JP2008238162A - カーボンナノチューブ用分散剤およびこれを含むカーボンナノチューブ組成物 - Google Patents
カーボンナノチューブ用分散剤およびこれを含むカーボンナノチューブ組成物 Download PDFInfo
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- JP2008238162A JP2008238162A JP2008044773A JP2008044773A JP2008238162A JP 2008238162 A JP2008238162 A JP 2008238162A JP 2008044773 A JP2008044773 A JP 2008044773A JP 2008044773 A JP2008044773 A JP 2008044773A JP 2008238162 A JP2008238162 A JP 2008238162A
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 137
- 239000002041 carbon nanotube Substances 0.000 title claims abstract description 137
- 229910021393 carbon nanotube Inorganic materials 0.000 title claims abstract description 135
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 132
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000002612 dispersion medium Substances 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 12
- -1 polypropylene carbonate Polymers 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
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- 238000003860 storage Methods 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- HBNHCGDYYBMKJN-UHFFFAOYSA-N 2-(4-methylcyclohexyl)propan-2-yl acetate Chemical compound CC1CCC(C(C)(C)OC(C)=O)CC1 HBNHCGDYYBMKJN-UHFFFAOYSA-N 0.000 claims description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002109 single walled nanotube Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- FEIQOMCWGDNMHM-UHFFFAOYSA-N 5-phenylpenta-2,4-dienoic acid Chemical compound OC(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000002079 double walled nanotube Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 2
- 239000002048 multi walled nanotube Substances 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920000379 polypropylene carbonate Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims 2
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 claims 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 claims 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims 1
- 229920003174 cellulose-based polymer Polymers 0.000 claims 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229940116411 terpineol Drugs 0.000 claims 1
- 239000006185 dispersion Substances 0.000 abstract description 41
- 230000000694 effects Effects 0.000 abstract description 17
- 230000005684 electric field Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 238000002835 absorbance Methods 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 125000005597 hydrazone group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
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- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
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- NSYFIAVPXHGRSH-UHFFFAOYSA-N 2,5-dibromo-3-hexylthiophene Chemical compound CCCCCCC=1C=C(Br)SC=1Br NSYFIAVPXHGRSH-UHFFFAOYSA-N 0.000 description 1
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000005622 butynylene group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910021386 carbon form Inorganic materials 0.000 description 1
- 238000001628 carbon nanotube synthesis method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000010891 electric arc Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
【解決手段】分散剤は、尾部が位置規則的に配列され、尾部に対する頭部の比率が1以上になるように分散剤の構造的特性を制御することで、従来の分散剤構造に比べてカーボンナノチューブを有機溶媒、水、またはこれらの混合物などの多様な種類の分散媒中で安定化させて分散させる効果に優れる。したがって、分散剤を用いると、電界放出ディスプレイ(FED)の電界放出源、カーボンナノチューブインク、および印刷可能なカーボンナノチューブなどの各種産業分野で必要なカーボンナノチューブ組成物を容易に製造することができる。
【選択図】図1
Description
lは1〜60の整数である、で表されることが好ましい。
頭部および尾部が一方向に配列する位置規則的な分散剤構造の重合を、Ni触媒下で、次のように実施した。
頭部および尾部の方向が不規則的に配列する位置不規則的な分散剤構造の重合を、FeCl3触媒下で、次のように実施した。
下記表2のような工程を通じて分散剤5を合成した。
3−ブロモチオフェン(28ml,300mmol)とNiCl2(dppp)(0.08g,1.5mmol)とをエーテル(250ml)に入れて溶解させた後、0℃で、臭化ヘキシルマグネシウム[マグネシウム(8.75g,360mmol)と臭化ヘキシル(49.5g,420mmol)とをエーテル(250ml)中で反応させたもの]を徐々に添加した。その後、常温まで昇温して還流した。反応が終わったら、塩化アンモニウムを加えてエーテルで抽出した。減圧蒸留により精製して41.0g(244mmol,81%)の化合物1を得た。
1H NMR(δ,CDCl3):7.10(d,1H)、6.88(d,1H)、6.84(s,1H)、2.58(t,2H)、1.59(m,2H)、1.26(m,8H)、0.88(m,3.7H)
第2工程:化合物2の合成
化合物1(41g,244mmol)をTHF(500ml)に入れて−20℃に冷却した後、N,N,N,N,−テトラメチル−エチレンジアミン(40.21ml,268mmol)を添加した。次いで、30分後、−78℃に冷却した後、n−BuLi(1.6M in hexane,160ml)を加え、常温まで昇温して3時間還流した。さらに、−78℃に冷却した後、2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロレイン(60ml,293mmol)を加え、次いで常温まで昇温した後、一晩放置した。次にH2OとCH2Cl2とを抽出した後、シリカゲルカラムで分離して50.3g(171mmol,70%)の化合物2を得た。
1H NMR(δ,CDCl3):7.46(s,1H)、7.20(s,1H)、2.61(t,2H)、1.59(m,2H)、1.30(m,22H)、0.88(t,4H)
工程3:化合物3の合成
化合物1と同様の方法で合成した。
化合物3(8g,48mmol)をクロロホルム(50ml)とAcOH(150ml)に溶解させた後、0℃に冷却した。その後、光を遮断してNBS(8.55g,48mmol)を少しずつ加えた。次にNa2SO3で急冷してヘキサンで抽出した。そして、再結晶法により百色の固体7.4g(30mmol,63%)を得た。
2−ブロモチオフェン(5.3g,32mmol)、化合物2(10.5g,35.5mmol)、K2CO3(10.09g,102mmol)、pd(PPh3)4(3.9g,3.4mmol)をジメトキシエタン(150ml)とH2Oに入れて還流した。その後、塩化アンモニウムを加えてクロロホルムで抽出し、減圧蒸留により精製して6.1g(24.4mmol,76%)の化合物5を得た。
1H NMR(δ,CDCl3):7.10(m,2H)、6.98(d,1H)、6.93(dd,1H)、6.73(d,1H)、2.56(t,2H)、1.59(m,2H)、1.26(m,8H)、0.88(m,4H)
工程6:分散剤5の合成
FeCl3無水物(Anhydrous FeCl3(11.7g,72mmol))をクロロホルム(150ml)に入れて0℃に冷却した。次に化合物5(6g,24mmol)をクロロホルム(20ml)に溶解させてFeCl3溶液に徐々に流し落とした。反応が終わったらメチルアルコールに注げて沈殿させ、次いで濾して得られた固体をNH4OHに入れて常温で撹拌した。固体が赤色を帯びたら、濾してメチルアルコールで数回洗浄した後、乾燥させて試料4gを得た。
第6工程で下記表2の化合物6(化合物6は化合物5と同様の方法で製造)を上記製造例3と同様の方法で合成して試料6gを得た。
(実施例1)
上記分散剤2をNMP20mlに2mg入れて溶解させた後、この溶液にシングルウォールカーボンナノチューブ2mgを添加して超音波分散機で10時間分散させた後、8000rpmで10分間遠心分離を行ってカーボンナノチューブ溶液を得た。
分散剤として上記の分散剤3を使用したことを除けば、実施例1と同様の方法でカーボンナノチューブ溶液を得た。
分散剤として上記の分散剤1を使用したことを除けば、実施例1と同様の方法でカーボンナノチューブ溶液を得た。
分散剤として上記の分散剤4を使用したことを除けば、実施例1と同様の方法でカーボンナノチューブ溶液を得た。
上記実施例および比較例に対して次のように分散効率を評価した。
上記の測定方法により評価された、分散剤の構造的特性による分散効率を図3aおよび3bに示した。
(実施例3)
分散剤として上記分散剤5を使用したことを除けば、実施例1と同様の方法でカーボンナノチューブ溶液を得た。
分散剤として上記分散剤6を使用したことを除けば、実施例1と同様の方法でカーボンナノチューブ溶液を得た。
上記実施例3〜4および比較例3〜4に対して、上記実施例1〜2および比較例1〜2と同様の方法で分散効率を評価して図4aおよび4bに示した。
Claims (19)
- 尾部および芳香族環を有する頭部からなるカーボンナノチューブ用分散剤構造において、
前記尾部は、位置規則的(regioregular)配列であることを特徴とするカーボンナノチューブ用分散剤。 - 前記芳香族環を有する頭部から伸長している尾部を含み、かつ当該尾部の先端が一定方向に指向していることを特徴とする、請求項1に記載のカーボンナノチューブ用分散剤。
- 前記尾部および前記芳香族環を有する頭部からなるカーボンナノチューブ用分散剤構造において、
前記尾部に対する前記頭部のモル比率は、1以上であることを特徴とする、請求項1または2に記載のカーボンナノチューブ用分散剤。 - 前記尾部に対する頭部のモル比率は、1〜3であることを特徴とする、請求項1〜3のいずれか1項に記載のカーボンナノチューブ用分散剤。
- 前記頭部は、下記化学式(1):
lは、1〜60の整数である、
で表され、かつ前記尾部は、下記化学式(2):
Zは、−H,−CH3,−OH、カルボキシル基、カルボン酸塩基、スルホン酸基、スルホン酸塩基、リン酸基、およびリン酸塩基からなる群より選択され、
aは、0または1であり、
mは、1〜9の整数であり、
nは、0〜9の整数である、
請求項1〜4のいずれか一項に記載のカーボンナノチューブ用分散剤。。 - 前記化学式(1)のXは、Sであることを特徴とする、請求項5に記載のカーボンナノチューブ用分散剤。
- 前記化学式(1)のlは、10〜20の整数であることを特徴とする、請求項5または6に記載のカーボンナノチューブ用分散剤。
- 前記尾部は、炭素数3〜20のポリエチレンオキサイド、または炭素数4〜20のポリプロピレンオキサイドであることを特徴とする、請求項1〜7のいずれか一項に記載のカーボンナノチューブ用分散剤。
- 請求項1〜8のいずれか一項に記載の分散剤と、
カーボンナノチューブと、
有機溶媒、水、またはこれらの混合物から選択される分散媒と、
を含むカーボンナノチューブ組成物。 - 前記組成物は、前記組成物100質量%を基準にして、
前記分散剤0.001〜10質量%と、
カーボンナノチューブ0.01〜5質量%と、
残量の分散媒と、
を含むことを特徴とする、請求項9に記載のカーボンナノチューブ組成物。 - 前記カーボンナノチューブと分散剤との混合質量比は、1:0.001〜1:10であることを特徴とする、請求項9または10に記載のカーボンナノチューブ組成物。
- カーボンナノチューブは、シングルウォールカーボンナノチューブ、ダブルウォールカーボンナノチューブ、マルチウォールカーボンナノチューブ、および束状カーボンナノチューブからなる群より選択される一種以上であることを特徴とする、請求項9〜11のいずれか一項に記載のカーボンナノチューブ組成物。
- 前記有機溶媒は、メチルアルコール、エチルアルコール、n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、sec−ブチルアルコール、t−ブチルアルコール、イソブチルアルコール、ジアセトンアルコール、アセトン、メチルエチルケトン、メチルイソブチルケトン、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコール、1,3−プロパンジオール、1,4−ブタンジオール、1,2,4−ブタントリオール、1,5−ペンタンジオール、1,2−ヘキサンジオール、1,6−ヘキサンジオール、エチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、エチルアセテート、ブトキシエトキシエチルアセテート、ブチルカルビトールアセテート(BCA)、ジヒドロテルピネオールアセテート(DHTA)、テルピネオール、2,2,4−トリメチル−1,3−ペンタンジオールモノイソブチルエステル(テキサノール)、ジクロロエテン(DCE)、および1−メチルピロリドン(NMP)からなる群より選択される少なくとも1種であることを特徴とする、請求項9〜12のいずれか一項に記載のカーボンナノチューブ組成物。
- 請求項9〜13のいずれか一項に記載の組成物は、有機バインダー、感光性モノマー、光開始剤、粘度調節剤、貯蔵安定剤、湿潤剤、酸、および塩基からなる群より選択される一種以上の添加剤をさらに含むことを特徴とする、カーボンナノチューブ組成物。
- 前記添加剤は、前記組成物100質量%を基準にして、0.1〜60質量%を含むことを特徴とする、請求項14に記載のカーボンナノチューブ組成物。
- 前記有機バインダーは、セルロース系高分子、スチレン系高分子、スチレン−アクリル酸エステル共重合体、ポリビニルブチラール、ポリビニルアルコール、およびポリプロピレンカーボネートからなる群より選択される少なくとも1種であることを特徴とする、請求項14または15に記載のカーボンナノチューブ組成物。
- 分散剤、カーボンナノチューブ、ならび有機溶媒、水、およびこれらの混合物からなる群より選択される分散媒を混合する方法において、
前記分散剤は、尾部および芳香族環を有する頭部を含み、
前記尾部は、位置規則的配列であることを特徴とする混合方法。 - 前記混合は、溶融混合または溶解混合であることを特徴とする、請求項17に記載の混合方法。
- 前記混合は、押出機で行われることを特徴とする、請求項17または18に記載の混合方法。
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JP2006248888A (ja) * | 2005-02-10 | 2006-09-21 | Toray Ind Inc | カーボンナノチューブの製造方法 |
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JP2011084604A (ja) * | 2009-10-13 | 2011-04-28 | Inoac Gijutsu Kenkyusho:Kk | 導電性ポリウレタン発泡材料 |
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US9502152B2 (en) | 2010-11-01 | 2016-11-22 | Samsung Electronics Co., Ltd. | Method of selective separation of semiconducting carbon nanotubes, dispersion of semiconducting carbon nanotubes, and electronic device including carbon nanotubes separated by using the method |
US10355216B2 (en) | 2010-11-01 | 2019-07-16 | Samsung Electronics Co., Ltd. | Method of selective separation of semiconducting carbon nanotubes, dispersion of semiconducting carbon nanotubes, and electronic device including carbon nanotubes separated by using the method |
KR101286129B1 (ko) * | 2011-02-08 | 2013-07-15 | 광주과학기술원 | 탄소나노튜브-라디칼 고분자 복합체 및 이의 제조방법 |
JP2013001851A (ja) * | 2011-06-17 | 2013-01-07 | Toyota Boshoku Corp | カーボンナノチューブ含有樹脂組成物及びその製造方法 |
JP2014176844A (ja) * | 2013-02-15 | 2014-09-25 | Kobe Univ | 反応性界面活性剤 |
Also Published As
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US20110003907A1 (en) | 2011-01-06 |
JP5694634B2 (ja) | 2015-04-01 |
KR100847987B1 (ko) | 2008-07-22 |
US8349903B2 (en) | 2013-01-08 |
CN101310845A (zh) | 2008-11-26 |
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