WO2006023419A1 - Processes for producing monolithic porous carbon disks from aromatic organic precursors - Google Patents
Processes for producing monolithic porous carbon disks from aromatic organic precursors Download PDFInfo
- Publication number
- WO2006023419A1 WO2006023419A1 PCT/US2005/028890 US2005028890W WO2006023419A1 WO 2006023419 A1 WO2006023419 A1 WO 2006023419A1 US 2005028890 W US2005028890 W US 2005028890W WO 2006023419 A1 WO2006023419 A1 WO 2006023419A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon
- precursor
- polyimide
- aromatic
- porous carbon
- Prior art date
Links
- 239000002243 precursor Substances 0.000 title claims abstract description 112
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 99
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 86
- 230000008569 process Effects 0.000 title claims abstract description 52
- 125000003118 aryl group Chemical group 0.000 title claims description 43
- 229920001721 polyimide Polymers 0.000 claims abstract description 96
- 239000004642 Polyimide Substances 0.000 claims abstract description 94
- 239000000843 powder Substances 0.000 claims abstract description 87
- 229920002480 polybenzimidazole Polymers 0.000 claims abstract description 46
- 239000004693 Polybenzimidazole Substances 0.000 claims abstract description 45
- 239000002131 composite material Substances 0.000 claims abstract description 18
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000654 additive Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- -1 aromatic tetracarboxylic acids Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000007513 acids Chemical class 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 18
- 239000000835 fiber Substances 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000011148 porous material Substances 0.000 claims description 15
- 238000000197 pyrolysis Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 14
- 239000003990 capacitor Substances 0.000 claims description 13
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229920000768 polyamine Polymers 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000004984 aromatic diamines Chemical class 0.000 claims description 10
- 238000007596 consolidation process Methods 0.000 claims description 10
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 9
- 229910000765 intermetallic Inorganic materials 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical group 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 8
- 229910052750 molybdenum Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 229920003002 synthetic resin Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 claims description 4
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007772 electrode material Substances 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- 239000002952 polymeric resin Substances 0.000 claims description 3
- IGUXFXNMXMXLCK-UHFFFAOYSA-N (3-aminophenyl)-(3,4-diaminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C(N)=CC=2)=C1 IGUXFXNMXMXLCK-UHFFFAOYSA-N 0.000 claims description 2
- YKAVPKYCQOKDAP-UHFFFAOYSA-N (3-aminophenyl)-(3,4-diaminophenyl)methanone;trihydrochloride Chemical compound Cl.Cl.Cl.NC1=CC=CC(C(=O)C=2C=C(N)C(N)=CC=2)=C1 YKAVPKYCQOKDAP-UHFFFAOYSA-N 0.000 claims description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 2
- ILPWTQGYOZFLBN-UHFFFAOYSA-N 4-[(3,4-diaminophenyl)methyl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1CC1=CC=C(N)C(N)=C1 ILPWTQGYOZFLBN-UHFFFAOYSA-N 0.000 claims description 2
- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- BZDGCIJWPWHAOF-UHFFFAOYSA-N benzene-1,2,4,5-tetramine;hydron;tetrachloride Chemical compound Cl.Cl.Cl.Cl.NC1=CC(N)=C(N)C=C1N BZDGCIJWPWHAOF-UHFFFAOYSA-N 0.000 claims description 2
- NOZDKQWTDYQXDO-UHFFFAOYSA-N benzene-1,2,4-triamine;trihydrochloride Chemical compound Cl.Cl.Cl.NC1=CC=C(N)C(N)=C1 NOZDKQWTDYQXDO-UHFFFAOYSA-N 0.000 claims description 2
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- NLNRQJQXCQVDQJ-UHFFFAOYSA-N bis(3,4-diaminophenyl)methanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=C(N)C(N)=C1 NLNRQJQXCQVDQJ-UHFFFAOYSA-N 0.000 claims description 2
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 claims description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
- UIMPSNPKHVULAQ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetramine Chemical compound NC1=C(N)C=CC2=C(N)C(N)=CC=C21 UIMPSNPKHVULAQ-UHFFFAOYSA-N 0.000 claims description 2
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 2
- DKYADULMEONPQX-UHFFFAOYSA-N naphthalene-2,3,6,7-tetramine Chemical compound NC1=C(N)C=C2C=C(N)C(N)=CC2=C1 DKYADULMEONPQX-UHFFFAOYSA-N 0.000 claims description 2
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 claims description 2
- IQDQMRZGMILNMQ-UHFFFAOYSA-N naphthalene-2,6-dicarbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(C=O)=CC=C21 IQDQMRZGMILNMQ-UHFFFAOYSA-N 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 239000012779 reinforcing material Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 claims 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims 1
- UYIWPVOKZZKUMC-UHFFFAOYSA-N 4-(3,4-diaminophenyl)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1.C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 UYIWPVOKZZKUMC-UHFFFAOYSA-N 0.000 claims 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims 1
- 229920000914 Metallic fiber Polymers 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- AZVOEEHCPIRDBR-UHFFFAOYSA-N bis(3,4-diaminophenyl)methanone;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C1=C(N)C(N)=CC=C1C(=O)C1=CC=C(N)C(N)=C1 AZVOEEHCPIRDBR-UHFFFAOYSA-N 0.000 claims 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 claims 1
- 239000002041 carbon nanotube Substances 0.000 claims 1
- 229910021393 carbon nanotube Inorganic materials 0.000 claims 1
- 229910052735 hafnium Inorganic materials 0.000 claims 1
- 239000011256 inorganic filler Substances 0.000 claims 1
- 229910003475 inorganic filler Inorganic materials 0.000 claims 1
- 229920000592 inorganic polymer Polymers 0.000 claims 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 claims 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims 1
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- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
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- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
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- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- 239000004966 Carbon aerogel Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- 230000007704 transition Effects 0.000 description 4
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
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Classifications
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- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
- C04B35/524—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from polymer precursors, e.g. glass-like carbon material
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- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- H01M4/8647—Inert electrodes with catalytic activity, e.g. for fuel cells consisting of more than one material, e.g. consisting of composites
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- C04B2235/96—Properties of ceramic products, e.g. mechanical properties such as strength, toughness, wear resistance
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
- H01M4/624—Electric conductive fillers
- H01M4/625—Carbon or graphite
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Definitions
- the present invention relates to the preparation of precursors composed of either or both polyimide and polybenzimidazole as organic precursors for producing monolithic porous carbon with density less than or equal to 1.0 g/cc; and the processes for producing monolithic porous carbon from either or both polyimide and polybenzimidazole precursors in the powder form.
- the present invention further relates to the processes for producing monolithic porous carbon derived from either or both polyimide and polybenzimidazole precursors having one or more than one metals dispersed therein.
- the present invention even further relates to the processes for producing carbon-carbon composite prepared from precursors comprising either or both polyimide and polybenzimidazole and activated carbon in the form of powders and/or fibers.
- Monolithic porous carbon which possess interpenetrating pore structure, high density, high surface area, suitable pore size, and well defined pore size distribution, are highly desirable as electrode materials for lithium batteries, electrochemical capacitors, fuel cells, as well as other electrochemical devices.
- the following description will be directed to disk products although it will be understood that other such products can be made from the porous carbon.
- One approach to produce monolithic porous carbon disk is through sol-gel technologies.
- the sol-gel technology generally consists of preparation of gels from solution, drying the gel while minimizing the gel shrinkage. The pyrolysis of thin gel films yields porous monolithic carbon disks.
- RF carbon aerogel currently in the market as electrode material for supercapacitors is derived from resorcinol and formaldehyde organic precursors.
- RF carbon aerogel provide high surface area and narrow pore size distribution.
- the present invention provides processes for producing monolithic porous carbon, e.g., disks, from a group of aromatic organic precursors comprising either or both polyimide or polybenzimidazole.
- the processes include the steps of: (1) preparation of the organic precursors in the powder form; (2) consolidation of the powders into a monolith; (3) pyrolysis producing a monolithic porous carbon product such as a disk.
- the present invention further provides processes for producing monolithic porous carbon disks doped with transition metals from a group of aromatic organic precursors comprising either or both polyimide or polybenzimidazole and metallic compounds.
- the processes include the steps of: (1) preparation of the precursors in- situ doped with metallic compounds in the powder forms; (2) consolidation of the powders into a monolith; (3) pyrolysis producing monolithic porous carbon product such as a disk.
- the present invention even further provides processes for producing porous carbon-carbon composite from the precursors of this invention and carbon in the forms of powders, or fibers, or nanotubers, or bulky balls (C60, or C70, or others), or fullerenes, or a mixture thereof.
- the carbon that is used in the present processes is activated carbon powder and activated carbon fiber.
- the processes include the steps of: (1) preparation of the precursors either in the powder form or a viscous solution; (2) blending together the carbon and the precursor in which the case of the solvent is removed after mixing; (3) consolidation of the mixture into a monolith; (4) pyrolysis producing a porous carbon-carbon composite.
- the organic precursors of this invention have nitrogen-containing heterocyclic structures that connect monomer units into rod-like molecular chain structures with few flexible links or hinges.
- the chain architecture of the precursors consists of either linear chains, or a three-dimensional network, or hyberbranched chain structure.
- One group of the precursors comprises polyimide with imide group in the molecular structure.
- Another group of the precursors comprises polybenzimidazole with benzimidazole group in the molecular structure.
- another group of the precursors comprises both polyimide and polybenzimidazole with both imide and benzimidazole groups in the molecular structure.
- the monolithic porous carbon disks produced from this invention can be further reinforced by fibers or fiber pads or other additive by incorporating fibers, inorganic or organic particles, fiber pads, or other additives during the compression molding process.
- the precursor powders may be further assembled with other additives in addition to carbon before consolidation into a monolith.
- additives include transition metal oxide powders, organic particles, inorganic particles, graphite fibers or flakes, metal fibers, porous substrates including membranes, metallic meshes, carbon cloth, carbon felt, foams, and polymeric resins, such as phenolic resins and commercial polyimide resins.
- the precursors prepared from the aromatic organic monomers of this invention may comprise other components in the molecular chain structure, such as polybenzimidazole, polyamide, polyetherimide, siloxane, or silica, but have the polyimide and aromatic organic composition preferably greater than or equal to 50% by weight.
- the polyimide and polybenzimidazole may be represented by the formulas:
- Al and A4 represent difunctional phenyl, difunctional biphenyl, an optionally substituted difunctional aryl, optionally substituted difunctional alkylene, an optionally substituted difunctional heteroaryl, or a combination thereof; wherein A2 and A5 represents tetra functional phenyl, biphenyl, an optionally substituted tetra functional aryl group, or an optionally substituted heteroaryl group; wherein A3 represent multifunctional phenyl with functionality more than or equal to 2, multifunctional biphenyl with functionality more than or equal to 2, an optionally substituted multifunctional aryl with functionality more than or equal to 2, optionally substituted multifunctional alkylene with functionality more than or equal to 2, an optionally substituted multifunctional heteroaryl with functionality more than or equal to 2, or a combination thereof; n1 , n2 and n3 are greater or equal to 1 ; and (y+2) are more than or equal to 2.
- One application of this invention is to provide a novel carbon electrode for use in electrochemical capacitors, batteries, and fuel cells.
- Another application of this invention is to provide a novel composite of carbon and transition metal oxides, such as MnO2, as an electrode for use in lithium batteries or hybrid -battery/electrochemical capacitor systems.
- Another application of this invention is to provide a catalytic carbon support for use in fuel cells and electrochemical water purification systems.
- Fig. 1 is a cyclic voltammetry (CV) graph of Example 1 showing C (F/gram) versus voltage at a scan rate of 5 mV/sec.
- Fig. 2 is a cyclic voltammetry (CV) graph of Example 2 showing C (F/gram) versus Voltage at a scan rate of 5m V/sec.
- Fig. 3 is a cyclic voltammetry (CV) graph of Example 3 showing C (F/gram) versus Voltage at a scan rate of 5m V/sec.
- Fig. 4 is impedance data of Samples 9a and 9b at 0.75 V bias level with the sulfuric acid electrolyte. ( — black) from Sample 9a and ( — red) from the capacitor with Sample 9b. Mode(s) for Carryout Out the Invention
- the present invention provides processes for producing monolithic disks comprising either or both polyimide and polybenzimidazole as organic precursors for producing monolithic porous carbon which have surface area at or above 500 mVgram and sufficiently high mechanical strength.
- aromatic monomers for preparing polyimide precursors of this invention are preferably selected from one of the following groups: aromatic dianhydride, aromatic diamine, and as an option, an aromatic polyamine compounds with amine functionality beyond 2; or aromatic tetracarboxylic acids, aromatic diamine, and as an option, an aromatic polyamine compounds with amine functionality beyond 2; or ester(s) of aromatic tetracarboxylic acids, aromatic diamine, and as an option, an aromatic polyamine compounds with amine functionality beyond 2; or aromatic dianhydride, aromatic isocyanates including diisocyanate and polyisocyanate with functionality beyond 2.
- the aromatic monomers for preparing polybenzimidazole precursors are preferably selected from one of the following monomer groups: aromatic dialdehydes and aromatic tetraamines; or diesters of aromatic dicarboxylic acids and aromatic tetraamines; or aromatic dicarboxylic acids and aromatic tetraamines.
- the precursors comprising either or both polyimide and polybenzimidazole can preferably be synthesized from the monomers either in the presence of a solvent or in the melt state by the following procedures:
- the precipitate could be either a precipitated powder or a precipitated film onto another solid substrate.
- the solvent in the precursors is removed by distillation, assisted by vacuum if it is necessary.
- the precursors are further ground into fine powder or porous particles, filtered through a sieve if it is necessary.
- the polyimide precursors are preferably condensation products of aromatic diamines and aromatic tetracarboxylic dianhydride, or aromatic diamines and tetracarboxylic acids, or aromatic diamines and ester(s) of tetracarboxylic acids, or aromatic isocyanates and aromatic tetracarboxylic dianhydride.
- a small amount of polyamine compounds with amine functionality greater than two takes the place of some of the aromatic diamine to introduce chemical cross-links to the polyimide precursors. Therefore, polyimide precursors may possess linear molecular structure, or a hyper-branched molecular structure, or a three-dimensional network molecular structure.
- the synthesis of polyimide precursors generally proceeds in the synthesis of poly(amic acids) and then imidization to form polyimide.
- Procedure 1 the monomers and other additives are dissolved in a solvent to form a clear solution.
- the precursors in the form of fine powders are either a homogeneous mixture of monomers or a mixture of low molecular weight oligomers of polyimide and poly(amic acids).
- Procedure 2 the monomers and other additives are dissolved in an organic solvent. The reaction is carried out with a normal agitation at or above 100 0 C, preferably at or above 150 0 C 7 to produce polyimide precipitate.
- the polyimide precursors are in the form of either precipitated powder or gels.
- the solvent is removed from the product by distillation, assisted by vacuum if it is necessary.
- the esters of tetracarboxylic acids and aromatic amines are the monomers of choice.
- the condensation reaction at molten state of monomers releases phenol or an alcohol molecule in the gas phase to produce rigid polyimide foams.
- the product is further ground to produce polyimide powder.
- polyimide precursor is carried out according to Procedure 2 in two steps: synthesis of poly(amic acids) and imidization to form polyimide.
- the synthesis of poly(amic acids) is conducted by dissolving monomers and other additives in an organic solvent at ambient temperature with a normal agitation for a time period from several hours to overnight to yield product in the forms of either precipitated powder or viscous liquid solution or gels.
- the imidization of poly(amic acids) to form polyimide is carried out by either chemical imidization at ambient temperature or thermal imidization at elevated temperatures.
- the chemical imidization is conducted by addition of dehydrating agents to poly(amic acids).
- dehydrating agents are added before the reaction solvent is removed from the system.
- the addition of dehydrating agents to poly(amic acids) solution is carried out in such a way that the reaction at ambient temperature yields polyimide precipitate.
- the solvent is removed from the polyimide precipitate by distillation.
- the dehydrating agents consists of either an acid anhydride or a mixture of an acid anhydride and an organic base.
- Preferred acid anhydrides include acetic anhydride, propionic anhydride, n-butyric anhydride, benzoic anhydride, and trifluoroacetic anhydride.
- Preferred organic bases include optionally substituted mono-, di-, tri alky I amines, and optionally substituted pyridines.
- the thermal imidization is conducted at elevated temperatures.
- the solvent is removed by distillation followed by a thermal imidization of poly(amic acids) powder at a temperature in the range of 5O 0 C to 500 0 C preferably in the range of 100 0 C to 400 0 C and preferably under protection of an inert gas, such as nitrogen or argon.
- an inert gas such as nitrogen or argon.
- the imidization is conducted at elevated temperatures in the range of 50 0 C to 400 0 C, preferably in the range of 100 0 C to 250 0 C to produce polyimide in the form of precipitated powder.
- the solvent is removed by distillation, assisted by vacuum if it is necessary.
- the synthesis of polyimide precursors is preferably carried out according to Procedure 1.
- the monomers and additives are admixed at ambient temperature in the presence of preferably a dipolar aprotic organic solvent. The solvent removal produces a homogeneous mixture in the powder form.
- polyimide precursors are prepared from aromatic monomers of tetracarboxylic dianhydride, aromatic diamine, and optionally, a polyamine compound according to Procedure 2 using thermal imidization method.
- the reaction of monomers and other additives are conducted in an organic solvent, such as di methyl acetamide (DMAc), at ambient temperature with agitation for a period of time.
- Temperature of the reaction system is then raised to the range of 13O 0 C to 200 0 C, preferably in the range of 150 0 C to 180 0 C to produce polyimide as precipitate.
- the solvent is distilled off to produce the dried polyimide precursor powder.
- the polybenzimidazole precursors are preferably condensation products of aromatic tetraamines and aromatic esters of dicarboxylic acids, or aromatic tetraamines and aromatic dialdehyde.
- the synthesis proceeds either in the molten state of monomers or in the presence of a solvent.
- aromatic tetraamine and aromatic dialdehyde as aromatic monomers the synthesis of polybenzimidazole is carried out according to Procedure 2 in two- stages: synthesis of poly(azomethines) as intermediate product in the presence of an organic solvent and synthesis of poly(benzimidazole).
- the reaction of the monomers in an organic solvent is carried out at temperatures in the range of -30 0 C and ambient temperature to produce poly(azomethines) in the forms of either precipitated powder or viscous liquid solution. Further reaction at an elevated temperature in the range of 5O 0 C to 35O 0 C, more preferably in the range of 100 0 C to 250 0 C, converts poly(azomethines) to polybenzimidazole.
- the solvent is removed from the system when the product precipitated from the solution either before or after second stage reaction at elevated temperatures.
- polybenzimidazole proceeds preferably according to Procedure 3 in the molten state of the monomers although not exclusive to the synthesis in the presence of a solvent.
- the reactions are conducted at or above melting temperatures of the monomers with strong agitation and in such conditions that side products of phenol, or water, or an alcohol in the gas phase are released from the system to produce the product in foams.
- the products are crushed and further ground to produce polybenzimidazole precursors in the form of porous powder.
- the precursors comprising both polyimide and polybenzimidazole segments in the molecular structure can be prepared preferably in the presence of an organic solvent.
- the synthesis can be conducted by either synthesizing one precursor of either polyimide or polybenzimidazole before adding the monomers for the other precursor to the reaction system. Or the reactions of polyimide and polybenzimidazole are carried out separately before combining two reactions into one reaction system. Or two sets of the monomers are mixed together simultaneously in the same reaction solution when the reaction conditions are compatible. Yet, such mixing would be generally prohibited if a relatively large amount of flexible amide links were introduced to the molecular chain structure so as to reduce the glass transition temperature of the material significantly.
- An alternative approach to prepare monolithic porous carbon disks from precursors comprising both polyimide and polybenzimidazole is mixing both powders of polyimide and polybenzimidazole precursors together during the process of consolidating the powders into a monolith disk.
- the precursor powders comprising either or both polyimide and polybenzimidazole are further broken down to smaller particle size by a shear stress and filtered through a sieve if it is necessary.
- the preferred particle size of precursors for the purpose of compression molding is in the range of 1//m to 300/zm, more preferably in the range of 5 ⁇ m to 75 ⁇ m, even more preferably in the range of 10 ⁇ m to 50 ⁇ m.
- the precursor powder comprising either or both polyimide and polybenzimidazole in the powder form is further thermally annealed at elevated temperatures before consolidating into a disk.
- the annealing is conducted in a temperature range of 5O 0 C to 600 0 C, more preferably in the range of 50 0 C to 500 0 C for a time period between 20 minutes to 2 hours under vacuum or under protection of argon or nitrogen atmosphere.
- the present invention provides processes for producing porous monolithic disks of transition metal doped precursors comprising either or both polyimide and polybenzimidazole as organic precursors for producing transition metal doped monolithic porous carbon disks which have surface area at or above 500 nrvVgram, sufficiently high mechanical strength, and macrocyclic pyridine structure wherein the transition metal atoms caged or complexed into to provide catalytic activities.
- a transition metallic compound in solution is added to the reaction system or to the dried precursor powder or to the dried disk precursor.
- the solvent used for dissolving the transition metallic compound is preferably the same solvent as the one for preparing the precursors.
- the transition metallic compounds are added during the early stages of the procedures. Even more preferably, the transmission metallic compounds are admixed with the organic precursors in the presence of an organic solvent before proceeding with the synthesis of the precursors.
- the solvent removal during the synthesis of the precursors comprising either or both of polyimide and polybenzimidazole are conducted by distillation, preferably assisted by vacuum.
- Metals suitable for use in the preparation of metal doped monolithic porous carbon of this invention are not limited and may include elemental metals, organometallic compounds, coordination inorganic compounds, metal salts or any combinations thereof.
- the preferred metals include Ti, Zr, V, Nb, Cr, Mo, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Cu, Ag, Zn, Si, Sn, Pb, Sb, Nb, Bi, Hf, Ba, Al, B, P As, Li and combinations thereof.
- Exemplary transition metal compounds include cobalt chloride (CoCb), iron chloride (FeCb), nickel chloride (NiCb), molybdenum chloride (MoCIs), hydrogen hexachloroplatinate hydrate (H2PtCl6*xH2 ⁇ ), copper chloride (CuCb), tungsten chloride (WCI ⁇ ), zirconium chloride (ZrCU), cerium nitrate (Ce(NO3)3), ruthenium chloride (RuCb) and hafnium chloride (HfCU).
- CoCb cobalt chloride
- FeCb iron chloride
- NiCb nickel chloride
- MoCIs molybdenum chloride
- H2PtCl6*xH2 ⁇ hydrogen hexachloroplatinate hydrate
- CuCb copper chloride
- WCI ⁇ tungsten chloride
- ZrCU zirconium chloride
- Ce(NO3)3 cerium nitrate
- RuCb ruthenium
- the transition metallic compound is present in the precursor in an amount from 0.01 % to 20% by weight, or more.
- the present invention provides processes for producing monolithic porous carbon disks which has a rod density of less than or equal to 1.0 gram/cc comprising: producing the organic precursors in powders comprising either or both polyimide and polybenzimidazole; consolidation of the powder into a monolith under a pressure in the range of 3000 psi to 13000 psi; and pyrolysis under protection of an inert atmosphere.
- the present invention provides processes for producing monolithic porous carbon having one or more than one metals dispersed therein, which has a rod density of less than or equal to 1.0 gram/cc comprising: powders of transition metal doped precursors comprising either or both polyimide and polybenzimidazole; consolidation of the porous precursor powders into a monolith preferably at ambient temperature under a pressure in the range of 3000 psi to 13000 psi. and pyrolysis under protection of an inert atmosphere.
- the precursor powders are evenly placed in a mold or on a supporting substrate such as a fiber pad, before a sufficiently high compression pressure and a sufficient holding time are applied to produce a monolith disk with rod density in the range of 0.4g/c to 1.Og/c, preferably 0.6g/cc to 0.95g/cc.
- Pyrolysis of the compressed disks is carried out under protection of an inert gas atmosphere, such as argon, nitrogen or carbon dioxide, at a temperature in the range of 600 0 C to 3000 0 C, more preferably 750 0 C to 1500 0 C.
- an inert gas atmosphere such as argon, nitrogen or carbon dioxide
- the inert gas atmosphere may be changed to carbon dioxide during the pyrolysis, preferably in the later stage of the pyrolysis, to further activate the pore surface of the monolithic carbon disk.
- the heating rate shall be sufficiently slow as to optimize the properties of the monolithic carbon.
- the present invention provides processes for producing porous carbon-carbon composite with a rod density of less than or equal to 1.0 gram/cc from the precursors comprising either or both polyimide or polybenzimidazole and activated carbon in the forms of powder and fiber comprising: blending the precursor, carbon, and other additives thoroughly; removing the solvent in the mixture in cases that a solvent is involved in the mixture; consolidating the mixture into monolith under pressure conditions as to produce a homogeneous composition with desired rod density; and pyrolysis under an inert atmosphere for producing monolithic porous carbon.
- the present invention provides processes for producing porous carbon composites incorporating other additives in addition to the carbon comprising: blending the organic precursor of this invention, carbon, and other additives thoroughly; removing the solvent in the mixture in cases that a solvent is involved during the mixing; consolidating the mixture into monolith under pressure conditions as to produce a homogeneous composition with desired rod density; and pyrolysis under an inert atmosphere for producing monolithic porous carbon.
- additives include metallic compounds, silica, carbon in the forms of powders, fibers, nanotubes, and bulkyballs or fullerences, graphite, metal oxides and metal carbides, polymeric resins in either liquid or powder forms, such as commercial phenolic resins and commercial polyimide resins, and mixtures thereof.
- the additives can be in the forms of powders, fibers, flakes, liquids, or porous substrates composed of one or more than one kind of fibers, membranes, metallic meshes, and foams.
- polyimide precursors there are different ways to blend the polyimide precursor, carbon, and other ingredients together.
- one way of blending is to thoroughly mix polyimide powder with the carbon and other additives.
- Another way is to coat viscous solution of poly(amic acid) onto carbon and other additives before removing the solvent, then converting poly(amic acids) to polyimides.
- the present invention is directed in one aspect to simply mixing the polyimide precursor powder with the carbon and other additives, but is not intended to be limited to any particular way of blending the precursor with the carbon as well as other additives.
- the organic precursors comprising either or both polyimide and polybenzimidazole suitable for use in the method of making monolithic porous carbon disks of the present invention can incorporate other components during the synthesis, such as imidazopyrrolone, siloxane, silica, epoxy, bismaleimide, polyetherimide, but have the composition of polyimide and/or polybenzimidazole preferably greater than or equal to 70% by weight.
- Preferred aromatic tetracarboxylic dianhydride, or tetracarboxylic acids, or diester(s) of tetracarboxylic acids monomers suitable for use in the method of making polyimide precursors of the present invention include following dianhydride compounds and their derivatives of tetracarboxylic acids and dialkyl ester(s) of tetracarboxylic acids: pyromellitic dianhydride; pyromellitic tetracarboxylic acids, dialkyl ester(s) of pyromellitic tetracarboxylic acids and aromatic tetracarboxylic dianhydride or tetracarboxylic acids or esters of the tetracarboxylic acids including 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-benzophenone dianhydride, 2,3,6,7-naphthylene tetracarbox
- ester(s) are alkyl esters
- the alkyl group preferably contains 1 to 5 carbon atoms and is more preferably methyl.
- Preferred aromatic diamine monomers suitable for use in the methods of making polyimide precursors of the present invention include 1 ,4-phenylene diamine, m-phenylene diamine, 4,4'diamino-biphenyl, 4,4' and 3,3'- diaminodiphenylmethanes, 4,4', and 3,3' -diaminobenzophenones, benzidine, 2,6 - diaminopyridine, 2,6-diaminonaphthalene, 1,4-diaminocyclohexane, 2,4 and 2,6 - diaminotoluene, and derivatives thereof (i.e.: substituted diamine having a substituent(s)).
- the above diamine monomers may be used alone or as a mixture of two or more of them.
- Preferred polyamine compounds with amine functionality greater than 2 suitable for use in the methods of making polyimide precursors of the present invention include 3,3'4,4'-biphenyltetraamine (TAB), 1 ,2,4,5-benzenetetraamine, 3,3'4,4'-tetraaminodiphenyl ether, 3,3'4,4'-tetraaminodiphenylmethane, 3,3',4,4'- tetraaminobenzophenone, 3,3',4-triaminodiphenyl, 3,3',4-triaminodiphenylmethane, 3,3',4-triaminobenzophenone, 1 ,2,4-triaminobenzene, their mono-, di-, tri-, or tetra- acid salts., such as 3,3'4,4'-biphenyltetraamine tetrahydrochloride, 1,2,4,5- benzenetetraamine tetrahydrochloride,
- Preferred polyamine compounds with amine functionality greater than 2 suitable for use in the methods of making polyimide precursors composed of a three- dimensional molecular structure of the present invention also include a polyamine oligomer with the formula:
- Preferred aromatic isocyanate monomers suitable for use in the methods of making polyimide precursors of the present invention include 1 ,3-phenylene diisocyanate, 1 ,4-phenylene diisocyanate, 4 / 4'-diphenylmethane diisocyanate. Any of the above compounds may be used either alone or as a mixture of two or more of them.
- Preferred aromatic dialdehyde monomers suitable for use in the methods of making polybenzimidazole precursors of the present invention include isophthalaldehyde, terephthaldicarboxaldehyde, phthalic dicarboxaldehyde, and 2,6-naphthalenedicarboxaldehyde.
- Preferred monomers of aromatic acids and esters of dicarboxylic acids suitable for use in the methods of making polybenzimidazole precursors of the present invention include acids and esters of isophthalic acid, phthalic acid, terephthalic acid, 1 ,4-naphthalenedicarboxylic acid, and 2,6- naphthalenedicarboxylic acid.
- the ester(s) may be alkyl or phenyl esters. When ester(s) are alkyl esters the alkyl group preferably contains 1 to 5 carbon atoms and is more preferably methyl.
- Preferred monomers of aromatic tetraamines suitable for use in the methods of making polybenzimidazole precursors of the present invention include 3,3' ',4,4'- tetraaminobiphenyl (3,3'-dianninobenzidine); 1 ,2,4,5-tetraaminobenzene; 1, 2,5,6- tetraaminonaphthalene; 2,3,6,7-tetraaminonaphthalene; 3,3 ',4,4'- tetraaminodiphenyl methane; 3,3',4,4'-tetraaminodiphenyl ethane; 3,3',4,4'- tetraaminodiphenyl-2,2-propane; and combinations thereof.
- Preferred reaction solvents for the synthesis of the precursors comprising either or both polyimide and polybenzimidazole include N-methyl-2-pyrrolidinone (NMP), N,N-dimethylacetamide (DMAc), tyN-dimethyl formamide (DMF), tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), acetone, methanol, toluene, chlorobenzene, ethanol, and mixtures thereof.
- NMP N-methyl-2-pyrrolidinone
- DMAc N,N-dimethylacetamide
- DMF tyN-dimethyl formamide
- THF tetrahydrofuran
- DMSO dimethyl sulfoxide
- acetone acetone
- methanol toluene
- chlorobenzene chlorobenzene
- ethanol dimethyl sulfoxide
- the monolithic carbon of this invention is suitable for use as an electrode material in electrochemical capacitors
- TAB 3,3'4,4'-biphenyltetraamine
- PMDA 1,2,4,5- benzenetetracarboxylic dianhydride
- PPD 1,4-phenylenediamine
- the powders were further broken down and filtered through a 50 micron-sized sieve.
- the polyimide powders were placed in a mold and compressed under pressure of 5000 psi at ambient temperature to produce a monolithic disk.
- the monolithic disk was pyrolyzed at 800 0 C for 3 hours under protection of nitrogen to produce a monolithic carbon disk.
- the cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 90 F/gram. See Figure 1.
- TAB 3,3'4,4'-biphenyltetraamine
- PMDA 1,4-phenylenediamine
- V molybdenum chloride
- the polyimide powders were consolidated at 4500 psi pressure at ambient temperature to produce a monolithic disk.
- the monolithic disk was pyrolyzed at 800 0 C for 3 hours under protection of a nitrogen to produce a monolithic carbon disk.
- the cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 210 F/gram. See Figure 2.
- the polyimide powders were consolidated at 4500 psi pressure at ambient temperature to produce a monolith. Pyrolysis of the monolith was carried out at 800 0 C for 2 hours under a nitrogen atmosphere and 1 hour under a carbon dioxide atmosphere. The cyclic voltammetry of the carbon disk at a scan rate of 5mV/s, shown in Figure 3, displayed the capacitance of the material at 200 F/gram.
- TAB 3,3'4,4'-biphenyltetraamine
- PMDA 1,2,4,5- benzenetetracarboxylic dianhydride
- PPD 1,4-phenylenediamine
- V molybdenum chloride
- the monolithic disk was pyrolyzed at 800 0 C for 3 hours under protection of nitrogen to produce a monolithic carbon disk.
- the cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 100 F/gram.
- Example 5 Synthesis of Polyimide Precursor with three-dimensional molecular structure doped with 1% Molybdenum by weight and Carbon Disk therefrom Starting monomers and additive: 3,3'4,4'-biphenyltetraamine (TAB), 1 ,2,4,5- benzenetetracarboxylic dianhydride (PMDA), 1,4-phenylenediamine (PPD), diaminopyridine, and molybdenum chloride (V) (MoCl5).
- TAB 3,3'4,4'-biphenyltetraamine
- PMDA 1 ,2,4,5- benzenetetracarboxylic dianhydride
- PPD 1,4-phenylenediamine
- V molybdenum chloride
- the polyimide powder were compressed at 4000 psi pressure at ambient temperature to produce a monolithic disk.
- the monolithic disk was pyrolyzed at 800 0 C for 3 hours under protection of nitrogen to produce a monolithic carbon disk.
- the cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 100 F/gram.
- the polyimide powders were consolidated at 4500 psi pressure at ambient temperature to produce a monolith. Pyrolysis of the monolith was carried out at 900 0 C for 3 hours under a nitrogen atmosphere. The cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 80 F/gram.
- a supercapacitor was constructed using the carbon prepared according to Example 3 as electrodes.
- the electrode dimension was 0.81 " in diameter and 0.012" in thickness.
- the prototype supercapacitor comprises a pair of carbon electrodes sandwiched between two current collector plates.
- a microporous separator was placed between two electrodes. 38% sulfuric acid electrolyte impregnates the electrodes and the separator before the current plates were sealed by a thermoplastic edge sealant. The result of characterization is shown in Table 1 ,
- Example 8 Synthesis of Polyimide Precursor doped with 0.5% Molybdenum and Porous Carbon therefrom Starting monomers and additive: 1 ,2,4,5-benzenetetracarboxylic dianhydride (PMDA), 1 ,4-phenylenediamine (PPD), and molybdenum chloride (V) (MoCI5).
- PMDA 1,2,4,5-benzenetetracarboxylic dianhydride
- PPD 1 ,4-phenylenediamine
- V molybdenum chloride
- the polyimide powders were compressed at 4500 psi pressure at ambient temperature to produce a monolith.
- the monolith was pyrolyzed at 900 0 C for 3 hours under protection of nitrogen to produce a monolithic carbon.
- the cyclic voltammetry of the carbon disk at a scan rate of 5mV/s displayed the capacitance of the material at 150 F/gram.
- Polyimide precursor prepared in Example 6.
- Carbon Black Powder commercially available carbon black from a natural source
- Activated Carbon fiber phenolic resin based carbon fiber.
- Example 9b A Comparative Electrochemical Capacitor Cell Using Carbon Black Electrodes
- Example 10 Preparation of Carbon-Carbon Composite doped with 0.85% Molybdenum and An Electrochemical Capacitor Cell Therefrom Polyimide precursor: prepared in Example 1.
- Carbon Black Powder commercially available carbon black from a natural source
- Activated Carbon fiber phenolic resin based carbon fiber
- Molybdenum chloride (V) Molybdenum chloride (MoCl5).
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EP05808801A EP1789364A4 (en) | 2004-08-16 | 2005-08-12 | Processes for producing monolithic porous carbon disks from aromatic organic precursors |
CN200580028188XA CN101006007B (en) | 2004-08-16 | 2005-08-12 | Processes for producing monolithic porous carbon disks from aromatic organic precursors |
JP2007527902A JP2008509876A (en) | 2004-08-16 | 2005-08-12 | Method for producing monolithic porous carbon disks from aromatic organic precursors |
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US10/919,450 US7704422B2 (en) | 2004-08-16 | 2004-08-16 | Process for producing monolithic porous carbon disks from aromatic organic precursors |
US10/919,450 | 2004-08-16 | ||
US11/202,989 | 2005-08-11 | ||
US11/202,989 US7919024B2 (en) | 2004-08-16 | 2005-08-11 | Processes for producing monolithic porous carbon disks from aromatic organic precursors |
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Cited By (5)
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JP2009196839A (en) * | 2008-02-20 | 2009-09-03 | Toyota Central R&D Labs Inc | Method for producing porous carbon article and electricity storage device |
US8414805B2 (en) | 2004-08-16 | 2013-04-09 | Electromaterials, Inc. | Porous carbon foam composites, applications, and processes of making |
US9000449B2 (en) | 2009-09-07 | 2015-04-07 | The University Of Tokyo | Semiconductor substrate, method for producing semiconductor substrate, substrate for semiconductor growth, method for producing substrate for semiconductor growth, semiconductor element, light-emitting element, display panel, electronic element, solar cell element, and electronic device |
CN114634229A (en) * | 2022-04-07 | 2022-06-17 | 湖南工学院 | Adsorption electrode material with porous microsphere morphology and preparation method and application thereof |
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JP5354151B2 (en) * | 2008-05-16 | 2013-11-27 | 宇部興産株式会社 | Carbonaceous material production method, carbonaceous material, and particulate carbonaceous material |
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CN103282984A (en) * | 2010-11-26 | 2013-09-04 | 巴斯夫欧洲公司 | Process for manufacturing nitrogen-ontaining porous carbonaceous material |
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US5281319A (en) * | 1991-07-09 | 1994-01-25 | Agency Of Industrial Science And Technology | Carbon micro-sensor electrode and method for preparing it |
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JP2993343B2 (en) * | 1993-12-28 | 1999-12-20 | 日本電気株式会社 | Polarizing electrode and method of manufacturing the same |
US5536562A (en) * | 1994-03-14 | 1996-07-16 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Low-density resin impregnated ceramic article having an average density of 0.15 to 0.40 g/cc |
JPH07335501A (en) * | 1994-06-06 | 1995-12-22 | Mitsubishi Chem Corp | Carbonaceous porous body and electric double layer capacitor electrode using carbonaceous porous body |
JP3492046B2 (en) * | 1995-09-21 | 2004-02-03 | 東海カーボン株式会社 | Target material for forming antireflection film and pattern forming method |
US6350520B1 (en) * | 1998-08-26 | 2002-02-26 | Reticle, Inc. | Consolidated amorphous carbon materials, their manufacture and use |
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US5281319A (en) * | 1991-07-09 | 1994-01-25 | Agency Of Industrial Science And Technology | Carbon micro-sensor electrode and method for preparing it |
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US8414805B2 (en) | 2004-08-16 | 2013-04-09 | Electromaterials, Inc. | Porous carbon foam composites, applications, and processes of making |
JP2009196839A (en) * | 2008-02-20 | 2009-09-03 | Toyota Central R&D Labs Inc | Method for producing porous carbon article and electricity storage device |
US9000449B2 (en) | 2009-09-07 | 2015-04-07 | The University Of Tokyo | Semiconductor substrate, method for producing semiconductor substrate, substrate for semiconductor growth, method for producing substrate for semiconductor growth, semiconductor element, light-emitting element, display panel, electronic element, solar cell element, and electronic device |
CN114634229A (en) * | 2022-04-07 | 2022-06-17 | 湖南工学院 | Adsorption electrode material with porous microsphere morphology and preparation method and application thereof |
CN114634229B (en) * | 2022-04-07 | 2023-08-18 | 湖南工学院 | Adsorption electrode material with porous microsphere morphology and preparation method and application thereof |
CN115448747A (en) * | 2022-08-30 | 2022-12-09 | 易高环保能源科技(张家港)有限公司 | Graphite fiber composite foam carbon and preparation method thereof |
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EP1789364A4 (en) | 2011-04-13 |
EP1789364A1 (en) | 2007-05-30 |
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