JP4748761B2 - Conductivity imparting agent and conductive resin composition - Google Patents
Conductivity imparting agent and conductive resin composition Download PDFInfo
- Publication number
- JP4748761B2 JP4748761B2 JP2004216881A JP2004216881A JP4748761B2 JP 4748761 B2 JP4748761 B2 JP 4748761B2 JP 2004216881 A JP2004216881 A JP 2004216881A JP 2004216881 A JP2004216881 A JP 2004216881A JP 4748761 B2 JP4748761 B2 JP 4748761B2
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- JP
- Japan
- Prior art keywords
- cation
- parts
- resin
- conductivity
- conductive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000011342 resin composition Substances 0.000 title claims description 19
- -1 polyethylene Chemical group 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 229920005992 thermoplastic resin Polymers 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 239000004698 Polyethylene Chemical group 0.000 claims description 5
- 229920000573 polyethylene Chemical group 0.000 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000578 graft copolymer Polymers 0.000 claims description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 4
- 239000004645 polyester resin Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 229920006122 polyamide resin Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 229920005749 polyurethane resin Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000006258 conductive agent Substances 0.000 description 34
- 239000005060 rubber Substances 0.000 description 32
- 229920001971 elastomer Polymers 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000740 bleeding effect Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
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- 229920002725 thermoplastic elastomer Polymers 0.000 description 6
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 5
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 238000004898 kneading Methods 0.000 description 4
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PWZSCBSKFVJMJH-UHFFFAOYSA-N 1,1-diethylpyrrolidin-1-ium Chemical compound CC[N+]1(CC)CCCC1 PWZSCBSKFVJMJH-UHFFFAOYSA-N 0.000 description 2
- PRSAQEJPKUAHHS-UHFFFAOYSA-N 1,2-diethyl-3-methylimidazol-3-ium Chemical compound CCC=1N(C)C=C[N+]=1CC PRSAQEJPKUAHHS-UHFFFAOYSA-N 0.000 description 2
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-UHFFFAOYSA-N 0.000 description 2
- LIKOJUCTJZSUTC-UHFFFAOYSA-N 1-ethyl-2,3-dimethylpyrazol-1-ium Chemical compound C(C)[N+]=1N(C(=CC=1)C)C LIKOJUCTJZSUTC-UHFFFAOYSA-N 0.000 description 2
- OLRSYSUCJIKFOL-UHFFFAOYSA-N 1-hexyl-2-methylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=CC=C1C OLRSYSUCJIKFOL-UHFFFAOYSA-N 0.000 description 2
- OXFHNKYFIVWAAT-UHFFFAOYSA-N 2-ethyl-1,3-dimethylimidazol-1-ium Chemical compound CCC=1N(C)C=C[N+]=1C OXFHNKYFIVWAAT-UHFFFAOYSA-N 0.000 description 2
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920006311 Urethane elastomer Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000010068 moulding (rubber) Methods 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- ZECATSAUWNAQPX-UHFFFAOYSA-N 1,1-bis(2-ethoxyethyl)pyrrolidin-1-ium Chemical compound CCOCC[N+]1(CCOCC)CCCC1 ZECATSAUWNAQPX-UHFFFAOYSA-N 0.000 description 1
- LOJMDMAHMOKNHG-UHFFFAOYSA-N 1,1-bis(2-methoxyethyl)piperidin-1-ium Chemical compound COCC[N+]1(CCOC)CCCCC1 LOJMDMAHMOKNHG-UHFFFAOYSA-N 0.000 description 1
- ROVJCKUKPZCQTC-UHFFFAOYSA-N 1,1-bis(2-methoxyethyl)pyrrolidin-1-ium Chemical compound COCC[N+]1(CCOC)CCCC1 ROVJCKUKPZCQTC-UHFFFAOYSA-N 0.000 description 1
- HNVRIVKDRYGTED-UHFFFAOYSA-N 1,1-diethylpiperidin-1-ium Chemical compound CC[N+]1(CC)CCCCC1 HNVRIVKDRYGTED-UHFFFAOYSA-N 0.000 description 1
- GARJMFRQLMUUDD-UHFFFAOYSA-N 1,1-dimethylpyrrolidin-1-ium Chemical compound C[N+]1(C)CCCC1 GARJMFRQLMUUDD-UHFFFAOYSA-N 0.000 description 1
- SDKSSNOPYQAFCI-UHFFFAOYSA-N 1,1-dipentylpiperidin-1-ium Chemical compound C(CCCC)[N+]1(CCCCC1)CCCCC SDKSSNOPYQAFCI-UHFFFAOYSA-N 0.000 description 1
- PUNOSRMSQRHNLX-UHFFFAOYSA-N 1,1-dipentylpyrrolidin-1-ium Chemical compound CCCCC[N+]1(CCCCC)CCCC1 PUNOSRMSQRHNLX-UHFFFAOYSA-N 0.000 description 1
- QWBFCFUNYGOTQP-UHFFFAOYSA-N 1,1-dipropylpiperidin-1-ium Chemical compound CCC[N+]1(CCC)CCCCC1 QWBFCFUNYGOTQP-UHFFFAOYSA-N 0.000 description 1
- DREZKWDRXQDOGO-UHFFFAOYSA-N 1,2,3,4,5-pentamethylimidazol-1-ium Chemical compound CC1=C(C)[N+](C)=C(C)N1C DREZKWDRXQDOGO-UHFFFAOYSA-N 0.000 description 1
- ZSEKFPPXDDLZRG-UHFFFAOYSA-N 1,2,3,4,5-pentamethylpyrazol-1-ium Chemical compound CC1=C(C)N(C)[N+](C)=C1C ZSEKFPPXDDLZRG-UHFFFAOYSA-N 0.000 description 1
- DNSADNILRQYBAB-UHFFFAOYSA-N 1,2,3,4-tetramethylimidazol-1-ium Chemical compound CC1=C[N+](C)=C(C)N1C DNSADNILRQYBAB-UHFFFAOYSA-N 0.000 description 1
- VCQOWEYTRFURSU-UHFFFAOYSA-N 1,2,3,4-tetramethylpyrazol-1-ium Chemical compound CC=1N([N+](=CC=1C)C)C VCQOWEYTRFURSU-UHFFFAOYSA-N 0.000 description 1
- KCUGPPHNMASOTE-UHFFFAOYSA-N 1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C KCUGPPHNMASOTE-UHFFFAOYSA-N 0.000 description 1
- DTUDMIINCAAINX-UHFFFAOYSA-N 1,2,3-trimethylpyrazol-1-ium Chemical compound CC1=CC=[N+](C)N1C DTUDMIINCAAINX-UHFFFAOYSA-N 0.000 description 1
- KBNWCDNOTZWFBD-UHFFFAOYSA-N 1,2,4-trimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C(C)=C[N+](C)=C1C KBNWCDNOTZWFBD-UHFFFAOYSA-N 0.000 description 1
- FVXVZCLJHYIBID-UHFFFAOYSA-N 1,2-diethylpyrazol-1-ium Chemical compound CCN1C=CC=[N+]1CC FVXVZCLJHYIBID-UHFFFAOYSA-N 0.000 description 1
- IFGGXMRDYJZDJE-UHFFFAOYSA-N 1,2-dimethyl-3-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C=2C=CC=CC=2)=C1C IFGGXMRDYJZDJE-UHFFFAOYSA-N 0.000 description 1
- MXLZUALXSYVAIV-UHFFFAOYSA-N 1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C MXLZUALXSYVAIV-UHFFFAOYSA-N 0.000 description 1
- QMONEVQHRIIACX-UHFFFAOYSA-N 1,2-dimethyl-3-propylpyrazol-1-ium Chemical compound CCCc1cc[n+](C)n1C QMONEVQHRIIACX-UHFFFAOYSA-N 0.000 description 1
- OOVZOSXHSAFMJZ-UHFFFAOYSA-N 1,2-dimethylindazol-2-ium Chemical compound C1=CC=CC2=[N+](C)N(C)C=C21 OOVZOSXHSAFMJZ-UHFFFAOYSA-N 0.000 description 1
- PSIOIZDELPYQPO-UHFFFAOYSA-N 1,2-dimethylpyrazol-1-ium Chemical compound CN1C=CC=[N+]1C PSIOIZDELPYQPO-UHFFFAOYSA-N 0.000 description 1
- UMZDENILBZKMFY-UHFFFAOYSA-N 1,2-dimethylpyridin-1-ium Chemical compound CC1=CC=CC=[N+]1C UMZDENILBZKMFY-UHFFFAOYSA-N 0.000 description 1
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 description 1
- WGBOEVMWOWERBH-UHFFFAOYSA-N 1,3-diethyl-2-methylimidazol-1-ium Chemical compound CCN1C=C[N+](CC)=C1C WGBOEVMWOWERBH-UHFFFAOYSA-N 0.000 description 1
- OBTFKSNFKVPPFY-UHFFFAOYSA-N 1,3-dimethyl-2-phenylimidazol-1-ium Chemical compound CN1C=C[N+](C)=C1C1=CC=CC=C1 OBTFKSNFKVPPFY-UHFFFAOYSA-N 0.000 description 1
- QLCFPHFMJGGHRV-UHFFFAOYSA-N 1,3-dimethyl-2-phenylpyrazol-1-ium Chemical compound Cc1cc[n+](C)n1-c1ccccc1 QLCFPHFMJGGHRV-UHFFFAOYSA-N 0.000 description 1
- IJDNIXNJORNVTA-UHFFFAOYSA-N 1,3-dimethyl-2-propylimidazol-1-ium Chemical compound CCCC=1N(C)C=C[N+]=1C IJDNIXNJORNVTA-UHFFFAOYSA-N 0.000 description 1
- DZEHNHDJHLMTNH-UHFFFAOYSA-N 1,3-dimethyl-2-undecylimidazol-1-ium Chemical compound CCCCCCCCCCCC=1N(C)C=C[N+]=1C DZEHNHDJHLMTNH-UHFFFAOYSA-N 0.000 description 1
- DSPUBTKMQXMJCI-UHFFFAOYSA-N 1,3-dimethylbenzimidazol-3-ium Chemical compound C1=CC=C2N(C)C=[N+](C)C2=C1 DSPUBTKMQXMJCI-UHFFFAOYSA-N 0.000 description 1
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 1
- MFBWQECTECUPHC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-(2-methoxyethyl)piperidin-1-ium Chemical compound COCC[N+]1(CCCCC1)CCOCC MFBWQECTECUPHC-UHFFFAOYSA-N 0.000 description 1
- NEXAIWPUQRUIJB-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-(2-methoxyethyl)pyrrolidin-1-ium Chemical compound COCC[N+]1(CCCC1)CCOCC NEXAIWPUQRUIJB-UHFFFAOYSA-N 0.000 description 1
- NPEHXFZXBZPYME-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-ethylpiperidin-1-ium Chemical compound CCOCC[N+]1(CC)CCCCC1 NPEHXFZXBZPYME-UHFFFAOYSA-N 0.000 description 1
- MAXRBXCATDASNL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-methylpiperidin-1-ium Chemical compound CCOCC[N+]1(C)CCCCC1 MAXRBXCATDASNL-UHFFFAOYSA-N 0.000 description 1
- HPHJLXQRQWXQGB-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-methylpyrrolidin-1-ium Chemical compound CCOCC[N+]1(C)CCCC1 HPHJLXQRQWXQGB-UHFFFAOYSA-N 0.000 description 1
- AATXQZHDRFTOAN-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-propylpiperidin-1-ium Chemical compound CCOCC[N+]1(CCC)CCCCC1 AATXQZHDRFTOAN-UHFFFAOYSA-N 0.000 description 1
- IZMCIDYAUVFQBZ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-propylpyrrolidin-1-ium Chemical compound CCOCC[N+]1(CCC)CCCC1 IZMCIDYAUVFQBZ-UHFFFAOYSA-N 0.000 description 1
- DSIZWXRKCNMRRB-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methylpiperidin-1-ium Chemical compound COCC[N+]1(C)CCCCC1 DSIZWXRKCNMRRB-UHFFFAOYSA-N 0.000 description 1
- IDTCZPKYVMKLRZ-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methylpyrrolidin-1-ium Chemical compound COCC[N+]1(C)CCCC1 IDTCZPKYVMKLRZ-UHFFFAOYSA-N 0.000 description 1
- OTLQQASHDLVKMH-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-propylpiperidin-1-ium Chemical compound COCC[N+]1(CCC)CCCCC1 OTLQQASHDLVKMH-UHFFFAOYSA-N 0.000 description 1
- LZCSZDHIDXZSGI-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-propylpyrrolidin-1-ium Chemical compound COCC[N+]1(CCC)CCCC1 LZCSZDHIDXZSGI-UHFFFAOYSA-N 0.000 description 1
- HGIKIBHZIYNEKO-UHFFFAOYSA-N 1-benzyl-2,3-dimethylimidazol-3-ium Chemical compound C1=C[N+](C)=C(C)N1CC1=CC=CC=C1 HGIKIBHZIYNEKO-UHFFFAOYSA-N 0.000 description 1
- COSSPXYCRNRXRX-UHFFFAOYSA-N 1-benzyl-3-methylimidazol-3-ium Chemical compound C1=[N+](C)C=CN1CC1=CC=CC=C1 COSSPXYCRNRXRX-UHFFFAOYSA-N 0.000 description 1
- GYZXRPOUUZKBAT-UHFFFAOYSA-N 1-butyl-2-ethylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1CC GYZXRPOUUZKBAT-UHFFFAOYSA-N 0.000 description 1
- BHIGPVGNEXDQBL-UHFFFAOYSA-N 1-butyl-2-methylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1C BHIGPVGNEXDQBL-UHFFFAOYSA-N 0.000 description 1
- UVXPACHEJJJYRU-UHFFFAOYSA-N 1-butyl-2-propylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1CCC UVXPACHEJJJYRU-UHFFFAOYSA-N 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 description 1
- AAINAVGFOSLVFN-UHFFFAOYSA-N 1-ethyl-1-(2-methoxyethyl)piperidin-1-ium Chemical compound COCC[N+]1(CC)CCCCC1 AAINAVGFOSLVFN-UHFFFAOYSA-N 0.000 description 1
- DICGWOWEOGIPCE-UHFFFAOYSA-N 1-ethyl-1-(2-methoxyethyl)pyrrolidin-1-ium Chemical compound COCC[N+]1(CC)CCCC1 DICGWOWEOGIPCE-UHFFFAOYSA-N 0.000 description 1
- WACRAFUNNYGNEQ-UHFFFAOYSA-N 1-ethyl-1-methylpiperidin-1-ium Chemical compound CC[N+]1(C)CCCCC1 WACRAFUNNYGNEQ-UHFFFAOYSA-N 0.000 description 1
- NIHOUJYFWMURBG-UHFFFAOYSA-N 1-ethyl-1-methylpyrrolidin-1-ium Chemical compound CC[N+]1(C)CCCC1 NIHOUJYFWMURBG-UHFFFAOYSA-N 0.000 description 1
- WQJAOAVHWUDVMV-UHFFFAOYSA-N 1-ethyl-1-propylpiperidin-1-ium Chemical compound CCC[N+]1(CC)CCCCC1 WQJAOAVHWUDVMV-UHFFFAOYSA-N 0.000 description 1
- QNXMTMCQDZQADU-UHFFFAOYSA-N 1-ethyl-1-propylpyrrolidin-1-ium Chemical compound CCC[N+]1(CC)CCCC1 QNXMTMCQDZQADU-UHFFFAOYSA-N 0.000 description 1
- BOFPDEISADDIGX-UHFFFAOYSA-N 1-ethyl-2-methylpyrazol-2-ium Chemical compound CCN1C=CC=[N+]1C BOFPDEISADDIGX-UHFFFAOYSA-N 0.000 description 1
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- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
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- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 description 1
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- RRYKUXCBJXYIOD-UHFFFAOYSA-N 1-methyl-1-pentylpyrrolidin-1-ium Chemical compound CCCCC[N+]1(C)CCCC1 RRYKUXCBJXYIOD-UHFFFAOYSA-N 0.000 description 1
- OGLIVJFAKNJZRE-UHFFFAOYSA-N 1-methyl-1-propylpiperidin-1-ium Chemical compound CCC[N+]1(C)CCCCC1 OGLIVJFAKNJZRE-UHFFFAOYSA-N 0.000 description 1
- ICSNGQOODNUMGE-UHFFFAOYSA-N 1-methyl-2-phenylpyrazol-1-ium Chemical compound C[N+]1=CC=CN1C1=CC=CC=C1 ICSNGQOODNUMGE-UHFFFAOYSA-N 0.000 description 1
- UGCPLZSPKGRDMW-UHFFFAOYSA-N 1-methyl-3-phenylimidazol-1-ium Chemical compound C1=[N+](C)C=CN1C1=CC=CC=C1 UGCPLZSPKGRDMW-UHFFFAOYSA-N 0.000 description 1
- XDEQOBPALZZTCA-UHFFFAOYSA-N 1-octylpyridin-1-ium Chemical compound CCCCCCCC[N+]1=CC=CC=C1 XDEQOBPALZZTCA-UHFFFAOYSA-N 0.000 description 1
- HOZSKYZXBJWURK-UHFFFAOYSA-N 1-pentylpyridin-1-ium Chemical compound CCCCC[N+]1=CC=CC=C1 HOZSKYZXBJWURK-UHFFFAOYSA-N 0.000 description 1
- CRTKBIFIDSNKCN-UHFFFAOYSA-N 1-propylpyridin-1-ium Chemical compound CCC[N+]1=CC=CC=C1 CRTKBIFIDSNKCN-UHFFFAOYSA-N 0.000 description 1
- UOSOXBWHXHMEFN-UHFFFAOYSA-N 2,3-dimethyl-1,3-oxazol-3-ium Chemical compound CC=1OC=C[N+]=1C UOSOXBWHXHMEFN-UHFFFAOYSA-N 0.000 description 1
- WTHSUBLYGFYEKU-UHFFFAOYSA-N 2,3-dimethyl-1,3-thiazol-3-ium Chemical compound CC=1SC=C[N+]=1C WTHSUBLYGFYEKU-UHFFFAOYSA-N 0.000 description 1
- DGNYAZDXTWRIJV-UHFFFAOYSA-N 2,3-dimethyl-1-phenylpyrazol-1-ium Chemical compound CN1C(C)=CC=[N+]1C1=CC=CC=C1 DGNYAZDXTWRIJV-UHFFFAOYSA-N 0.000 description 1
- GHGZGDGWFWIAQM-UHFFFAOYSA-O 2,4,5-trimethyl-1H-pyrazol-2-ium Chemical compound CC=1C=[N+](C)NC=1C GHGZGDGWFWIAQM-UHFFFAOYSA-O 0.000 description 1
- UJBYZFKDBNQRBW-UHFFFAOYSA-N 2-benzyl-1,3-dimethylimidazol-1-ium Chemical compound CN1C=C[N+](C)=C1CC1=CC=CC=C1 UJBYZFKDBNQRBW-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
Description
本発明は、熱可塑性樹脂またはゴムに導電性を付与させるための導電性付与剤及び導電性シートまたは電子写真式プリンターや複写機の導電性ロール（帯電ロール、クリーニングロール、現像ロールなど）に用いられる導電性樹脂組成物に関する。 The present invention is used for a conductivity imparting agent for imparting conductivity to a thermoplastic resin or rubber and a conductive sheet, or a conductive roll (electrostatic roll, cleaning roll, developing roll, etc.) of an electrophotographic printer or copying machine. The present invention relates to a conductive resin composition.
電子写真式プリンターや複写機等の画像形成装置に使用される帯電ロール、転写ロール、クリーニングロール、現像ロールなどに用いられる導電性樹脂組成物は、ポリウレタン、スチレンゴム、エピクロルヒドリンゴムなどの熱可塑性樹脂またはゴムに導電性付与剤を添加して、表面抵抗を１０７〜１０9Ω／□に調整して使用される。 Conductive resin compositions used for charging rolls, transfer rolls, cleaning rolls, developing rolls, etc. used in image forming apparatuses such as electrophotographic printers and copiers are thermoplastic resins such as polyurethane, styrene rubber, epichlorohydrin rubber, etc. Alternatively, a conductivity imparting agent is added to rubber to adjust the surface resistance to 10 7 to 10 9 Ω / □.
従来、該導電性付与剤としては、カーボンブラックや金属、金属酸化物の電子導電剤が用いられているが、これらを樹脂またはゴムに添加させた場合、得られる導電性樹脂組成物は、硬度が高くなることから、軟化剤を配合させて硬度を低くする必要があった。しかしながら、時間の経過とともにブリードが発生し、該軟化剤がしみ出して他部材を汚染するという問題があった。 Conventionally, carbon black, metal, and metal oxide electronic conductive agents are used as the conductivity imparting agent. When these are added to a resin or rubber, the resulting conductive resin composition has a hardness of Therefore, it was necessary to add a softener to reduce the hardness. However, there is a problem that bleed occurs with time and the softener oozes out and contaminates other members.
また、ゴム等に電子導電剤を添加させて得られた導電性樹脂組成物は、電気抵抗のばらつきや電圧依存性が大きい等の問題があった。 Further, the conductive resin composition obtained by adding an electronic conductive agent to rubber or the like has problems such as variation in electric resistance and large voltage dependency.
上記課題を解決するために、該電子導電剤に代えて、ゴム等の柔軟性を保ちつつ、電気抵抗のばらつきや電圧依存性が小さい等の利点を有するイオン導電剤が提案されている。 In order to solve the above problems, an ionic conductive agent having advantages such as variation in electric resistance and small voltage dependence has been proposed in place of the electronic conductive agent while maintaining flexibility such as rubber.
特許文献１には、樹脂に過塩素酸リチウム等のアルカリ金属塩を添加させた導電性樹脂組成物が記載されている。 Patent Document 1 describes a conductive resin composition in which an alkali metal salt such as lithium perchlorate is added to a resin.
しかしながら、従来の過塩素酸リチウム等のアルカリ金属塩をイオン導電剤として用いた場合、長時間通電状態にすると漸次抵抗が増大し、ブリードを生じてイオン導電剤がしみ出すなどの問題があった。また、上記イオン導電剤は、ポリウレタン等の樹脂に対する相溶性に劣ることから大量に添加することが困難であり、抵抗値の調整に制限が生じる場合があった。 However, when a conventional alkali metal salt such as lithium perchlorate is used as an ionic conductive agent, there is a problem that the ionic conductive agent oozes out due to gradual increase in resistance when energized for a long time. . In addition, the ionic conductive agent is incompatible with resins such as polyurethane, so it is difficult to add a large amount thereof, and there are cases where the adjustment of the resistance value is limited.
本発明の目的は、導電性及び柔軟性が高く、ブリードによるイオン導電剤のしみ出しが低減された、長期安定性に優れた導電性付与剤及び導電性樹脂組成物を提供することにある。 An object of the present invention is to provide a conductivity-imparting agent and a conductive resin composition that are highly conductive and flexible, have reduced exudation of an ionic conductive agent due to bleeding, and have excellent long-term stability.
本発明者らは鋭意検討した結果、第４級化合物塩からなるイオン導電剤が含有されてなる導電性付与剤及び該導電性付与剤を含有させてなる導電性樹脂組成物が上記課題を解決し得ることを見出し、本発明を完成するに至った。 As a result of intensive studies, the inventors of the present invention have solved the above problems by a conductivity-imparting agent containing an ionic conductive agent comprising a quaternary compound salt and a conductive resin composition containing the conductivity-imparting agent. As a result, the present invention has been completed.
すなわち、本発明は、下記一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩からなるイオン導電剤が含有されてなることを特徴とする導電性付与剤である。 That is, the present invention is a conductivity-imparting agent comprising an ionic conductive agent comprising a cyclic perfluoroalkylene disulfonimide salt represented by the following general formula [1].
一般式中、ｎは２〜８の正整数を、Ｘ＋は第４級オニウムカチオンを表す。 In the general formula, n represents a positive integer of 2 to 8, and X + represents a quaternary onium cation.
また、本発明は一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩からなるイオン導電剤が、末端水酸基を有するポリエーテルポリオール、末端水酸基を有するポリアルキレングリコール、末端水酸基を有するポリエチレン主鎖とポリアルキレンオキサイドとのグラフト共重合体からなる群から選ばれる少なくとも１種に含有されてなることを特徴とする導電性付与剤である。 In the present invention, the ionic conductive agent comprising the cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1] is a polyether polyol having a terminal hydroxyl group, a polyalkylene glycol having a terminal hydroxyl group, and a polyethylene having a terminal hydroxyl group. It is an electroconductivity imparting agent characterized by being contained in at least one selected from the group consisting of a graft copolymer of a chain and a polyalkylene oxide.
また、本発明は、上記一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩が、熱可塑性樹脂またはゴムに添加されてなることを特徴とする導電性樹脂組成物である。 The present invention also provides a conductive resin composition comprising a cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1] added to a thermoplastic resin or rubber.
本発明の導電性付与剤は、イオン導電性の高い環状パーフルオロアルキレンジスルホンイミド塩が含有されてなり、該導電性付与剤が添加された導電性樹脂組成物は、ブリードによるイオン導電剤のしみ出しがなく、導電性、柔軟性に優れ、長期間安定した特性が発現できる。 The conductivity-imparting agent of the present invention contains a cyclic perfluoroalkylene disulfonimide salt having high ionic conductivity, and the conductive resin composition to which the conductivity-imparting agent is added is a stain of the ionic conductivity agent due to bleeding. There is no sticking out, excellent conductivity and flexibility, and stable characteristics can be expressed for a long time.
以下、本発明を実施するための最良の形態を詳細に説明する。 Hereinafter, the best mode for carrying out the present invention will be described in detail.
本発明の導電性付与剤は、イオン導電剤である上記一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩が含有されてなり、一般式〔１〕中、ｎは２〜８の正整数を、Ｘ＋は第４級オニウムカチオンを表す。ここで、ｎは好ましくは２〜６であり、より好ましくはｎが３である。 The conductivity-imparting agent of the present invention contains a cyclic perfluoroalkylene disulfonimide salt represented by the above general formula [1], which is an ionic conductive agent. In the general formula [1], n is 2 to 8. A positive integer, X + represents a quaternary onium cation. Here, n is preferably 2 to 6, and more preferably n is 3.
一般式〔１〕中、Ｘ＋は第４級オニウムカチオンを表し、例えば、アンモニウム、ピロリジニウム、ピペリジニウム、モルホニウム、ピリジニウム、イミダゾリウム、ピラゾリウム、チアゾリウム、オキサゾリウム、トリアゾリウム等のカチオン成分があげられる。 In the general formula [1], X + represents a quaternary onium cation, and examples thereof include cation components such as ammonium, pyrrolidinium, piperidinium, morphonium, pyridinium, imidazolium, pyrazolium, thiazolium, oxazolium, and triazolium.
アンモニウムカチオンとしてはテトラメチルアンモニウム、トリメチルエチルアンモニウム、トリメチルプロピルアンモニウム、ジメチルジエチルアンモニウム、ジメチルエチルプロピルアンモニウム、ジメチルジプロピルアンモニウム、メチルトリエチルアンモニウム、メチルジエチルプロピルアンモニウム、メチルエチルジプロピルアンモニウム、メチルトリプロピルアンモニウム、テトラエチルアンモニウム、トリエチルプロピルアンモニウム、ジエチルジプロピルアンモニウム、エチルトリプロピルアンモニウム、テトラプロピルアンモニウム、テトラブチルアンモニウム、テトラペンチルアンモニウム、テトラオクチルアンモニウム、メチルトリブチルアンモニウム、メチルトリペンチルアンモニウム、トリメチルメトキシエチルアンモニウム、ジメチルエチルメトキシエチルアンモニウム、ジメチルプロピルメトキシエチルアンモニウム、メチルジエチルメトキシエチルアンモニウム、メチルエチルプロピルメトキシエチルアンモニウム、メチルジプロピルメトキシエチルアンモニウム、トリエチルメトキシエチルアンモニウム、ジエチルプロピルメトキシエチルアンモニウム、エチルジプロピルメトキシエチルアンモニウム、トリプロピルメトキシエチルアンモニウムなどがあげられるが、これらに限定されるものではない。 Examples of ammonium cations include tetramethylammonium, trimethylethylammonium, trimethylpropylammonium, dimethyldiethylammonium, dimethylethylpropylammonium, dimethyldipropylammonium, methyltriethylammonium, methyldiethylpropylammonium, methylethyldipropylammonium, methyltripropylammonium, Tetraethylammonium, triethylpropylammonium, diethyldipropylammonium, ethyltripropylammonium, tetrapropylammonium, tetrabutylammonium, tetrapentylammonium, tetraoctylammonium, methyltributylammonium, methyltripentylammonium, trimethylmethoxyethyl Ammonium, dimethylethylmethoxyethylammonium, dimethylpropylmethoxyethylammonium, methyldiethylmethoxyethylammonium, methylethylpropylmethoxyethylammonium, methyldipropylmethoxyethylammonium, triethylmethoxyethylammonium, diethylpropylmethoxyethylammonium, ethyldipropylmethoxyethyl Examples thereof include, but are not limited to, ammonium and tripropylmethoxyethylammonium.
ピロリジニウムカチオンとしては、Ｎ，Ｎ−ジメチルピロリジニウム、Ｎ，Ｎ−メチルエチルピロリジニウム、Ｎ，Ｎ−メチルプロピルアンモニウム、Ｎ，Ｎ−メチルメトキシエチルピロリジニウム、Ｎ，Ｎ−メチルエトキシエチルピロリジニウム、Ｎ，Ｎ−ジエチルピロリジニウム、Ｎ，Ｎ−エチルプロピルピロリジニウム、Ｎ，Ｎ−エチルメトキシエチルピロリジニウム、Ｎ，Ｎ−エチルエトキシエチルピロリジニウムＮ，Ｎ−ジプロピルピロリジニウム、Ｎ，Ｎ−プロピルメトキシエチルピロリジニウム、Ｎ，Ｎ−プロピルエトキシエチルピロリジニウム、Ｎ，Ｎ−ジ（メトキシエチル）ピロリジニウム、Ｎ，Ｎ−ジ（エトキシエチル）ピロリジニウム、Ｎ，Ｎ−（メトキシエチル）−（エトキシエチル）ピロリジニウムＮ，Ｎ−ジブチルピロリジニウムＮ，Ｎ−ジペンチルピロリジニウムＮ，Ｎ−メチルペンチルピロリジニウムスピロ−（１，１’）−ビアザシクロブチル、アザシクロペンタン−１−スピロ−１’−アザシクロブチル、アザシクロヘキサン−１−スピロ−１’−アザシクロブチル、アザシクロヘプタン−１−スピロ−１’− アザシクロブチル、アザシクロオクタン−１−スピロ−１’− アザシクロブチルなどがあげられるが、これらに限定されるものではない。 As pyrrolidinium cations, N, N-dimethylpyrrolidinium, N, N-methylethylpyrrolidinium, N, N-methylpropylammonium, N, N-methylmethoxyethylpyrrolidinium, N, N-methyl Ethoxyethylpyrrolidinium, N, N-diethylpyrrolidinium, N, N-ethylpropylpyrrolidinium, N, N-ethylmethoxyethylpyrrolidinium, N, N-ethylethoxyethylpyrrolidinium N, N- Dipropylpyrrolidinium, N, N-propylmethoxyethylpyrrolidinium, N, N-propylethoxyethylpyrrolidinium, N, N-di (methoxyethyl) pyrrolidinium, N, N-di (ethoxyethyl) pyrrolidinium, N, N- (methoxyethyl)-(ethoxyethyl) pyrrolidinium N, N-dibu Rupyrrolidinium N, N-dipentylpyrrolidinium N, N-methylpentylpyrrolidinium spiro- (1,1 ′)-biazacyclobutyl, azacyclopentane-1-spiro-1′-azacyclobutyl, azacyclohexane 1-spiro-1′-azacyclobutyl, azacycloheptane-1-spiro-1′-azacyclobutyl, azacyclooctane-1-spiro-1′-azacyclobutyl, and the like. It is not something.
ピペリジニウムカチオンとしては、Ｎ，Ｎ−ジメチルピペリジニウム、Ｎ，Ｎ−メチルエチルピペリジニウム、Ｎ，Ｎ−メチルプロピルピペリジニウム、Ｎ，Ｎ−メチルメトキシエチルピペリジニウム、Ｎ，Ｎ−メチルエトキシエチルピペリジニウム、Ｎ，Ｎ−ジエチルピペリジニウム、Ｎ，Ｎ−エチルプロピルピペリジニウム、Ｎ，Ｎ−エチルメトキシエチルピペリジニウム、Ｎ，Ｎ−エチルエトキシエチルピペリジニウム、Ｎ，Ｎ−ジプロピルピペリジニウム、Ｎ，Ｎ−プロピルメトキシエチルピペリジニウム、Ｎ，Ｎ−プロピルエトキシエチルピペリジニウム、Ｎ，Ｎ−ジ（メトキシエチル）ピペリジニウム、Ｎ，Ｎ−ジ（エトキシエチル）ピペリジニウム、Ｎ，Ｎ−（メトキシエチル）−（エトキシエチル）ピペリジニウムＮ，Ｎ−ジブチルピペリジニウム、Ｎ，Ｎ−ジペンチルピペリジニウム、Ｎ，Ｎ−メチルペンチルピペリジニウム、スピロ−（１，１’）−ビアザシクロペンチル、アザシクロヘキサン−１−スピロ−１’−アザシクロペンチル、アザシクロヘプタン−１−スピロ−１’− アザシクロペンチル、アザシクロオクタン−１−スピロ−１’− アザシクロペンチルなどがあげられるが、これらに限定されるものではない。 As piperidinium cations, N, N-dimethylpiperidinium, N, N-methylethylpiperidinium, N, N-methylpropylpiperidinium, N, N-methylmethoxyethylpiperidinium, N, N -Methylethoxyethylpiperidinium, N, N-diethylpiperidinium, N, N-ethylpropylpiperidinium, N, N-ethylmethoxyethylpiperidinium, N, N-ethylethoxyethylpiperidinium, N , N-dipropylpiperidinium, N, N-propylmethoxyethylpiperidinium, N, N-propylethoxyethylpiperidinium, N, N-di (methoxyethyl) piperidinium, N, N-di (ethoxyethyl) ) Piperidinium, N, N- (methoxyethyl)-(ethoxyethyl) piperidinium N, N- Butylpiperidinium, N, N-dipentylpiperidinium, N, N-methylpentylpiperidinium, spiro- (1,1 ′)-biazacyclopentyl, azacyclohexane-1-spiro-1′-azacyclopentyl, Examples include, but are not limited to, azacycloheptane-1-spiro-1′-azacyclopentyl, azacyclooctane-1-spiro-1′-azacyclopentyl.
モルホニウムカチオンとしては、Ｎ，Ｎ−ジメチルモルホニウム、Ｎ，Ｎ−メチルエチルモルホニウム、Ｎ，Ｎ−メチルプロピルモルホニウム、Ｎ，Ｎ−メチルメトキシエチルモルホニウム、Ｎ，Ｎ−メチルエトキシエチルモルホニウム、Ｎ，Ｎ−ジエチルモルホニウム、Ｎ，Ｎ−エチルプロピルモルホニウム、Ｎ，Ｎ−エチルメトキシエチルモルホニウム、Ｎ，Ｎ−エチルエトキシエチルモルホニウム、Ｎ，Ｎ−ジプロピルモルホニウム、Ｎ，Ｎ−プロピルメトキシエチルモルホニウム、Ｎ，Ｎ−プロピルエトキシエチルモルホニウム、Ｎ，Ｎ−ジ（メトキシエチル）モルホニウム、Ｎ，Ｎ−ジ（エトキシエチル）モルホニウム、Ｎ，Ｎ−ジブチルモルホニウム、Ｎ，Ｎ−ジペンチルモルホニウム、Ｎ，Ｎ−メチルペンチルモルホニウム、Ｎ，Ｎ−（メトキシエチル）−（エトキシエチル）モルホニウム、モルホリン−４−スピロ−１’−アザシクロブチル、モルホリン−４−スピロ−１’−アザシクロペンチル、モルホリン−４−スピロ−１’−アザシクロヘキシル、モルホリン−４−スピロ−１’−アザシクロヘプチル、モルホリン−４−スピロ−１’−アザシクロオクチルなどがあげられるが、これらに限定されるものではない。 Examples of the morphonium cation include N, N-dimethylmorphonium, N, N-methylethylmorphonium, N, N-methylpropylmorphonium, N, N-methylmethoxyethylmorphonium, N, N. -Methylethoxyethylmorphonium, N, N-diethylmorphonium, N, N-ethylpropylmorphonium, N, N-ethylmethoxyethylmorphonium, N, N-ethylethoxyethylmorphonium, N , N-dipropylmorphonium, N, N-propylmethoxyethylmorphonium, N, N-propylethoxyethylmorphonium, N, N-di (methoxyethyl) morphonium, N, N-di (ethoxyethyl) ) Morphonium, N, N-dibutylmorphonium, N, N-dipentylmorphonium, N, N-methylpentylmorphonium, , N- (methoxyethyl)-(ethoxyethyl) morphonium, morpholine-4-spiro-1′-azacyclobutyl, morpholine-4-spiro-1′-azacyclopentyl, morpholine-4-spiro-1′-azacyclohexyl Morpholine-4-spiro-1′-azacycloheptyl, morpholine-4-spiro-1′-azacyclooctyl, and the like, but are not limited thereto.
ピリジニウムカチオンとしては、Ｎ−メチルピリジニウム、Ｎ−エチルピリジニウム、Ｎ−プロピルピリジニウム、Ｎ−ブチルピリジニウム、Ｎ−ペンチルピリジニウム、Ｎ−ヘキシルピリジニウム、Ｎ−オクチルピリジニウム、Ｎ−メチル−メチルピリジニウム、Ｎ−メチル−エチルピリジニウム、Ｎ−メチル−ブチルピリジニウム、Ｎ−エチル−メチルピリジニウム、Ｎ−ブチル−メチルピリジニウム、Ｎ−ブチルーエチルピリジニウム、Ｎ−ブチル−プロピルピリジニウム、Ｎ−ヘキシル−メチルピリジニウム、Ｎ−オクチル−メチルピリジニウムなどがあげられるが、これらに限定されるものではない。 Examples of the pyridinium cation include N-methylpyridinium, N-ethylpyridinium, N-propylpyridinium, N-butylpyridinium, N-pentylpyridinium, N-hexylpyridinium, N-octylpyridinium, N-methyl-methylpyridinium, N-methyl -Ethylpyridinium, N-methyl-butylpyridinium, N-ethyl-methylpyridinium, N-butyl-methylpyridinium, N-butyl-ethylpyridinium, N-butyl-propylpyridinium, N-hexyl-methylpyridinium, N-octyl- Examples include, but are not limited to, methylpyridinium.
イミダゾリウムカチオンとしては１，３−ジメチルイミダゾリウム、１，２，３−トリメチルイミダゾリウム、１−エチル−３−メチルイミダゾリウム、１−エチル−２，３−ジメチルイミダゾリウム、１，３−ジエチルイミダゾリウム、１，２−ジエチル−３−メチルイミダゾリウム、１，３−ジエチル−２−メチルイミダゾリウム、１，２−ジメチル−３−プロピルイミダゾリウム、１−ブチル−３−メチルイミダゾリウム、１−メチル−３−プロピル−２，４−ジメチルイミダゾリウム、１，２，３，４−テトラメチルイミダゾリウム、１，２，３，４，５−ペンタメチルイミダゾリウム、２−エチル−１，３−ジメチルイミダゾリウム、１，３−ジメチル−２−プロピルイミダゾリウム、１，３−ジメチル−２−ペンチルイミダゾリウム、１，３−ジメチル−２−ヘプチルイミダゾリウム、１，３，４−トリメチルイミダゾリウム、２−エチル−１，３，４−トリメチルイミダゾリウム、１，３−ジメチルベンゾイミダゾリウム、１−フェニル−３−メチルイミダゾリウム、１−ベンジル−３−メチルイミダゾリウム、１−フェニル−２，３−ジメチルイミダゾリウム、１−ベンジル−２，３−ジメチルイミダゾリウム、２−フェニル−１，３−ジメチルイミダゾリウム、２−ベンジル−１，３−ジメチルイミダゾリウム、１，３−ジメチル−２−ウンデシルイミダゾリウム、１，３−ジメチル−２−ヘプタデシルイミダゾリウム２−（２′−ヒドロキシ）エチル−１，３−ジメチルイミダゾリウム、１−（２′−ヒドロキシ）エチル−２，３−ジメチルイミダゾリウム、２−エトキシメチル−１，３−ジメチルイミダゾリウム、１−エトキシメチル−２，３−ジメチルイミダゾリウムがあげられるが、これらに限定されるものではない。 Examples of imidazolium cations include 1,3-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-3-methylimidazolium, 1-ethyl-2,3-dimethylimidazolium, and 1,3-diethyl. Imidazolium, 1,2-diethyl-3-methylimidazolium, 1,3-diethyl-2-methylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-butyl-3-methylimidazolium, 1 -Methyl-3-propyl-2,4-dimethylimidazolium, 1,2,3,4-tetramethylimidazolium, 1,2,3,4,5-pentamethylimidazolium, 2-ethyl-1,3 -Dimethylimidazolium, 1,3-dimethyl-2-propylimidazolium, 1,3-dimethyl-2-pentylimidazoli 1,3-dimethyl-2-heptylimidazolium, 1,3,4-trimethylimidazolium, 2-ethyl-1,3,4-trimethylimidazolium, 1,3-dimethylbenzimidazolium, 1-phenyl -3-methylimidazolium, 1-benzyl-3-methylimidazolium, 1-phenyl-2,3-dimethylimidazolium, 1-benzyl-2,3-dimethylimidazolium, 2-phenyl-1,3-dimethyl Imidazolium, 2-benzyl-1,3-dimethylimidazolium, 1,3-dimethyl-2-undecylimidazolium, 1,3-dimethyl-2-heptadecylimidazolium 2- (2′-hydroxy) ethyl- 1,3-dimethylimidazolium, 1- (2′-hydroxy) ethyl-2,3-dimethylimidazolium, - ethoxymethyl-1,3-dimethyl-imidazolium, 1-ethoxy-2,3-but-dimethyl imidazolium and the like, but is not limited thereto.
ピラゾリウムカチオンとしては、１，２−ジメチルピラゾリウム、１，２，３−トリメチルピラゾリウム、１−エチル−２−メチルピラゾリウム、１−エチル−２，３−ジメチルピラゾリウム、１，２−ジエチルピラゾリウム、１，２−ジエチル−３−メチルピラゾリウム、１，３−ジエチル−２−メチルピラゾリウム、１，２−ジメチル−３−プロピルピラゾリウム、１−ブチル−２−メチルピラゾリウム、１−メチル−３−プロピル−２，４−ジメチルピラゾリウム、１，２，３，４−テトラメチルピラゾリウム、１，２，３，４，５−ペンタメチルピラゾリウム、２−エチル−１，３−ジメチルピラゾリウム、１，３−ジメチル−２−プロピルピラゾリウム、１，３−ジメチル−２−ペンチルピラゾリウム、１，３−ジメチル−２−ヘプチルピラゾリウム、１，３，４−トリメチルピラゾリウム、２−エチル−１，３，４−トリメチルピラゾリウム、１，２−ジメチルベンゾピラゾリウム、１−フェニル−２−メチルピラゾリウム、１−ベンジル−２−メチルピラゾリウム、１−フェニル−２，３−ジメチルピラゾリウム、１−ベンジル−２，３−ジメチルピラゾリウム、２−フェニル−１，３−ジメチルピラゾリウム、２−ベンジル−１，３−ジメチルピラゾリウム、１，３−ジメチル−２−ウンデシルピラゾリウム、１，３−ジメチル−２−ヘプタデシルピラゾリウム、２−（２′−ヒドロキシ）エチル−１，３−ジメチルピラゾリウム、１−（２′−ヒドロキシ）エチル−２，３−ジメチルピラゾリウム、２−エトキシメチル−１，３−ジメチルピラゾリウム、１−エトキシメチル−２，３−ジメチルピラゾリウムがあげられるが、これらに限定されるものではない。 Examples of the pyrazolium cation include 1,2-dimethylpyrazolium, 1,2,3-trimethylpyrazolium, 1-ethyl-2-methylpyrazolium, 1-ethyl-2,3-dimethylpyrazolium. 1,2-diethylpyrazolium, 1,2-diethyl-3-methylpyrazolium, 1,3-diethyl-2-methylpyrazolium, 1,2-dimethyl-3-propylpyrazolium, -Butyl-2-methylpyrazolium, 1-methyl-3-propyl-2,4-dimethylpyrazolium, 1,2,3,4-tetramethylpyrazolium, 1,2,3,4,5 -Pentamethylpyrazolium, 2-ethyl-1,3-dimethylpyrazolium, 1,3-dimethyl-2-propylpyrazolium, 1,3-dimethyl-2-pentylpyrazolium, 1,3- Dimethyl-2-he Tilpyrazolium, 1,3,4-trimethylpyrazolium, 2-ethyl-1,3,4-trimethylpyrazolium, 1,2-dimethylbenzopyrazolium, 1-phenyl-2-methylpyrazolium, 1 -Benzyl-2-methylpyrazolium, 1-phenyl-2,3-dimethylpyrazolium, 1-benzyl-2,3-dimethylpyrazolium, 2-phenyl-1,3-dimethylpyrazolium, 2 -Benzyl-1,3-dimethylpyrazolium, 1,3-dimethyl-2-undecylpyrazolium, 1,3-dimethyl-2-heptadecylpyrazolium, 2- (2'-hydroxy) ethyl- 1,3-dimethylpyrazolium, 1- (2′-hydroxy) ethyl-2,3-dimethylpyrazolium, 2-ethoxymethyl-1,3-dimethylpyrazolium, 1-d Kishimechiru -2,3-dimethyl-pyrazolium and the like, but not limited thereto.
チアゾリウムカチオンとしては、Ｎ−メチルチアゾリウム、Ｎ−エチルチアゾリウム、Ｎ−プロピルチアゾリウム、Ｎ−ブチルチアゾリウム、Ｎ−ペンチルチアゾリウム、Ｎ−ヘキシルチアゾリウム、Ｎ−オクチルチアゾリウム、Ｎ−メチル−メチルチアゾリウム、Ｎ−メチル−エチルチアゾリウム、Ｎ−メチル−ブチルチアゾリウム、Ｎ−エチル−メチルチアゾリウム、Ｎ−ブチル−メチルチアゾリウム、Ｎ−ブチルーエチルチアゾリウム、Ｎ−ブチル−プロピルチアゾリウム、Ｎ−ヘキシル−メチルチアゾリウム、Ｎ−オクチル−メチルチアゾリウムなどがあげられるが、これらに限定されるものではない。 Thiazolium cations include N-methylthiazolium, N-ethylthiazolium, N-propylthiazolium, N-butylthiazolium, N-pentylthiazolium, N-hexylthiazolium, N -Octylthiazolium, N-methyl-methylthiazolium, N-methyl-ethylthiazolium, N-methyl-butylthiazolium, N-ethyl-methylthiazolium, N-butyl-methylthiazolium N-butyl-ethylthiazolium, N-butyl-propylthiazolium, N-hexyl-methylthiazolium, N-octyl-methylthiazolium, etc., but are not limited thereto. .
オキサゾリウムカチオンとしては、Ｎ−メチルオキサゾリウム、Ｎ−エチルオキサゾリウム、Ｎ−プロピルオキサゾリウム、Ｎ−ブチルオキサゾリウム、Ｎ−ペンチルオキサゾリウム、Ｎ−ヘキシルオキサゾリウム、Ｎ−オクチルオキサゾリウム、Ｎ−メチル−メチルオキサゾリウム、Ｎ−メチル−エチルオキサゾリウム、Ｎ−メチル−ブチルオキサゾリウム、Ｎ−エチル−メチルオキサゾリウム、Ｎ−ブチル−メチルオキサゾリウム、Ｎ−ブチルーエチルオキサゾリウム、Ｎ−ブチル−プロピルオキサゾリウム、Ｎ−ヘキシル−メチルオキサゾリウム、Ｎ−オクチル−メチルオキサゾリウムなどがあげられるが、これらに限定されるものではない。 Examples of the oxazolium cation include N-methyloxazolium, N-ethyloxazolium, N-propyloxazolium, N-butyloxazolium, N-pentyloxazolium, N-hexyloxazolium, N -Octyloxazolium, N-methyl-methyloxazolium, N-methyl-ethyloxazolium, N-methyl-butyloxazolium, N-ethyl-methyloxazolium, N-butyl-methyloxazolium N-butyl-ethyl oxazolium, N-butyl-propyl oxazolium, N-hexyl-methyl oxazolium, N-octyl-methyl oxazolium, etc., but are not limited thereto. .
上記一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩は、公知のイオン交換法または複分解反応法により製造することができる。例えば、前駆体オニウム塩（例えば、ハロゲン化オニウム、アルカンスルホン酸オニウム、アルカンカルボン酸オニウムまたは水酸化オニウム塩）を、水溶液中で環状パーフルオロアルキレンジスルホンイミド前駆体金属塩または環状パーフルオロアルキレンジスルホンイミド酸と混合させて製造することができる。 The cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1] can be produced by a known ion exchange method or metathesis reaction method. For example, precursor onium salts (eg, onium halides, onium alkanesulfonates, onium alkanecarboxylates or onium hydroxide salts) can be converted into cyclic perfluoroalkylene disulfonimide precursor metal salts or cyclic perfluoroalkylene disulfonimides in aqueous solution. It can be produced by mixing with an acid.
本発明の導電性付与剤は、一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩を単独で用いることもできるが、熱可塑性樹脂またはゴムとの相溶性をよくするため、該環状パーフルオロアルキレンジスルホンイミド塩に末端水酸基を有する樹脂、すなわち、末端水酸基を有するポリエーテルポリオール、末端水酸基を有するポリアルキレングリコール、末端水酸基を有するポリエチレン主鎖とポリアルキレンオキサイドとのグラフト共重合体からなる群から選ばれる少なくとも１種を添加させた後、加熱混練させて用いられる。 As the conductivity-imparting agent of the present invention, the cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1] can be used alone, but in order to improve the compatibility with the thermoplastic resin or rubber, A resin having a terminal hydroxyl group on a perfluoroalkylene disulfonimide salt, that is, a polyether polyol having a terminal hydroxyl group, a polyalkylene glycol having a terminal hydroxyl group, and a graft copolymer of a polyethylene main chain having a terminal hydroxyl group and a polyalkylene oxide. After at least one selected from the group is added, the mixture is heated and kneaded.
一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩に末端水酸基を有する樹脂を添加させる場合、末端水酸基を有する樹脂１００質量部に対して、該環状パーフルオロアルキレンジスルホンイミド塩が１〜５０質量部となる範囲で添加され、添加量が１質量部より未満または５０質量部より超の場合、導電性が低下し不都合である。 When the resin having a terminal hydroxyl group is added to the cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1], the cyclic perfluoroalkylene disulfonimide salt is 1 to 100 parts by mass of the resin having a terminal hydroxyl group. When it is added in the range of 50 parts by mass and the addition amount is less than 1 part by mass or more than 50 parts by mass, the conductivity is disadvantageously lowered.
次に、本発明の導電性樹脂組成物について詳細に説明する。 Next, the conductive resin composition of the present invention will be described in detail.
本発明の導電性樹脂組成物は、熱可塑性樹脂またはゴムに、本発明の導電性付与剤が添加されてなるものである。 The conductive resin composition of the present invention is obtained by adding the conductivity imparting agent of the present invention to a thermoplastic resin or rubber.
本発明に用いられる熱可塑性樹脂としては、例えば、ポリエチレン、ポリプロピレン、ポリスチレン等のポリオレフィン系樹脂及びその組成物、ポリアセタール、ポリアクリレート、アクリル樹脂及びその組成物、ポリフェニレンエーテル（以下、「ＰＰＥ」と略記する。）、ＰＰＥ／ポリスチレン、ＰＰＥ／ポリアミド（以下、「ＰＡ」と略記する。）、ＰＰＥ／ポリブチレンテレフタレート（以下、「ＰＢＴ」と略記する。）等のポリフェニレンエーテル系樹脂及びその組成物、ポリエーテルケトン、ポリエチレンテレフタレート（以下、「ＰＥＴ」と略記する。）、ＰＢＴ／ＡＢＳ等のポリエステル系樹脂及びその組成物、ポリカーボネート（以下、「ＰＣ」と略記する。）、ＰＣ／ＡＢＳ、ＰＣ／ＰＥＴ、ＰＣ／ＰＢＴ等のポリカーボネート系樹脂及びその組成物、ポリウレタン及びその組成物、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリイミド、ポリエーテルイミド、ポリアミドイミド、ポリフェニレンサルファイド系樹脂及びその組成物、ポリサルホンがあげられる。 Examples of the thermoplastic resin used in the present invention include polyolefin resins such as polyethylene, polypropylene, and polystyrene and compositions thereof, polyacetals, polyacrylates, acrylic resins and compositions thereof, and polyphenylene ether (hereinafter abbreviated as “PPE”). Polyphenylene ether-based resins such as PPE / polystyrene, PPE / polyamide (hereinafter abbreviated as “PA”), PPE / polybutylene terephthalate (hereinafter abbreviated as “PBT”), and compositions thereof, Polyether ketone, polyethylene terephthalate (hereinafter abbreviated as “PET”), polyester resins such as PBT / ABS and compositions thereof, polycarbonate (hereinafter abbreviated as “PC”), PC / ABS, PC / Polycarbonate such as PET, PC / PBT Sulphonate resins and compositions thereof, polyurethanes and compositions thereof, polyvinyl chloride, polyvinylidene chloride, polyimide, polyetherimide, polyamideimide, polyphenylene sulfide-based resin and its composition, the polysulfone and the like.
導電性に優れる点から、アクリル樹脂、ポリエステル樹脂、ポリアミド樹脂、ポリウレタン樹脂、ポリ塩化ビニル、エポキシ樹脂が好ましく、これらの樹脂の少なくとも１種が用いられる。 From the viewpoint of excellent conductivity, acrylic resin, polyester resin, polyamide resin, polyurethane resin, polyvinyl chloride, and epoxy resin are preferable, and at least one of these resins is used.
また、本発明に用いられるゴムとしては、ウレタンゴム、アクリルゴム、アクリロニトリル−ブタジエンゴム、エピクロルヒドリンゴム、エピクロルヒドリン−エチレンオキサイド共重合ゴム、シリコンゴム、フルオロオレフィンビニルエーテル共重合体ウレタンゴム、スチレンブタジエン共重合体ゴム及びそれらの発泡体からなる群から選ばれる少なくとも１種があげられる。 The rubber used in the present invention includes urethane rubber, acrylic rubber, acrylonitrile-butadiene rubber, epichlorohydrin rubber, epichlorohydrin-ethylene oxide copolymer rubber, silicon rubber, fluoroolefin vinyl ether copolymer urethane rubber, styrene butadiene copolymer. Examples thereof include at least one selected from the group consisting of rubber and foams thereof.
本発明の導電性樹脂組成物は、熱可塑性樹脂またはゴムに、本発明の導電性付与剤を所定量添加、混練し、フィルム状、シート状あるいはロール状等に成形して用いられる。 The conductive resin composition of the present invention is used by adding a predetermined amount of the conductivity-imparting agent of the present invention to a thermoplastic resin or rubber and kneading it into a film, sheet or roll.
上記導電性樹脂組成物中における導電性付与剤では、熱可塑性樹脂またはゴム１００質量部に対して、イオン導電剤である一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩が０．１〜２０質量部となる範囲で添加される。０．１質量部より未満の場合、得られた導電性樹脂組成物の導電性が不十分であり、また、２０質量部より超の場合、導電性は十分であるがブリードを発生しやすくなり不都合である。 In the electroconductivity imparting agent in the conductive resin composition, the cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1], which is an ionic conductive agent, is 0.1% relative to 100 parts by mass of the thermoplastic resin or rubber. It is added in a range of 1 to 20 parts by mass. If the amount is less than 0.1 parts by mass, the resulting conductive resin composition has insufficient conductivity. If the amount is more than 20 parts by mass, the conductivity is sufficient but bleeding tends to occur. It is inconvenient.
本発明の導電性付与剤は、イオン導電性の高い一般式〔１〕で表される環状パーフルオロアルキレンジスルホンイミド塩が含有されており、該導電性付与剤が添加された導電性樹脂組成物は、ブリードによるイオン導電剤のしみ出しがなく、導電性、柔軟性に優れ、また長期間安定した特性が発現できる。 The conductivity-imparting agent of the present invention contains a cyclic perfluoroalkylene disulfonimide salt represented by the general formula [1] having high ionic conductivity, and a conductive resin composition to which the conductivity-imparting agent is added. Does not exude an ionic conductive agent due to bleeding, has excellent conductivity and flexibility, and can exhibit stable characteristics for a long period of time.
以下、本発明の実施の形態を、実施例に基づいて説明する。なお、本発明は実施例によりなんら限定されない。なお、実施例中の「部」は「質量部」を表す。 Hereinafter, embodiments of the present invention will be described based on examples. In addition, this invention is not limited at all by the Example. In the examples, “part” represents “part by mass”.
実施例１
末端水酸基を有するポリエチレン主鎖とポリアルキレンオキサイドのグラフト重合体（分子量４０００、住友化学工業（株）登録商標：スミエード３００Ｇ）９０部に、イオン導電剤であるテトラメチルアンモニウム１，３−ヘキサフルオロプロピレンジスルホニルイミド塩２０部を加えた後、温度７０℃で加熱混練させて導電性付与剤を得た。
Example 1
Polyethylene main chain having a terminal hydroxyl group and polyalkylene oxide graft polymer (molecular weight 4000, Sumitomo Chemical Co., Ltd., registered trademark: Sumiade 300G) 90 parts of tetramethylammonium 1,3-hexafluoropropylene as an ionic conductive agent After adding 20 parts of disulfonylimide salt, the mixture was heated and kneaded at a temperature of 70 ° C. to obtain a conductivity-imparting agent.
ついで、熱可塑性樹脂であるアクリル樹脂（三菱レーヨン（株）登録商標：アクリペットＩＲ Ｈ−７０）１００部に、先に得られた導電性付与剤２０部を添加し、テストロール機（日新科学（株）製ＨＲ−２型）中、温度１００℃で加熱混練させて、厚さ１ｍｍの導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は３．６部である。 Next, 20 parts of the previously obtained conductivity-imparting agent was added to 100 parts of acrylic resin (Mitsubishi Rayon Co., Ltd .: Acrypet IR H-70) which is a thermoplastic resin, and a test roll machine (Nisshin) Heat-kneaded at a temperature of 100 ° C. in Scientific Co., Ltd. (HR-2 type) to obtain a 1 mm thick conductive sheet. In the conductive sheet, the addition amount of the ionic conductive agent is 3.6 parts with respect to 100 parts of the thermoplastic resin.
得られた導電性シートの表面抵抗を表面抵抗測定機（三菱化学（株）製ＨＴ−２１０）を用いて測定した。また、導電性シートを２つに折り曲げて、温度４０℃、湿度８０％の環境下で、９０日間放置した後、イオン導電剤のしみ出しを目視により表面観察し、ブリードの有無を調べた。結果を表１に示す。 The surface resistance of the obtained conductive sheet was measured using a surface resistance measuring machine (HT-210 manufactured by Mitsubishi Chemical Corporation). Further, the conductive sheet was folded in two and allowed to stand for 90 days in an environment at a temperature of 40 ° C. and a humidity of 80%, and then the surface of the ionic conductive agent was visually observed to check for the presence of bleeding. The results are shown in Table 1.
実施例２
実施例１に準じて、スミエード３００Ｇ ９０部に、イオン導電剤である、Ｎ，Ｎ−ジエチルピロリジニウム１，３−ヘキサフルオロプロピレンジスルホニルイミド塩３０部を加えた後、温度７０℃で加熱混練させて導電性付与剤を得た。
Example 2
According to Example 1, 30 parts of N, N-diethylpyrrolidinium 1,3-hexafluoropropylene disulfonylimide salt, which is an ionic conductive agent, was added to 90 parts of Sumiade 300G, and then heated at a temperature of 70 ° C. The conductivity imparting agent was obtained by kneading.
ついで、熱可塑性樹脂であるポリウレタン樹脂（大日本インキ化学工業（株）登録商標：パンデックスＴ−８１９０Ｎ）１００部に、先に得られた導電性付与剤４０部を添加し、テストロール機中、温度１８０℃で加熱混練させて、厚さ１ｍｍの導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は１０部である。 Next, 40 parts of the conductivity-imparting agent obtained above was added to 100 parts of a polyurethane resin (Dainippon Ink and Chemicals, Inc., registered trademark: Pandex T-8190N), which is a thermoplastic resin, and in a test roll machine. The mixture was heated and kneaded at a temperature of 180 ° C. to obtain a conductive sheet having a thickness of 1 mm. In the conductive sheet, the addition amount of the ionic conductive agent is 10 parts with respect to 100 parts of the thermoplastic resin.
以下、実施例１と同様にして表面抵抗及びブリードの有無を調べた。結果を表１に示す。 Thereafter, the surface resistance and the presence or absence of bleed were examined in the same manner as in Example 1. The results are shown in Table 1.
実施例３
実施例１に準じて、ポリエチレングリコールとポリプロピレングリコールのブロック共重合体（日本油脂（株）登録商標：プロノン１０２）１００部に、イオン導電剤である１，２−ジエチル−３−メチルイミダゾリウム−１，３−ヘキサフルオロプロピレンジスルホニルイミド塩１０部を加えた後、温度７０℃で加熱混練させて導電性付与剤を得た。
Example 3
According to Example 1, 100 parts of a block copolymer of polyethylene glycol and polypropylene glycol (Nippon Yushi Co., Ltd .: Pronon 102) was added to 1,2-diethyl-3-methylimidazolium as an ionic conductive agent. After adding 10 parts of 1,3-hexafluoropropylene disulfonylimide salt, the mixture was heated and kneaded at a temperature of 70 ° C. to obtain a conductivity-imparting agent.
ついで、熱可塑性樹脂であるポリエステル樹脂（大日本インキ化学工業（株）製ポリブチレンテレフタレート）１００部に、先に得られた導電性付与剤４０部を添加し、テストロール機中、温度２５０℃で加熱混練させて、厚さ１ｍｍの導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は３．６部である。 Next, 40 parts of the conductivity-imparting agent obtained above was added to 100 parts of a polyester resin (polybutylene terephthalate manufactured by Dainippon Ink & Chemicals, Inc.) which is a thermoplastic resin, and the temperature was 250 ° C. in a test roll machine. The mixture was heated and kneaded to obtain a conductive sheet having a thickness of 1 mm. In the conductive sheet, the addition amount of the ionic conductive agent is 3.6 parts with respect to 100 parts of the thermoplastic resin.
以下、実施例１と同様にして表面抵抗及びブリードの有無を調べた。結果を表１に示す。 Thereafter, the surface resistance and the presence or absence of bleed were examined in the same manner as in Example 1. The results are shown in Table 1.
実施例４
実施例１に準じて、ポリエチレングリコールとポリプロピレングリコールのブロック共重合体（プロノン１０２）９０部に、イオン導電剤であるＮ−ブチル−メチルピリジニウム−１，３−ヘキサフルオロプロピレンジスルホニルイミド酸５部を加えた後、温度７０℃で加熱混練させて導電性付与剤を得た。
Example 4
According to Example 1, 5 parts of N-butyl-methylpyridinium-1,3-hexafluoropropylene disulfonylimide acid, which is an ionic conductive agent, are added to 90 parts of a block copolymer of polyethylene glycol and polypropylene glycol (Pronon 102). Then, the mixture was heated and kneaded at a temperature of 70 ° C. to obtain a conductivity-imparting agent.
ついで、熱可塑性樹脂であるポリアミド樹脂（ナイロン６１２：ダイセルヒュルス（株）登録商標：ダイアナミド１７００）１００部に、先に得られた導電性付与剤１０部を添加し、テストロール機中、温度２２０℃で加熱混練させて、厚さ１ｍｍの導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は０．５部である。 Next, 10 parts of the conductivity-imparting agent obtained above is added to 100 parts of a polyamide resin (nylon 612: Daicel Huls Co., Ltd .: Dyanamide 1700) which is a thermoplastic resin. Heat kneading was performed at 220 ° C. to obtain a conductive sheet having a thickness of 1 mm. In the conductive sheet, the addition amount of the ionic conductive agent is 0.5 part with respect to 100 parts of the thermoplastic resin.
以下、実施例１と同様にして表面抵抗及びブリードの有無を調べた。結果を表１に示す。 Thereafter, the surface resistance and the presence or absence of bleed were examined in the same manner as in Example 1. The results are shown in Table 1.
比較例１
実施例１において、イオン導電剤として過塩素酸リチウム２０部を用いた以外は実施例１と同様にして導電性付与剤を得、また、実施例１と同様にして導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は３．６部である。
Comparative Example 1
In Example 1, a conductivity imparting agent was obtained in the same manner as in Example 1 except that 20 parts of lithium perchlorate was used as the ionic conductive agent, and a conductive sheet was obtained in the same manner as in Example 1. In the conductive sheet, the addition amount of the ionic conductive agent is 3.6 parts with respect to 100 parts of the thermoplastic resin.
以下、実施例１と同様にして表面抵抗及びブリードの有無を調べた。結果を表１に示す。 Thereafter, the surface resistance and the presence or absence of bleed were examined in the same manner as in Example 1. The results are shown in Table 1.
比較例２
実施例２において、イオン導電剤として過ヨウ素酸テトラエチルアンモニウム４０部を用いた以外は実施例２と同様にして導電性付与剤を得、実施例２と同様にして導電性シートを得た。該導電性シートは、熱可塑性樹脂１００部に対して、イオン導電剤の添加量は１２．３部である。
Comparative Example 2
In Example 2, a conductivity imparting agent was obtained in the same manner as in Example 2 except that 40 parts of tetraethylammonium periodate was used as the ionic conductive agent, and a conductive sheet was obtained in the same manner as in Example 2. In the conductive sheet, the addition amount of the ionic conductive agent is 12.3 parts with respect to 100 parts of the thermoplastic resin.
以下、実施例１と同様にして表面抵抗及びブリードの有無を調べた。結果を表１に示す。 Thereafter, the surface resistance and the presence or absence of bleed were examined in the same manner as in Example 1. The results are shown in Table 1.
実施例５
発泡性ゴムであるウレタン（日本ポリウレタン工業（株）登録商標：ニッポラン５１９９、以下「Ｕ」と略記する。）１００部に、イオン導電剤であるトリメチルメトキシエチルアンモニウム−１，３−ヘキサフルオロプロピレンジスルホニルイミド塩８部を加え、加熱混練により発泡及び架橋させた後、成型用金型に流し込み、厚み１２ｍｍの導電性発泡ゴム成形体を得た。
Example 5
100 parts of urethane, which is a foaming rubber (Nippon Polyurethane Industry Co., Ltd., registered trademark: NIPPOLAN 5199, hereinafter abbreviated as “U”), is added to trimethylmethoxyethylammonium-1,3-hexafluoropropylenedi, which is an ionic conductive agent After adding 8 parts of sulfonylimide salt and foaming and crosslinking by heating and kneading, it was poured into a molding die to obtain a conductive foamed rubber molded body having a thickness of 12 mm.
得られた該成形体について、（財）日本工業規格ＪＩＳ Ｋ６２５３に準じてゴム硬度を測定した。また、比抵抗測定器により、比抵抗を測定した。これらの結果を表２に示す。 About the obtained molding, rubber hardness was measured according to Japan Industrial Standard JIS K6253. Moreover, the specific resistance was measured with a specific resistance measuring instrument. These results are shown in Table 2.
実施例６
実施例５において、イオン導電剤としてＮ，Ｎ−メチルエチルモルホニウム−１，３−ヘキサフルオロプロピレンジスルホニルイミド塩５部を用いた以外は実施例５と同様にして、導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Example 6
In Example 5, conductive foam rubber molding was carried out in the same manner as in Example 5 except that 5 parts of N, N-methylethylmorphonium-1,3-hexafluoropropylene disulfonylimide salt was used as the ionic conductive agent. Got the body. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
実施例７
実施例５において、発泡性ゴムとしてエピクロルヒドリンゴム（ダイソー（株）製エピクロマーＣＧ―１０２、以下「ＥＰ」と略記する。）１００部を、また、イオン導電剤としてＮ−ヘキシル−メチルピリジニウム１，３−ヘキサフルオロプロピレンジスルホニルイミド塩４部を用いた以外は実施例５と同様にして導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Example 7
In Example 5, 100 parts of epichlorohydrin rubber (Daiso Co., Ltd. Epichromer CG-102, hereinafter abbreviated as “EP”) as the foamable rubber, and N-hexyl-methylpyridinium 1,3 as the ionic conductive agent were used. -A conductive foamed rubber molded article was obtained in the same manner as in Example 5 except that 4 parts of hexafluoropropylene disulfonylimide salt was used. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
実施例８
実施例５において、発泡性ゴムとしてアクリル（ＪＳＲ(株)製アクリルラテッックスＡＥ８３２、以下「ＡＣＭ」と略記する。）１００部を、また、イオン導電剤としてＮ−ブチル−メチルチアゾリウム１，３−ヘキサフルオロプロピレンジスルホニルイミド塩３部を用いた以外は実施例５と同様にして導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Example 8
In Example 5, 100 parts of acrylic (acrylic latex AE832, manufactured by JSR Corporation, hereinafter abbreviated as “ACM”) as the foamable rubber, and N-butyl-methylthiazolium 1 as the ionic conductive agent were used. , 3-hexafluoropropylene disulfonylimide salt was used in the same manner as in Example 5 except that 3 parts of a conductive foamed rubber molded article was obtained. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
比較例３
実施例５において、導電剤としてカーボンブラック３０部を用いた以外は実施例５と同様にして、導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Comparative Example 3
In Example 5, a conductive foamed rubber molded article was obtained in the same manner as in Example 5 except that 30 parts of carbon black was used as the conductive agent. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
比較例４
実施例５において、イオン導電剤として過塩素酸リチウム２部を用いた以外は実施例５と同様にして、導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Comparative Example 4
In Example 5, a conductive foamed rubber molding was obtained in the same manner as in Example 5 except that 2 parts of lithium perchlorate was used as the ionic conductive agent. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
比較例５
実施例５において、発泡性ゴムとしてＥＰ１００部、導電剤として酸化チタン（石原産業（株）登録商標：タイペークＥＴ５００Ｗ）２０部を用いた以外は実施例５と同様にして、導電性発泡ゴム成形体を得た。該成形体のゴム硬度及び比抵抗測定結果を表２に示す。
Comparative Example 5
In Example 5, a conductive foam rubber molded body was obtained in the same manner as in Example 5, except that EP 100 parts was used as the foam rubber and 20 parts titanium oxide (registered trademark of Ishihara Sangyo Co., Ltd .: Taipei ET 500W) was used as the conductive agent. Got. Table 2 shows the rubber hardness and specific resistance measurement results of the molded body.
表１に示すように、比較例１及び２では、表面抵抗が高くブリードの発生が見られたのに対して、環状パーフルオロアルキレンジスルホンイミド塩を含む本発明の導電性付与剤が添加された実施例１〜４に示す導電シートは、表面抵抗が低く、ブリードの発生が観察されなかった。 As shown in Table 1, in Comparative Examples 1 and 2, although the surface resistance was high and bleeding was observed, the conductivity-imparting agent of the present invention containing a cyclic perfluoroalkylene disulfonimide salt was added. The conductive sheets shown in Examples 1 to 4 had low surface resistance, and no bleed was observed.
また、表２に示すように、導電性付与剤としてカーボンブラック、過塩素酸リチウム、酸化チタンが添加された比較例３〜５の導電性発泡ゴムは、ゴム硬度が高く、比抵抗が高いのに対し、本発明の導電性付与剤が添加された実施例５〜８の導電性発泡ゴムは、ゴム硬度が低くかつ比抵抗が低く、柔軟性、導電性に優れている。 Moreover, as shown in Table 2, the conductive foamed rubbers of Comparative Examples 3 to 5 to which carbon black, lithium perchlorate, and titanium oxide are added as conductivity imparting agents have high rubber hardness and high specific resistance. On the other hand, the conductive foamed rubbers of Examples 5 to 8 to which the conductivity-imparting agent of the present invention is added have low rubber hardness and low specific resistance, and are excellent in flexibility and conductivity.
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