JP4266752B2 - カーボンナノチューブ含有組成物及びその調製方法、またそれを用いた複合体及びその製造方法 - Google Patents
カーボンナノチューブ含有組成物及びその調製方法、またそれを用いた複合体及びその製造方法 Download PDFInfo
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- JP4266752B2 JP4266752B2 JP2003311926A JP2003311926A JP4266752B2 JP 4266752 B2 JP4266752 B2 JP 4266752B2 JP 2003311926 A JP2003311926 A JP 2003311926A JP 2003311926 A JP2003311926 A JP 2003311926A JP 4266752 B2 JP4266752 B2 JP 4266752B2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 123
- 239000002041 carbon nanotube Substances 0.000 title claims description 118
- 229910021393 carbon nanotube Inorganic materials 0.000 title claims description 118
- 239000000203 mixture Substances 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000002131 composite material Substances 0.000 title claims description 11
- -1 dicyanovinyl group Chemical group 0.000 claims description 136
- 239000013638 trimer Substances 0.000 claims description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 71
- 239000002904 solvent Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000003863 ammonium salts Chemical class 0.000 claims description 32
- 150000007514 bases Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 150000001450 anions Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000010409 thin film Substances 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 10
- 125000003172 aldehyde group Chemical group 0.000 claims description 10
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 10
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 9
- 239000008119 colloidal silica Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 229940085991 phosphate ion Drugs 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- CAWWUKJZAJQJIU-UHFFFAOYSA-N 2-(2-triethoxysilylethoxy)ethanol Chemical compound CCO[Si](OCC)(OCC)CCOCCO CAWWUKJZAJQJIU-UHFFFAOYSA-N 0.000 claims description 2
- RKBBVTOGABTTHK-UHFFFAOYSA-N 2-[dimethoxy(methyl)silyl]ethanethiol Chemical compound CO[Si](C)(OC)CCS RKBBVTOGABTTHK-UHFFFAOYSA-N 0.000 claims description 2
- QHQNYHZHLAAHRW-UHFFFAOYSA-N 2-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)CCN QHQNYHZHLAAHRW-UHFFFAOYSA-N 0.000 claims description 2
- ZRYKZYPYTRLNPF-UHFFFAOYSA-N 3-(3-trimethoxysilylpropoxy)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCOCCCN ZRYKZYPYTRLNPF-UHFFFAOYSA-N 0.000 claims description 2
- YATIYDNBFHEOFA-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-ol Chemical compound CO[Si](OC)(OC)CCCO YATIYDNBFHEOFA-UHFFFAOYSA-N 0.000 claims description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 description 88
- 125000005605 benzo group Chemical group 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- 150000002475 indoles Chemical class 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 22
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical class C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 19
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 150000001907 coumarones Chemical class 0.000 description 16
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229930192474 thiophene Natural products 0.000 description 15
- WDKYOIMDQCVVST-UHFFFAOYSA-N 1-benzotellurophene Chemical compound C1=CC=C2[Te]C=CC2=C1 WDKYOIMDQCVVST-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 8
- 239000002109 single walled nanotube Substances 0.000 description 8
- LCSFMUUKLRKBGA-UHFFFAOYSA-N 1h-indole-5-sulfonic acid Chemical group OS(=O)(=O)C1=CC=C2NC=CC2=C1 LCSFMUUKLRKBGA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
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- YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 6
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 229940032296 ferric chloride Drugs 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 229920000297 Rayon Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 229960003237 betaine Drugs 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
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- 230000001590 oxidative effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- 238000012546 transfer Methods 0.000 description 4
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- ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methylindole Chemical class CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 150000001408 amides Chemical class 0.000 description 3
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- 239000004917 carbon fiber Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
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- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
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- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
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- 239000004332 silver Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Description
しかしながら、カーボンナノチューブは、絡まった状態で製造されるため取扱いが非常に煩雑になるという問題がある。更に樹脂や溶液に混合した場合は、カーボンナノチューブは凝集し、カーボンナノチューブ本来の特性が発揮できないという問題もある。
この為、カーボンナノチューブに物理的処理や化学的に修飾して溶媒や樹脂に均一に分散又は溶解する試みがなされている。例えば、単層カーボンナノチューブを強酸中で超音波処理することにより単層カーボンナノチューブを短く切断して分散する方法が提案されている(非特許文献2)。
しかしながら強酸中で処理を実施するため、操作が煩雑となり、工業的には適した方法ではなく、その分散化の効果も十分とはいえない。
そこで、上記提案のように、切断された単層カーボンナノチューブは、その両末端が開いており、カルボン酸等の含酸素官能基で終端されていることに着目し、カルボン酸を酸塩化物にした後、アミン化合物と反応させて長鎖アルキル基を導入し、溶媒に可溶化することが提案されている(非特許文献3)。
しかし、本方法では単層カーボンナノチューブに共有結合して長鎖アルキル基を導入しているため、カーボンナノチューブのグラフェンシート構造の損傷やカーボンナノチューブ自体の特性に影響を与えるなどの問題点が残されている。
一方、ピレン分子は、強い相互作用によってカーボンナノチューブ表面上に吸着することが知られている。このことからピレンにアンモニウムイオンを含有する置換基を導入した化合物を単層カーボンナノチューブと水中で超音波処理を施し、非共有結合的に吸着させることにより水溶性の単層カーボンナノチューブの製造方法が報告されている(非特許文献4)。
しかしこの方法では、非共有結合型の化学修飾のためグラフェンシートの損傷などは抑制されるが、非導電性のピレン化合物が存在するため、カーボンナノチューブの導電性能が低下するという課題がある。
S. Iijima, Nature, 354,56(1991) R. E. Smalley等, Science, 280,1253(1998) J. Chen等, Science, 282,95(1998) Nakajima等, Chem.Lett., 638(2002)
Htは、NR54、S、O、Se及びTeよりなる群から選ばれたヘテロ原子基である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。)
Htは、NR54、S、O、Se及びTeよりなる群から選ばれたヘテロ原子基である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンであり、aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。)
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも1種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。)
Htは、NR54、S、O、Se及びTeよりなる群から選ばれたヘテロ原子基である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。)
Htは、NR54、S、O、Se及びTeよりなる群から選ばれたヘテロ原子基、R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。)
このなかで複素環式化合物としては、インドール誘導体類が好ましく用いられる。
本発明では、この複素環式化合物三量体を含有することにより、導電性、成膜性、成形性が向上する。
本発明に用いられる高分子化合物(d)としては、本発明に用いる溶媒(b)に溶解または分散(エマルション形成)可能であれば特に限定されるものではないが、具体的にはポリビニルアルコール、ポリビニルホルマール、ポリビニルブチラールなどのポリビニルアルコール類、ポリアクリルアマイド、ポリ(N−t−ブチルアクリルアマイド)、ポリアクリルアマイドメチルプロパンスルホン酸などのポリアクリルアマイド類、ポリビニルピロリドン類、ポリスチレンスルホン酸及びそのソーダ塩類、セルロース、アルキド樹脂、メラミン樹脂、尿素樹脂、フェノール樹脂、エポキシ樹脂、ポリブタジエン樹脂、アクリル樹脂、ウレタン樹脂、ビニルエステル樹脂、ユリア樹脂、ポリイミド樹脂、マレイン酸樹脂、ポリカーボネート樹脂、酢酸ビニル樹脂、塩素化ポリエチレン樹脂、塩素化ポリプロピレン樹脂、スチレン樹脂、アクリル/スチレン共重合樹脂、酢酸ビニル/アクリル共重合樹脂、ポリエステル樹脂、スチレン/マレイン酸共重合樹脂、フッ素樹脂及びこれらの共重合体などが用いられる。またこれらの高分子化合物(d)は2種以上を任意の割合で混合したものであってもよい。
塩基性化合物(e)としては、特に限定されるものではないが、例えば、アンモニア、脂式アミン類、環式飽和アミン類、環式不飽和アミン類やアンモニウム塩類、無機塩基などが好ましく用いられる。
界面活性剤(f)の具体例としては、アルキルスルホン酸、アルキルベンゼンスルホン酸、アルキルカルボン酸、アルキルナフタレンスルホン酸、α−オレフィンスルホン酸、ジアルキルスルホコハク酸、α−スルホン化脂肪酸、N−メチル−N−オレイルタウリン、石油スルホン酸、アルキル硫酸、硫酸化油脂、ポリオキシエチレンアルキルエーテル硫酸、ポリオキシエチレンスチレン化フェニルエーテル硫酸、アルキルリン酸、ポリオキシエチレンアルキルエーテルリン酸、ポリオキシエチレンアルキルフェニルエーテルリン酸、ナフタレンスルホン酸ホルムアルデヒド縮合物およびこれらの塩などのアニオン系界面活性剤、第一〜第三脂肪アミン、四級アンモニウム、テトラアルキルアンモニウム、トリアルキルベンジルアンモニウムアルキルピリジニウム、2−アルキル−1−アルキル−1−ヒドロキシエチルイミダゾリニウム、N,N−ジアルキルモルホリニウム、ポリエチレンポリアミン脂肪酸アミド、ポリエチレンポリアミン脂肪酸アミドの尿素縮合物、ポリエチレンポリアミン脂肪酸アミドの尿素縮合物の第四級アンモニウムおよびこれらの塩などのカチオン系界面活性剤、N,N−ジメチル−N−アルキル−N−カルボキシメチルアンモニウムベタイン、N,N,N−トリアルキル−N−スルホアルキレンアンモニウムベタイン、N,N−ジアルキル−N,N−ビスポリオキシエチレンアンモニウム硫酸エステルベタイン、2−アルキル−1−カルボキシメチル−1−ヒドロキシエチルイミダゾリニウムベタインなどのベタイン類、N,N−ジアルキルアミノアルキレンカルボン酸塩などのアミノカルボン酸類などの両性界面活性剤、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンポリスチリルフェニルエーテル、ポリオキシエチレン−ポリオキシプロピレングリコール、ポリオキシエチレン−ポリオキシプロピレンアルキルエーテル、多価アルコール脂肪酸部分エステル、ポリオキシエチレン多価アルコール脂肪酸部分エステル、ポリオキシエチレン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ポリオキシエチレン化ヒマシ油、脂肪酸ジエタノールアミド、ポリオキシエチレンアルキルアミン、トリエタノールアミン脂肪酸部分エステル、トリアルキルアミンオキサイドなどの非イオン系界面活性剤およびフルオロアルキルカルボン酸、パーフルオロアルキルカルボン酸、パーフルオロアルキルベンゼンスルホン酸、パーフルオロアルキルポリオキシエチレンエタノールなどのフッ素系界面活性剤が用いられる。ここで、アルキル基は炭素数1〜24が好ましく、炭素数3〜18がより好ましい。なお、界面活性剤は二種以上用いても何らさしつかえない。
本発明に用いられるコロイダルシリカ(h)は、特に限定されないが、水、有機溶剤または水と有機溶剤との混合溶媒に分散されているものが好ましく用いられる。有機溶剤としては、特に限定されないが例えば、メタノール、エタノール、イソプロピルアルコール、プロピルアルコール、ブタノール、ペンタノール等のアルコール類、アセトン、メチルエチルケトン、エチルイソブチルケトン、メチルイソブチルケトン等のケトン類、エチレングリコール、エチレングリコールメチルエーテル、エチレングリコールモノ−n−プロピルエーテル等のエチレングリコール類、プロピレングリコール、プロピレングリコールメチルエーテル、プロピレングリコールエチルエーテル、プロピレングリコールブチルエーテル、プロピレングリコールプロピルエーテル等のプロピレングリコール類等が好ましく用いられる。
加熱処理温度は、20℃以上、250℃以下、特に40℃〜200℃の加熱が好ましい。250℃より高いと複素環式化合物三量体(a)自体が分解してしまい導電性が著しく低下することがある。
200mlの三ツ口フラスコにアセトニトリル10mlを入れ、インドール−5−カルボン酸1.42gを溶解した。一方、酸化剤溶液の調製はアセトニトリル40mlに対して、無水塩化第二鉄16.2g、水5.4gを溶解して10分間攪拌した。次に、インドール−5−カルボン酸水溶液に30分間かけて、調製した酸化剤溶液を滴下した後、60℃で10時間攪拌した。反応溶液は若干の発熱を伴いながら薄黄色から淡緑色に変化し、そのpHは1以下であった。反応終了後、桐山漏斗で吸引濾過し、アセトニトリル次いでメタノールで洗浄し、乾燥して、淡緑色の6,11−ジヒドロ−5H−ジインドロ[2,3−a:2’,3’−c]カルバゾール−2,9,14−トリカルボン酸、(インドール−5−カルボン酸三量体)1.12g(収率79%)を得た。
得られた三量体を錠剤成型器で加圧成型させて直径10mm、厚さ1mmの形状に切り出して四端子法にて導電率を測定したところ、0.41S/cmであった。元素分析の結果は(C9.00H4.90N1.09O1.98Cl0.11)3であった。また、X線回折結晶解析の結果、層間隔は0.48nmであった。
合成例1においてインドール−5−カルボン酸の代わりにインドール−5−スルホン酸を使用する以外は合成例1と同様な方法で重合を行った。緑色の6,11−ジヒドロ−5H−ジインドロ[2,3−a:2’,3’−c]カルバゾール−2,9,14−トリスルホン酸、(インドール−5−スルホン酸三量体)1.01g(収率71%)を得た。
得られた三量体を錠剤成型器で加圧成型させて直径10mm、厚さ1mmの形状に切り出して四端子法にて導電率を測定したところ、0.56S/cmであった。元素分析の結果は(C8.00H4.85N1.06O3.01S1.06Cl0.11)3であった。
合成例1においてインドール−5−カルボン酸の代わりにインドール−5−カルボニトリルを使用する以外は合成例1と同様な方法で重合を行った。緑色の6,11−ジヒドロ−5H−ジインドロ[2,3−a:2’,3’−c]カルバゾール−2,9,14−トリカルボニトリル、(インドール−5−カルボニトリル三量体)1.22g(収率86%)を得た。
得られた三量体を錠剤成型器で加圧成型させて直径10mm、厚さ1mmの形状に切り出して四端子法にて導電率を測定したところ、0.50S/cmであった。元素分析の結果は(C9.00H4.03N1.97Cl0.10)3であった。また、X線回折結晶解析の結果、層間隔は0.44nmであった。
合成例1にて合成したインドール−5−カルボン酸三量体1.00gを、1Mアンモニア水50ml中に溶解させ、1時間攪拌した。攪拌後、アセトニトリル500mlに再沈殿させて、得られた沈殿物を桐山漏斗で吸引濾過し、水、次いでアセトニトリルで洗浄し、乾燥して、黒色の酸化型インドール−5−カルボン酸三量体0.92gを得た。元素分析の結果は(C9.00H4.34N1.07O1.99)3であった。
300mlの三ツ口フラスコにオキシンドール50.0gを、オキシ塩化リン100mlを溶媒として、空気中100℃、10時間攪拌した。反応液を氷水にゆっくり注ぎ込み過剰のオキシ塩化リンをつぶした後、水酸化ナトリウム水溶液で中和した。この溶液からクロロホルムで目的の化合物を抽出し、硫酸マグネシウムで乾燥した。ろ液から溶媒を留去し、カラムクロマトグラフィーで精製し、インドール三量体(対称型)32.5gを得た。
上記合成例1のインドール−5−カルボン酸三量体5質量部、カーボンナノチューブ(ILJIN社製 CVD法により製造された多層カーボンナノチューブ)0.4質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例1のインドール−5−カルボン酸三量体3質量部、カーボンナノチューブ0.1質量部、水系エマルジョンであるアクリル樹脂「ダイヤナールMX−1845」(三菱レイヨン社製)20質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例2のインドール−5−スルホン酸三量体3質量部、カーボンナノチューブ0.1質量部、アンモニア1質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例2のインドール−5−スルホン酸三量体3質量部、カーボンナノチューブ0.2質量部、トリエチルアミン1質量部、水系エマルジョンであるアクリル樹脂「ダイヤナールMX−1845」(三菱レイヨン社製)20質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例3のインドール−5−カルボニトリル三量体1質量部、カーボンナノチューブ0.4質量部、ドデシルベンゼンスルホン酸0.5質量部を、ジメチルスルオキシド100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例4のインドール−5−カルボン酸三量体酸化体3質量部、カーボンナノチューブ0.4質量部、γ−グリシドキシプロピルトリメトキシシラン0.5質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例5の対称型インドール三量体3質量部、カーボンナノチューブ0.4質量部、水系エマルジョンであるアクリル樹脂「ダイヤナールMX−1845」(三菱レイヨン社製)10質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
カーボンナノチューブ0.1質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
カーボンナノチューブ0.1質量部、アンモニア1質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
カーボンナノチューブ0.1質量部、水系エマルジョンであるアクリル樹脂「ダイヤナールMX−1845」(三菱レイヨン社製)20質量部を水100質量部に室温にて混合してカーボンナノチューブ含有組成物を調製した。
上記合成例3のインドール−5−カルボニトリル三量体1質量部、ドデシルベンゼンスルホン酸0.5質量部をジメチルスルオキシド100質量部に室温にて混合して導電性組成物を調製した。
また、上記各組成物において、超音波処理(神明台工(株)社製、UA100、36KHz)を1時間実施したものについて、同様に、その溶液状態を目視で観察した後、該組成物をガラス基板にバーコーター法(バーコートNo.5使用)により塗布し、80℃で5分間乾燥させ、薄膜を形成し、外観観察後、表面抵抗値を測定した。
各組成物の調製後、24時間経過した溶液状態を目視により観察した。
○:均一に分散あるいは溶解
×:不均一に分散
・表面抵抗値
25℃、15%RHの条件下で表面抵抗値を測定した。表面抵抗値が108Ω以上の場合は二探針法(電極間距離:20mm)を用い、表面抵抗値が107Ω以下の場合は四探針法(各電極間距離:5mm)を用いた。
・塗膜面外観
目視により塗膜の状態を観察した。
○:均一な塗膜が形成された。
×:カーボンナノチューブが不均一に存在する塗膜が観察された。
他方、比較例1〜3のカーボンナノチューブ含有組成物では溶液状態、表面抵抗値、塗膜面外観のいずれも劣っている。導電性組成物1を用いた比較例4は導電性が十分ではなかった。
また、本発明の複合体は、半導体、電器電子部品などの工業用包装材料、オーバーヘッドプロジェクタ用フィルム、スライドフィルムなどの電子写真記録材料等の帯電防止フィルム、オーディオテープ、ビデオテープ、コンピュータ用テープ、フレキシブルディスクなどの磁気記録媒体の帯電防止、電子デバイスのLSI配線、フィールド・エミッション・ディスプレイ(FED)の電子銃(源)及び電極、水素貯蔵剤、更に透明タッチパネル、エレクトロルミネッセンスディスプレイ、液晶ディスプレイなどの入力及び表示デバイス表面の帯電防止や透明電極、有機エレクトロルミネッセンス素子を形成する発光材料、バッファ材料、電子輸送材料、正孔輸送材料及び蛍光材料、熱転写シート、転写シート、熱転写受像シート、受像シートとして利用される。
Claims (14)
- 複素環式化合物三量体(a)、溶媒(b)、カーボンナノチューブ(c)および塩基性化合物(e)を含み、
溶媒(b)100質量部に対して、前記複素環式化合物三量体(a)が0.001〜50質量部、前記カーボンナノチューブ(c)が0.0001〜20質量部、前記塩基性化合物(e)が0.1〜10質量部であり、
前記複素環式化合物三量体(a)が下記一般式(2)で示される複素環式化合物三量体であることを特徴とするカーボンナノチューブ含有組成物。
Htは、NR54 である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。) - 複素環式化合物三量体(a)、溶媒(b)、カーボンナノチューブ(c)および塩基性化合物(e)を含み、
溶媒(b)100質量部に対して、前記複素環式化合物三量体(a)が0.001〜50質量部、前記カーボンナノチューブ(c)が0.0001〜20質量部、前記塩基性化合物(e)が0.1〜10質量部であり、
複素環式化合物三量体(a)が下記一般式(3)で示される複素環式化合物三量体であることを特徴とするカーボンナノチューブ含有組成物。
Htは、NR54 である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンであり、aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。) - 複素環式化合物三量体(a)、溶媒(b)、カーボンナノチューブ(c)および塩基性化合物(e)を含み、
溶媒(b)100質量部に対して、前記複素環式化合物三量体(a)が0.001〜50質量部、前記カーボンナノチューブ(c)が0.0001〜20質量部、前記塩基性化合物(e)が0.1〜10質量部であり、
複素環式化合物三量体(a)が下記一般式(4)で示される複素環式化合物三量体であることを特徴とするカーボンナノチューブ含有組成物。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも1種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。) - 複素環式化合物三量体(a)、溶媒(b)、カーボンナノチューブ(c)および塩基性化合物(e)を含み、
溶媒(b)100質量部に対して、前記複素環式化合物三量体(a)が0.001〜50質量部、前記カーボンナノチューブ(c)が0.0001〜20質量部、前記塩基性化合物(e)が0.1〜10質量部であり、
複素環式化合物三量体(a)が下記一般式(5)で示される複素環式化合物三量体であることを特徴とするカーボンナノチューブ含有組成物。
Htは、NR54 である。R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。
Xa-は、塩素イオン、臭素イオン、ヨウ素イオン、フッ素イオン、硝酸イオン、硫酸イオン、硫酸水素イオン、リン酸イオン、ホウフッ化イオン、過塩素酸イオン、チオシアン酸イオン、酢酸イオン、プロピオン酸イオン、メタンスルホン酸イオン、p−トルエンスルホン酸イオン、トリフルオロ酢酸イオン、及びトリフルオロメタンスルホン酸イオンよりなる1〜3価の陰イオン群より選ばれた少なくとも一種の陰イオンである。aはXのイオン価数を表し、1〜3の整数である。mはドープ率であり、その値は0〜3.0である。) - 前記複素環式化合物三量体(a)が、下記一般式(6)で示される少なくとも一種の複素環式化合物を、少なくとも一種の酸化剤と少なくとも一種の溶媒を含む反応混合物中において反応させることにより得られた複素環式化合物三量体であることを特徴とする請求項1〜4のいずれか1項に記載のカーボンナノチューブ含有組成物。
Htは、NR54 、R54は水素及び炭素数1〜24の直鎖または分岐のアルキル基よりなる群から選ばれた置換基である。) - 高分子化合物(d)を溶媒(b)100質量部に対して0.1〜400質量部含むことを特徴とする請求項1〜5のいずれかに記載のカーボンナノチューブ含有組成物。
- 界面活性剤(f)を溶媒(b)100質量部に対して0.0001〜10質量部含むことを特徴とする請求項1〜6のいずれかに記載のカーボンナノチューブ含有組成物。
- γ−グリシジルオキシプロピルトリメトキシシラン、γ−グリシジルオキシプロピルメチルジメトキシシラン、γ−グリシジルオキシプロピルトリエトキシシラン、γ−アミノプロピルトリエトキシシラン、β−アミノエチルトリメトキシシラン、γ−アミノプロポキシプロピルトリメトキシシラン、γ−メルカプトプロピルトリメトキシシラン、β−メルカプトエチルメチルジメトキシシラン、β−ヒドロキシエトキシエチルトリエトキシシラン、γ−ヒドロキシプロピルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランの群から選択されるシランカップリング剤(g)を溶媒(b)100質量部に対して0.001〜20質量部含むことを特徴とする請求項1〜7のいずれか1項に記載のカーボンナノチューブ含有組成物。
- コロイダルシリカ(h)を溶媒(b)100質量部に対して0.001〜100質量部含むことを特徴とする請求項1〜8のいずれか1項に記載のカーボンナノチューブ含有組成物。
- 前記複素環式化合物三量体が、積層構造を有することを特徴とする請求項1〜9のいずれか1項に記載のカーボンナノチューブ含有組成物。
- 請求項1〜10のいずれか1項に記載のカーボンナノチューブ含有組成物に超音波を照射して混合する処理を施すことを特徴とするカーボンナノチューブ含有組成物の調製方法。
- 基材と、その少なくとも一つの面上に形成された、請求項1〜10のいずれか1項に記載のカーボンナノチューブ含有組成物からなる薄膜とを有することを特徴とする複合体。
- 基材の少なくとも一つの面上に、請求項1〜10のいずれか1項に記載のカーボンナノチューブ含有組成物を塗布し薄膜を形成した後に、常温で放置あるいは加熱処理を行うことを特徴とする複合体の製造方法。
- 加熱処理を常温から250℃の温度範囲で行うことを特徴とする請求項13記載の複合体の製造方法。
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WO2005052053A1 (ja) * | 2003-11-27 | 2005-06-09 | National Institute Of Advanced Industrial Science And Technology | カーボンナノチューブ分散極性有機溶媒及びその製造方法 |
WO2005068556A1 (ja) * | 2004-01-20 | 2005-07-28 | National Institute Of Advanced Industrial Science And Technology | カーボンナノチューブ分散ポリイミド組成物 |
JP4575044B2 (ja) * | 2004-06-23 | 2010-11-04 | タキロン株式会社 | 音波・電波吸収体 |
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JP4824971B2 (ja) * | 2004-09-09 | 2011-11-30 | 三菱レイヨン株式会社 | ナノ物質含有組成物、その製造方法及びそれを用いた複合体 |
CN101001912B (zh) | 2004-09-09 | 2010-11-17 | 三菱丽阳株式会社 | 含纳米物质组合物、其制造方法以及使用该组合物的复合体 |
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JP6184056B2 (ja) * | 2012-04-09 | 2017-08-23 | リケンテクノス株式会社 | 樹脂組成物 |
CN103232610B (zh) * | 2013-05-14 | 2015-01-21 | 哈尔滨工业大学 | 一种定向排列自组装碳纳米管/热塑性树脂薄膜的制备方法 |
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