared materials, methods, properties, or citations.
reduced graphene oxide
graphite
halogen-substituted aromatic hydrazine
heat-resistant polymer precursor
reduced graphene oxide-polymer composite
graphene oxide with halogen-substituted aromatic compound covalently bound
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Electrical Conductivity | 30000 S/m | reduced graphene oxide |
Temperature | 100–450 °C | — |
Pressure | 1–30 pa | — |
Duration | 1–10 hours | — |
Pressure | 1–40 pa | — |
Temperature | 100–150 °C | — |
Temperature | 150–200 °C | — |
Temperature | 200–300 °C | — |
Temperature | 300–450 °C | — |
Thickness | 20–25 mm | — |
Thickness | ≤ 30 nm | — |
Temperature | ≤ 450 °C | — |
reduced graphene oxide
graphite
halogen-substituted aromatic hydrazine
heat-resistant polymer precursor
reduced graphene oxide-polymer composite
graphene oxide with halogen-substituted aromatic compound covalently bound
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Electrical Conductivity | 30000 S/m | reduced graphene oxide |
Temperature | 100–450 °C | — |
Pressure | 1–30 pa | — |
Duration | 1–10 hours | — |
Pressure | 1–40 pa | — |
Temperature | 100–150 °C | — |
Temperature | 150–200 °C | — |
Temperature | 200–300 °C | — |
Temperature | 300–450 °C | — |
Thickness | 20–25 mm | — |
Thickness | ≤ 30 nm | — |
Temperature | ≤ 450 °C | — |
reduced graphene oxide
graphite
halogen-substituted aromatic hydrazine
heat-resistant polymer precursor
reduced graphene oxide-polymer composite
graphene oxide with halogen-substituted aromatic compound covalently bound
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Electrical Conductivity | 30000 S/m | reduced graphene oxide |
Temperature | 100–450 °C | — |
Pressure | 1–30 pa | — |
Duration | 1–10 hours | — |
Pressure | 1–40 pa | — |
Temperature | 100–150 °C | — |
Temperature | 150–200 °C | — |
Temperature | 200–300 °C | — |
Temperature | 300–450 °C | — |
Thickness | 20–25 mm | — |
Thickness | ≤ 30 nm | — |
Temperature | ≤ 450 °C | — |
reduced graphene oxide
graphite
halogen-substituted aromatic hydrazine
heat-resistant polymer precursor
reduced graphene oxide-polymer composite
graphene oxide with halogen-substituted aromatic compound covalently bound
FIG. 2 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Examples 2 and 3; 15
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 3 is a graph showing Raman spectroscopic spectra of reduced graphene oxides prepared according to Comparative Examples 2 and 3;
FIG. 4 is a graph showing thermogravimetric analysis (TGA) results of reduced graphene oxides prepared according to Examples 2 and 3;
FIG. 5 is graph showing TGA results of reduced graphene oxides prepared 20 according to Comparative Examples 2 and 3;
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIG. 6 is a graph showing X-ray diffraction (XRD) results of reduced graphene oxides prepared according to Example 2 and Comparative Example 2; and
FIGS. 7A and 7B are transmission electron microscopic (TEM) images of reduced graphene oxides of Example 2 and Comparative
Electrical Conductivity | 30000 S/m | reduced graphene oxide |
Temperature | 100–450 °C | — |
Pressure | 1–30 pa | — |
Duration | 1–10 hours | — |
Pressure | 1–40 pa | — |
Temperature | 100–150 °C | — |
Temperature | 150–200 °C | — |
Temperature | 200–300 °C | — |
Temperature | 300–450 °C | — |
Thickness | 20–25 mm | — |
Thickness | ≤ 30 nm | — |
Temperature | ≤ 450 °C | — |