CN102532866A - Semi-conductive resin composition - Google Patents
Semi-conductive resin composition Download PDFInfo
- Publication number
- CN102532866A CN102532866A CN2011103687784A CN201110368778A CN102532866A CN 102532866 A CN102532866 A CN 102532866A CN 2011103687784 A CN2011103687784 A CN 2011103687784A CN 201110368778 A CN201110368778 A CN 201110368778A CN 102532866 A CN102532866 A CN 102532866A
- Authority
- CN
- China
- Prior art keywords
- cation
- alkyl
- ion
- semi
- methyl
- 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.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 24
- 150000002500 ions Chemical class 0.000 claims abstract description 40
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 150000002466 imines Chemical class 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims description 67
- -1 sulfonium cations Chemical class 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 230000007704 transition Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- CEWNCDBHUYUXFA-UHFFFAOYSA-N 2-methyl-1-octyl-2H-pyridine Chemical compound CC1N(C=CC=C1)CCCCCCCC CEWNCDBHUYUXFA-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- NHQMOOZIVSRONZ-UHFFFAOYSA-N 4-methyl-1-octyl-2H-pyridine Chemical compound C(CCCCCCC)N1CC=C(C=C1)C NHQMOOZIVSRONZ-UHFFFAOYSA-N 0.000 claims 1
- 239000006258 conductive agent Substances 0.000 abstract description 13
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000009477 glass transition Effects 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 241000723346 Cinnamomum camphora Species 0.000 description 6
- 229930008380 camphor Natural products 0.000 description 6
- 239000002608 ionic liquid Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 6
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 5
- 229960000846 camphor Drugs 0.000 description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 3
- SSGBLFZLLLQTNF-UHFFFAOYSA-N 1,2,3-trimethyl-2,4-dihydropyrimidine Chemical compound CC1N(C)CC=CN1C SSGBLFZLLLQTNF-UHFFFAOYSA-N 0.000 description 2
- VUHMIPWBDMGTNL-MHCZMQLOSA-N 1,2-dimethoxy-4-[(e)-prop-1-enyl]benzene;1,2,4-trimethoxy-5-[(e)-prop-1-enyl]benzene Chemical compound COC1=CC=C(\C=C\C)C=C1OC.COC1=CC(OC)=C(\C=C\C)C=C1OC VUHMIPWBDMGTNL-MHCZMQLOSA-N 0.000 description 2
- UPCMWHVBPPBFPF-UHFFFAOYSA-N 1,3-dimethyl-2,4-dihydropyrimidine Chemical compound CN1CC=CN(C)C1 UPCMWHVBPPBFPF-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- GFVKHYGXCQWRON-UHFFFAOYSA-N tributyl(ethyl)azanium Chemical compound CCCC[N+](CC)(CCCC)CCCC GFVKHYGXCQWRON-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- NFHJHLHQVOUCLC-UHFFFAOYSA-N 1,2,3,4-tetramethyl-1,3-diazinane Chemical compound CC1CCN(C)C(C)N1C NFHJHLHQVOUCLC-UHFFFAOYSA-N 0.000 description 1
- JSVJUBWXVYOSIG-UHFFFAOYSA-N 1,2,3,4-tetramethyl-2,4-dihydropyrimidine Chemical compound CC1C=CN(C)C(C)N1C JSVJUBWXVYOSIG-UHFFFAOYSA-N 0.000 description 1
- YOOLJTBTGUJKSI-UHFFFAOYSA-N 1,2,3,5-tetramethyl-1,3-diazinane Chemical compound CC1CN(C)C(C)N(C)C1 YOOLJTBTGUJKSI-UHFFFAOYSA-N 0.000 description 1
- HZZZJWRCCWTBHD-UHFFFAOYSA-N 1,2,3,6-tetramethyl-2,4-dihydropyrimidine Chemical compound CC1N(C)CC=C(C)N1C HZZZJWRCCWTBHD-UHFFFAOYSA-N 0.000 description 1
- GRHNKLNJAYKFIG-UHFFFAOYSA-N 1,2,3-trimethyl-1,3-diazinane Chemical compound CC1N(C)CCCN1C GRHNKLNJAYKFIG-UHFFFAOYSA-N 0.000 description 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 1
- ALSIFQIAIHCPAA-UHFFFAOYSA-N 1,2-dimethyl-3-propyl-2h-imidazole Chemical compound CCCN1C=CN(C)C1C ALSIFQIAIHCPAA-UHFFFAOYSA-N 0.000 description 1
- RYNROCNODWBDCM-UHFFFAOYSA-N 1,3-diethyl-2h-imidazole Chemical compound CCN1CN(CC)C=C1 RYNROCNODWBDCM-UHFFFAOYSA-N 0.000 description 1
- DCPLDPXQOOHYSU-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane Chemical compound CN1CCCN(C)C1 DCPLDPXQOOHYSU-UHFFFAOYSA-N 0.000 description 1
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 1
- WGVGZVWOOMIJRK-UHFFFAOYSA-N 1-hexyl-3-methyl-2h-imidazole Chemical compound CCCCCCN1CN(C)C=C1 WGVGZVWOOMIJRK-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- OQJRUUUFRQCENE-UHFFFAOYSA-N 1-octylpiperidine Chemical compound CCCCCCCCN1CCCCC1 OQJRUUUFRQCENE-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- AHGSHJZSOASAKV-UHFFFAOYSA-N 2-(2-ethylhexyl)pyridine Chemical compound CCCCC(CC)CC1=CC=CC=N1 AHGSHJZSOASAKV-UHFFFAOYSA-N 0.000 description 1
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BMOTZWRARKOFOU-UHFFFAOYSA-N C(C=C)(=O)N(CCCCCCCC(C)C)C Chemical compound C(C=C)(=O)N(CCCCCCCC(C)C)C BMOTZWRARKOFOU-UHFFFAOYSA-N 0.000 description 1
- QYGNWDWNZBZHMD-UHFFFAOYSA-N CN(C)C(=NO)C(C1=CC=CC=C1)=O Chemical compound CN(C)C(=NO)C(C1=CC=CC=C1)=O QYGNWDWNZBZHMD-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQXNXVUDBPYKBA-UHFFFAOYSA-N Ectoine Natural products CC1=NCCC(C(O)=O)N1 WQXNXVUDBPYKBA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005250 beta ray Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- MPCVYAVDVXEPTK-UHFFFAOYSA-N butane Chemical compound CCC[CH2+] MPCVYAVDVXEPTK-UHFFFAOYSA-N 0.000 description 1
- AILPSZWICOHGMA-UHFFFAOYSA-N butyl-dimethyl-propylazanium Chemical compound CCCC[N+](C)(C)CCC AILPSZWICOHGMA-UHFFFAOYSA-N 0.000 description 1
- MKLCNZGZWCQCIY-UHFFFAOYSA-N butyl-heptyl-dimethylazanium Chemical compound CCCCCCC[N+](C)(C)CCCC MKLCNZGZWCQCIY-UHFFFAOYSA-N 0.000 description 1
- GUZLSXNNIAYDHJ-UHFFFAOYSA-N butyl-hexyl-dimethylazanium Chemical compound CCCCCC[N+](C)(C)CCCC GUZLSXNNIAYDHJ-UHFFFAOYSA-N 0.000 description 1
- HEZLPXHJHDDYOE-UHFFFAOYSA-N butyl-hexyl-dipropylazanium Chemical compound CCCCCC[N+](CCC)(CCC)CCCC HEZLPXHJHDDYOE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical compound [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 description 1
- RKMJXTWHATWGNX-UHFFFAOYSA-N decyltrimethylammonium ion Chemical compound CCCCCCCCCC[N+](C)(C)C RKMJXTWHATWGNX-UHFFFAOYSA-N 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- USXXKLJKCGLODH-UHFFFAOYSA-N dibutyl-hexyl-methylazanium Chemical compound CCCCCC[N+](C)(CCCC)CCCC USXXKLJKCGLODH-UHFFFAOYSA-N 0.000 description 1
- CJMALQPKCBISHD-UHFFFAOYSA-N dibutyl-methyl-pentylazanium Chemical compound CCCCC[N+](C)(CCCC)CCCC CJMALQPKCBISHD-UHFFFAOYSA-N 0.000 description 1
- BXHHZLMBMOBPEH-UHFFFAOYSA-N diethyl-(2-methoxyethyl)-methylazanium Chemical compound CC[N+](C)(CC)CCOC BXHHZLMBMOBPEH-UHFFFAOYSA-N 0.000 description 1
- PIODCVYLDQEZFW-UHFFFAOYSA-N diethyl-heptyl-methylazanium Chemical compound CCCCCCC[N+](C)(CC)CC PIODCVYLDQEZFW-UHFFFAOYSA-N 0.000 description 1
- OBRWMJNKKIMAPZ-UHFFFAOYSA-N diethyl-methyl-pentylazanium Chemical compound CCCCC[N+](C)(CC)CC OBRWMJNKKIMAPZ-UHFFFAOYSA-N 0.000 description 1
- KSRKBDUROZKZBR-UHFFFAOYSA-N diethyl-methyl-propylazanium Chemical compound CCC[N+](C)(CC)CC KSRKBDUROZKZBR-UHFFFAOYSA-N 0.000 description 1
- IAYWJKSKVFOMDT-UHFFFAOYSA-N diethyl-pentyl-propylazanium Chemical compound CCCCC[N+](CC)(CC)CCC IAYWJKSKVFOMDT-UHFFFAOYSA-N 0.000 description 1
- BVYKZCWFDFGEDY-UHFFFAOYSA-N dihexyl(dimethyl)azanium Chemical compound CCCCCC[N+](C)(C)CCCCCC BVYKZCWFDFGEDY-UHFFFAOYSA-N 0.000 description 1
- JCWIHQGUAVBVND-UHFFFAOYSA-N dihexyl(dipropyl)azanium Chemical compound CCCCCC[N+](CCC)(CCC)CCCCCC JCWIHQGUAVBVND-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- WQHRRUZRGXLCGL-UHFFFAOYSA-N dimethyl(dipropyl)azanium Chemical compound CCC[N+](C)(C)CCC WQHRRUZRGXLCGL-UHFFFAOYSA-N 0.000 description 1
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 description 1
- AEVGDMCWEJJJPC-UHFFFAOYSA-N dimethyl-pentyl-propylazanium Chemical compound CCCCC[N+](C)(C)CCC AEVGDMCWEJJJPC-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- WQXNXVUDBPYKBA-YFKPBYRVSA-N ectoine Chemical compound CC1=[NH+][C@H](C([O-])=O)CCN1 WQXNXVUDBPYKBA-YFKPBYRVSA-N 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- GMFVWRLWYQFTJD-UHFFFAOYSA-N ethyl-dimethyl-nonylazanium Chemical compound CCCCCCCCC[N+](C)(C)CC GMFVWRLWYQFTJD-UHFFFAOYSA-N 0.000 description 1
- DJCZADVNBUGGRS-UHFFFAOYSA-N ethyl-dimethyl-pentylazanium Chemical compound CCCCC[N+](C)(C)CC DJCZADVNBUGGRS-UHFFFAOYSA-N 0.000 description 1
- ZOZZQPFBMNNPPO-UHFFFAOYSA-N ethyl-dimethyl-propylazanium Chemical compound CCC[N+](C)(C)CC ZOZZQPFBMNNPPO-UHFFFAOYSA-N 0.000 description 1
- KUDSOEFZHRAMEU-UHFFFAOYSA-N ethyl-heptyl-dimethylazanium Chemical compound CCCCCCC[N+](C)(C)CC KUDSOEFZHRAMEU-UHFFFAOYSA-N 0.000 description 1
- BEURYHDWKDICEO-UHFFFAOYSA-N ethyl-hexyl-dimethylazanium Chemical compound CCCCCC[N+](C)(C)CC BEURYHDWKDICEO-UHFFFAOYSA-N 0.000 description 1
- YZCTWRWJKAZUIJ-UHFFFAOYSA-N ethyl-methyl-dipropylazanium Chemical compound CCC[N+](C)(CC)CCC YZCTWRWJKAZUIJ-UHFFFAOYSA-N 0.000 description 1
- HDGUMDFPVDXMFR-UHFFFAOYSA-N ethyl-methyl-pentyl-propylazanium Chemical compound CCCCC[N+](C)(CC)CCC HDGUMDFPVDXMFR-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- PISCILXZPLTTFP-UHFFFAOYSA-N heptyl(trimethyl)azanium Chemical compound CCCCCCC[N+](C)(C)C PISCILXZPLTTFP-UHFFFAOYSA-N 0.000 description 1
- HRVTXKZFPPCSKD-UHFFFAOYSA-N heptyl-dimethyl-propylazanium Chemical compound CCCCCCC[N+](C)(C)CCC HRVTXKZFPPCSKD-UHFFFAOYSA-N 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
- KIVAZLJKZWJKRY-UHFFFAOYSA-N hexyl-dimethyl-pentylazanium Chemical compound CCCCCC[N+](C)(C)CCCCC KIVAZLJKZWJKRY-UHFFFAOYSA-N 0.000 description 1
- LZHJKZALMMLMRU-UHFFFAOYSA-N hexyl-dimethyl-propylazanium Chemical compound CCCCCC[N+](C)(C)CCC LZHJKZALMMLMRU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HYYUVNFATOSGPP-UHFFFAOYSA-N methyl-pentyl-dipropylazanium Chemical compound CCCCC[N+](C)(CCC)CCC HYYUVNFATOSGPP-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 230000003287 optical effect Effects 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 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
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- MEJYOZOPFBOWNM-UHFFFAOYSA-N triethyl(heptyl)azanium Chemical compound CCCCCCC[N+](CC)(CC)CC MEJYOZOPFBOWNM-UHFFFAOYSA-N 0.000 description 1
- NFRBUOMQJKUACC-UHFFFAOYSA-N triethyl(pentyl)azanium Chemical compound CCCCC[N+](CC)(CC)CC NFRBUOMQJKUACC-UHFFFAOYSA-N 0.000 description 1
- WGYXSYLSCVXFDU-UHFFFAOYSA-N triethyl(propyl)azanium Chemical compound CCC[N+](CC)(CC)CC WGYXSYLSCVXFDU-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention provides a semi-conductive resin composition, which comprises resin whose glass-transition temperature is lower than 45 DEG and an ion pair whose anion is double (fluorin-sulfonyl) imine and melting point is lower than 20 DEG. The ion pair comprises over one positive ion selected from a nitrogen positive ion, a sulfonium positive ion. Accordingly, conductive agent can be easily and evenly mixed with resin, and when producing a semi-conductive roller, resistance value can be uniformed and stabilized on the whole face of a product.
Description
Technical field
The present invention relates to semi-conducting resin composition, relate to use specific ion pair as conductive agent, can be used in and obtain the elastomeric semi-conducting resin composition of semi-conductivity.
Background technology
OA such as duplicating machine, printer equipment through roller charged, remove electricity and form image.Therefore, pair roller requires semi-conductivity.But the insulativity of rubber and plastics class is high usually, therefore, in order to have semi-conductivity, in resin, adds the conductive agent with ionic or electron conduction.As conductive agent, be generally electrical conductivity Carbon black, but in recent years, also use boron complex salt, lithium salts etc.
For example, the conductive resin composition that comprises the ionic conductive agent that contains specific boron complex is disclosed in patent documentation 1.But, therefore insufficient because this ionic conductive agent is a solid with the intermiscibility of resin, thereby, the shortcoming that can not obtain desired conductivity had.
On the other hand, the conductive elastic roller of use lithium salts as ionic conductive agent disclosed in patent documentation 2.But, because lithium salts has water absorbability, therefore, aspect difficult treatment and electrical characteristic etc. had problems by the aspect of moisture.
Patent documentation 1: the spy of Japan opens the 2008-127483 communique
Patent documentation 2: the spy of Japan opens the 2008-122858 communique
Summary of the invention
Except above-mentioned, there is following problem in the conductive agent that in conductive resin composition in the past, uses: become inhomogeneous when not having well dispersed, be difficult to dissolving, addition is rolled up etc.
The present invention carries out in view of such problem; Its purpose is to provide a kind of semi-conducting resin composition; It can make conductive agent mix easily and equably with resin; When moulding article such as manufacturing semi-conductivity resilient roller, can on whole of moulding article, make the even and stabilization of resistance value thus.
In order to solve above-mentioned problem, it is that resin and negatively charged ion below 45 ℃ is the ion pair below 20 ℃ for two (fluorine sulphonyl) imines and fusing point that semi-conducting resin composition of the present invention contains second-order transition temperature.
The present invention is semi-conductive resin composition, as an ion pair, can be selected from a nitrogen containing
cation, sulfonium cation, as well as containing
cation-cation in one or more of the ion pairs.
Above-mentioned ion pair preferably contains and is selected from by the positively charged ion in the positively charged ion of any expression in the formula (A)～(D) more than a kind.
Wherein, the R in the formula (A)
1The alkyl of expression carbonatoms 4 to 20 can contain heteroatoms, R
2And R
3The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different, and has at nitrogen-atoms under the situation of two keys, does not have R
3
R in the formula (B)
4The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
5, R
6And R
7The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different;
R in the formula (C)
8The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
9, R
10And R
11The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different;
X in the formula (D) representes nitrogen, sulphur or phosphorus atom, R
12, R
13, R
14And R
15The alkyl of expression carbonatoms 1 to 20 can contain heteroatoms, can be the same or different, and be under the situation of sulphur atom at X, do not have R
12
The ion-pair particularly preferably contains selected from 1 - octyl-2 - methyl pyridine
ion, one - octyl-3 - methylpyridine
ion, one - octyl-4 - methylpyridine
ion and one - octyl pyridine
ion one or more of the cation.
Embodiment
[ion pair]
The ion pair of using as conductive agent among the present invention contains as anionic two (fluorine sulphonyl) imines (following also brief note the by abridging sometimes is FSI) negatively charged ion.
The method of manufacture of FSI compound has various ways; There is not special qualification; Following method is high yield; Therefore preferred; Said method is: use nitrogenous compound basic catalysts such as (for example Trimethylamine 99s); To carry out fluorine by two (chlorine sulphonyl) imines anionic compounds that thionamic acid, chlorsulfonic acid and halogenating agent obtain and replace, obtain the FSI compound.In addition, the FSI compound that obtains through this method is a high purity, and is very good under the situation that resultant is used as conductive agent.
Further, the present invention is used in the ion pair, preferably a cationic nitrogen-containing
cation, sulfonium cation or containing
cations in any one or more kinds of ionic liquids.This ionic liquid more preferably contain any expression in the formula (A)～(D) positively charged ion more than one.Contain these cationic ionic liquids through use, obtain the better ionic liquid of conductivity.
Wherein, the R in the formula (A)
1The alkyl of expression carbonatoms 4 to 20 can contain heteroatoms, R
2And R
3The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different.But, have at nitrogen-atoms under the situation of two keys, do not have R
3
R in the formula (B)
4The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
5, R
6And R
7The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different.
R in the formula (C)
8The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
9, R
10And R
11The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms.
X in the formula (D) representes nitrogen, sulphur or phosphorus atom, R
12, R
13, R
14And R
15The alkyl of expression carbonatoms 1 to 20 can contain heteroatoms, can be the same or different.But, be under the situation of sulphur atom at X, do not have R
12
Can consider that also these positively charged ions modify with octyl group, ethylhexyl, allyl group etc.Examples of the formula (A) represented by the examples of the cation include: pyridine
cation, octyl piperidine
cation, allyl piperidine
cation, pyrrolidine
cations cations with pyrroline skeleton with pyrrole skeleton cation.Specific examples include: 1 - octyl-2 - methyl-pyridine
cation, one - octyl-3 - methylpyridine
cation, one - octyl-4 - methylpyridine
cation, one - octyl pyridine
cation, 2 - ethylhexyl pyridine
cation, one - ethyl pyridine
cation, one - butylpyridinium
cation, one - hexyl pyridine
cation, one - butyl-3 - methylpyridine
cation, one - butyl-4 - methylpyridine
cation, one - hexyl-3 - methylpyridine
cation, one - butyl -3,4 - dimethyl-pyridine
cation, 1,1 - dimethyl-pyrrolidine
cation, one - ethyl-1 - methyl pyrrolidine
cation, 1 - methyl-1 - propyl pyrrolidine
Cationic 2 - methyl-1 - pyrroline cation, 1 - ethyl-2 - phenylindole cation, 1,2 - dimethyl-indol-cation, 1 - ethylcarbazole cation.
The formula (B) represented by the examples of the cation include: imidazole
cation octylimidazolium
cation, ectoine
cation, dihydropyrimidine
cation.Specific examples include: 1,3 - dimethyl-imidazo
cation, 1,3 - diethyl imidazole
cation, 1 - ethyl-3 - methyl imidazole
cation, one - butyl - 3 - methylimidazolium
cation 1 - hexyl-3 - methyl imidazole
cation, one - octyl-3 - methyl imidazole
cation, one - decyl-3 - methyl imidazole
cation, one - Dodecyl-3 - methyl imidazole
cation, 1 - fourteen alkyl-3 - methyl imidazole
cation, 1,2 - dimethyl-3 - propyl imidazole
cation, one - ethyl -2,3 - dimethyl imidazole
cation, one - butyl-2 3 - dimethylimidazole
cation, one - hexyl -2,3 - dimethyl imidazole
cation, 1,3 - dimethyl-1 ,4,5,6 - tetrahydro-pyrimidine
cation, 1,2,3 - trimethyl -1,4,5,6 - tetrahydro-pyrimidine
cation, 1,2,3,4 - tetramethyl-1 ,4,5,6 - tetrahydro-pyrimidine
cation, 1,2,3,5 - tetramethyl -1,4,5,6 - tetrahydro-pyrimidine
cation, 1,3 - dimethyl -1,4 - dihydro-pyrimidine
cation, 1,3 - dimethyl -1,6 - dihydro-pyrimidine
cation , 1,2,3 - trimethyl -1,4 - dihydro-pyrimidine
cation, 1,2,3 - trimethyl -1,6 - dihydro-pyrimidine
cation, 1,2,3,4 - tetramethyl- -1,4 - dihydro-pyrimidine
cation, 1,2,3,4 - tetramethyl -1,6 - dihydro-pyrimidine
cation.
The formula (C) shows examples of cations include: pyrazolo
cation, two hydrogenated pyrazole
cation.Specific examples include: 1 - methyl-pyrazol-
cation 3 - methylpyrazole
cation, one - ethyl-2 - methyl-dihydro-pyrazolo
cation.
The formula (D) shows examples of cations include: tetra-alkyl ammonium cation, a trialkyl sulfonium cation, tetra-alkyl
cations, and a portion of the substituted alkyl alkenyl or alkoxy group, and an epoxy group The cation.
Specific examples include: tetramethylammonium cation, tetraethylammonium cation, tetrabutylammonium cation, tetrahexylammonium cation, triethyl-ammonium cation, tributyl ethyl ammonium cation, a trimethyl decyl yl ammonium cation, N, N-diethyl-N-methyl-N-(2 - methoxyethyl) ammonium cation, a glycidyl trimethyl ammonium cation, N, N-dimethyl-N, N-dipropyl ammonium cation, N, N-dimethyl-N, N-dihexyl ammonium cation, N, N-dipropyl-N, N-dihexyl ammonium cation, trimethylsulfonium cation, triethylammonium sulfonium cation, tributyl sulfonium cation, a trihexyl sulfonium cation, a diethyl methyl sulfonium cation, a dibutyl ethyl sulfonium cation, a dimethyl decyl sulfonium cation, tetramethylammonium
cations, tetraethyl
cation, four butyl
cation, four hexyl
cation, triethylmethylammonium
cation, tri-butyl ethyl
cation, trimethyl decyl
cationic diallyl dimethyl ammonium cation, ammonium cation benzalkonium.
Among them, methyl triethyl ammonium cation, tributyl ethyl ammonium cation, trimethyl decyl ammonium cation, N, N-diethyl-N-methyl-N-(2 - methoxy-ethyl yl) ammonium cation, a glycidyl trimethyl ammonium cation, N, N-dimethyl-N-ethyl-N-propyl ammonium cation, N, N-dimethyl-N-ethyl-N-butyl yl ammonium cation, N, N-dimethyl-N-ethyl-N-pentyl ammonium cation, N, N-dimethyl-N-ethyl-N-hexyl ammonium cation, N, N-dimethyl- -N-ethyl-N-heptyl ammonium cation, N, N-dimethyl-N-ethyl-N-nonyl ammonium cation, N, N-dimethyl-N-propyl-N-butyl- ammonium cation, N, N-dimethyl-N-propyl-N-pentyl ammonium cation, N, N-dimethyl-N-propyl-N-hexyl ammonium cation, N, N-dimethyl - N-propyl-N-heptyl ammonium cation, N, N-dimethyl-N-butyl-N-hexyl ammonium cation, N, N-dimethyl-N-butyl-N-heptyl ammonium cation , N, N-dimethyl-N-pentyl-N-hexyl ammonium cation, a trimethyl heptyl ammonium cation, N, N-diethyl-N-methyl-N-propyl ammonium cation, N, N-diethyl-N-methyl-N-pentyl ammonium cation, N, N-diethyl-N-methyl-N-heptyl ammonium cation, N, N-diethyl-N-propyl- -N-pentyl ammonium cation, triethyl-ammonium cation, triethyl propyl ammonium cation, a triethyl pentyl ammonium cation, a triethyl heptyl ammonium cation, N, N-dipropyl-N- methyl-N-ethyl ammonium cation, N, N-dipropyl-N-methyl-N-pentyl ammonium cation, N, N-dipropyl-N-butyl-N-hexyl ammonium cation, N , N-dibutyl-N-methyl-N-pentyl ammonium cation, N, N-dibutyl-N-methyl-N-hexyl ammonium cation, a trioctyl methyl ammonium cation, N-methyl- -N-ethyl-N-propyl-N-pentyl ammonium cation of asymmetric tetraalkyl ammonium cation, a diethyl methyl sulfonium cation, a dibutyl ethyl sulfonium cation, a dimethyl decyl sulfonium cation other trialkyl sulfonium cation, triethylmethylammonium
cation, tri-butyl ethyl
cation, trimethyl decyl
cations asymmetric tetraalkyl
cation.
Above-mentioned ion pair can be used a kind separately, perhaps also can mix and use more than 2 kinds.In addition, employed ion pair is can Visual Confirmation be the ion pair of liquid under 20 ℃.Among the present invention, through use fusing point be below 20 ℃ ion pair, be to be the ion pair of liquid under the normal temperature, when mixing, can mix easily and equably with matrix resin.
Need to prove that above-mentioned ionic liquid plasma also can be synthetic through known method to using commercially available ion pair.As long as it is right that synthesis method can obtain object ion, then there is not special qualification, as an example, can enumerate: halogenide method, hydroxide process, acid esters method, complex formation and neutralisation etc.
The use level of ion pair changes according to employed matrix resin and ion liquid intermiscibility, therefore, cannot treat different things as the same; Usually with respect to matrix resin 100 weight parts; Be preferably 0.01～40 weight part, more preferably 0.03～20 weight part most preferably is 0.05～10 weight part.When being lower than 0.01 weight part, can not obtain sufficient conductivity, when surpassing 40 weight parts, have the tendency that the pollution on the adherend increases.
[matrix resin]
About matrix resin,, can use the matrix resin that in the past used in the target purposes of the present invention so long as the monomeric second-order transition temperature of matrix resin is to get final product more than-100 ℃ and below 45 ℃ unqualifiedly.Second-order transition temperature can be through determination of viscoelasticity the maximum value of tan δ try to achieve.Second-order transition temperature is suitably set according to the position of using matrix resin.When second-order transition temperature surpassed 45 ℃, the cured article hardening by resin combination obtains did not demonstrate elasticity, in addition, is difficult to obtain desired electroconductibility yet.
As the preferred example of matrix resin, can enumerate: contain with in the acrylate of alkyl and/or the methacrylic ester with carbonatoms 1～14 more than a kind or 2 kinds as the matrix resin of the acrylic polymers of principal constituent.
Particularly, can enumerate: make the such monomer homopolymerization of (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) Bing Xisuandingzhi, (methyl) 2-EHA, vinylbenzene, (methyl) benzyl acrylate, (methyl) vinylformic acid 2-hydroxy methacrylate, (methyl) vinylformic acid, (methyl) propyl acrylate, dimethyl (methyl) acrylamide, isodecyl (methyl) acrylamide, decyl (methyl) propylene ester, or combination is polymerized more than 2 kinds polymkeric substance in second-order transition temperature be the polymkeric substance below 45 ℃.In the commercially available goods, for example be preferably the グ ィ カ ラ ッ Network of Daido Chemical Corp's manufacturing and the ァ Network ト Off ロ first-class that Soken Chemical & Engineering Co., Ltd. makes.
In addition, also can enumerate: the carbamate resins of a liquid type or binary liquid shape, can carry out that second-order transition temperature is the resin below 45 ℃ in polymeric acrylic resin or the Resins, epoxy etc. through thermopolymerization or radioactive rays polymerization.
As above-mentioned radioactive rays, for example can enumerate: ultraviolet ray, laser beam, alpha-ray, β ray, gamma-rays, x ray, electron rays etc.Need to prove, under the situation of using ultraviolet ray as radioactive rays, add Photoepolymerizationinitiater initiater.Photoepolymerizationinitiater initiater can be to generate free radical or cationic material thus according to the kind of radioactive rays reactive ingredients can become the introduction (drawing gold) of this polyreaction through irradiation the ultraviolet ray of suitable wavelength.
As the optical free radical polymerization starter, for example can enumerate: bitter almond oil camphor, benzoin methyl ether, bitter almond oil camphor ethyl ether, o-benzoyl yl benzoic acid methyl-to bitter almond oil camphor classes such as bitter almond oil camphor ethyl ether, bitter almond oil camphor isopropyl ether, Alpha-Methyl bitter almond oil camphors; Benzyl dimethyl ketal, Trichloroacetophenon, 2, acetophenones such as 2-diethoxy acetophenone, 1-hydroxycyclohexylphenylketone; 2-hydroxy-2-methyl Propiophenone, 2-hydroxyl-4-sec.-propyl-phenylpropyl alcohol ketones such as 2-methyl phenyl ketone; UVNUL MS-40, methyldiphenyl ketone, to chlorobenzophenone, to benzophenones such as dimethylamino UVNUL MS-40; Thioxanthene ketones such as 2-clopenthixal ketone, 2-ethyl thioxanthone, 2-isopropyl thioxanthone; Two (2,4, the 6-trimethylbenzoyl)-phenylphosphine oxide, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, (2,4, the 6-trimethylbenzoyl)-(oxyethyl group)-acylphosphine oxide classes such as phenylphosphine oxide; Benzyl, dibenzosuberone, α-acyl group oxime ester etc.
As the cationic photopolymerization initiator, for example, include: aromatic diazonium salts, aromatic iodide
salts, aromatic sulfonium salt
salt, and iron - allene complexes, cyclopentadienyl titanium complex, aryl silanol - aluminum complex organic metal complex, nitrobenzyl ester, sulfonic acid derivatives, phosphate esters, sulfonic acid derivatives, phosphate esters, phenol sulfonic acid esters, diazonaphthoquinone, N-hydroxysuccinimide imide sulfonate.About above-mentioned Photoepolymerizationinitiater initiater, also can be also with more than 2 kinds.
Photoepolymerizationinitiater initiater with respect to acrylic polymers 100 weight parts, cooperates in the scope of 0.1～10 weight part, preferred 0.2～7 weight part usually.
Also can further and with photopolymerization such as amines cause auxiliary agent.Cause auxiliary agent as photopolymerization, can enumerate: 2-dimethyl aminoethyl benzoic ether, dimethylamino benzoylformaldoxime, ESCAROL 507 ethyl ester, ESCAROL 507 isopentyl ester etc.Photopolymerization causes auxiliary agent also can be also with more than 2 kinds.Photopolymerization causes auxiliary agent, preferably in the scope of 0.05～10 weight part, further preferred 0.1～7 weight part, cooperates with respect to acrylic polymers 100 weight parts.
[preparation of semi-conducting resin composition]
Semi-conducting resin composition of the present invention obtains through in above-mentioned matrix resin, cooperating the ion pair of specified amount and utilizing ordinary method to mix.
In the semi-conducting resin composition of the present invention, except above-mentioned polymerization starter and polymerization initiation auxiliary agent, can also add diluting solvent, lubricant, homogenize agent, weighting agent etc. as required.
Semi-conducting resin composition of the present invention because conductive agent be liquid at normal temperatures, can mix in resin easily and equably, therefore, uses said composition, obtains the moulding article such as semi-conductivity resilient roller of the even and stabilization of on whole resistance value.
And easily control is according to the addition of conductive agent and therefore fixed resistance value, positively obtains having the semi-conducting resin composition of desired resistance value.
Embodiment
Below, the present invention is illustrated more specifically that the present invention is not limited to following embodiment through embodiment.
1. synthetic < the urethane acrylate A>of urethane acrylate
Under 70～80 ℃ condition, make isophorone diisocyanate (IPDI) 444g (2 moles) and 3-methyl isophthalic acid; The polyester glycol of 5-pentanediol/hexanodioic acid/terephthalic acid (1 mole) 1000g reaction; Make remaining isocyanate concentration reach specified amount; Afterwards; Add 2-hydroxyethylmethacry,ate (HEA) (2 moles) 232g and Hydroquinone monomethylether 0.8g; 70～80 ℃ of reactions down, remaining isocyanate concentration is reached below the 0.1 weight %.
<urethane acrylate B～G >
Each composition that will be used to react changes to the compound shown in the table 1, and in addition, cooperation ratio and reaction conditions that makes each composition etc. is identical with the synthesis method of urethane acrylate A, synthesis of carbamates acrylate B～G.
2. the preparation of semi-conducting resin composition
In by the above-mentioned urethane acrylate A～G that obtains, cooperate the ionic liquid shown in the table 1 with the ratio shown in the table 1 (weight part) respectively, mix, obtain semi-conducting resin composition.
Table 1
* 1: goods name: Network ラ Port one Le P-1011 (the Network ラ ィ of Co., Ltd.), MW=1000
* 2: goods name: PEG-1000, MW=1000
* 3: goods name: PPG-1000, MW=1000
* 4: goods name: PBG-1000, MW=1000
* 5: goods name: BPX-1000 (the ァ デ カ of Co., Ltd.), MW=1000
* 6: goods name: Network ラ Port one Le P-1020 (the Network ラ ィ of Co., Ltd.), MW=1000
3. the evaluation of semi-conducting resin composition
Through high pressure mercury vapour lamp 200mJ/cm
2Uviolizing, make by the above-mentioned semi-conducting resin composition that obtains and be solidified into the membranaceous of the about 100 μ m of thickness, measure tensile strength, elongation, Young's modulus, second-order transition temperature, volume resistance through following method, condition respectively.The result is shown in table 2.
< tensile strength, elongation, Young's modulus >
The TENSILON that uses the ォ リ エ of Co., Ltd. Application テ ッ Network to make; Under the condition of 20 ℃ of temperature, draw speed 50mm/ minute; Degree of stretching (elongation) when measuring maximum stress (tensile strength), fracture is by stress-stretch the slope at the initial stage of the line of writing music to obtain modulus in tension.
< second-order transition temperature >
The Rheogel-E4000 that uses the ュ of Co., Ltd. one PVC one エ system to make under the condition of 2 ℃/minute of heat-up rates, frequency 10Hz, is obtained by the maximum value of tan δ.
< volume resistance condition determination >
The R8340A high resistance analyser (ULTRA HIGH RESISTANCE METER) that uses the ァ of Co., Ltd. De バ Application テ ス ト to make is measured under the condition of 20 ℃ of temperature, humidity 65%.
Table 2
Can know by the result shown in the table 2, compare, obtain desired elasticity, electroconductibility through embodiment with the comparative example 1,2 that uses second-order transition temperature to surpass 45 ℃ resin.
Semi-conducting resin composition of the present invention can suitably be used to make the rubber-like moulding article such as charged roller, developer roll, transfer roll, fixing roller of duplicating machine etc.
The present invention at length and with reference to specific embodiment is described, only otherwise break away from the spirit and scope of the present invention, then can carry out various changes and correction, this it will be apparent to those skilled in the art that.
The Japanese patent application that the application submitted to based on November 18th, 2010 (special hope 2010-257736), its content is herein incorporated by reference.
Claims (4)
1. a semi-conducting resin composition is characterized in that, contains: second-order transition temperature is that resin and the negatively charged ion below 45 ℃ is that two (fluorine sulphonyl) imines and fusing point are the ion pair below 20 ℃.
(2) as claimed in claim 1, wherein the semiconductive resin composition, wherein said ion is selected from nitrogen-containing
cation, sulfonium cations and containing
cations cations one or more types.
3. semi-conducting resin composition as claimed in claim 2 is characterized in that, said ion pair contains and is selected from by the positively charged ion in the positively charged ion of any expression in the formula (A)～(D) more than a kind,
Wherein, the R in the formula (A)
1The alkyl of expression carbonatoms 4 to 20 can contain heteroatoms, R
2And R
3The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different, but has under the situation of two keys at nitrogen-atoms, does not have R
3
R in the formula (B)
4The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
5, R
6And R
7The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different;
R in the formula (C)
8The alkyl of expression carbonatoms 2 to 20 can contain heteroatoms, R
9, R
10And R
11The alkyl of expression hydrogen or carbonatoms 1 to 16 can contain heteroatoms, can be the same or different;
X in the formula (D) representes nitrogen, sulphur or phosphorus atom, R
12, R
13, R
14And R
15The alkyl of expression carbonatoms 1 to 20 can contain heteroatoms, can be the same or different, and be under the situation of sulphur atom at X, do not have R
12
4 as claimed in claim 3, wherein the semi-conductive resin composition, wherein said ions selected from the group comprising 1 - octyl-2 - methyl-pyridine
ion, one - octyl-3 - methylpyridine
ions, 1 - octyl-4 - methyl-pyridine
ion and one - octyl pyridine
ions in more than one kind of cation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-257736 | 2010-11-18 | ||
| JP2010257736A JP5468525B2 (en) | 2010-11-18 | 2010-11-18 | Semiconductive resin composition |
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| CN102532866B CN102532866B (en) | 2014-07-30 |
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| CN201110368778.4A Active CN102532866B (en) | 2010-11-18 | 2011-11-17 | Semi-conductive resin composition |
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| JP (1) | JP5468525B2 (en) |
| CN (1) | CN102532866B (en) |
| TW (1) | TWI450920B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107885060A (en) * | 2016-09-30 | 2018-04-06 | 柯尼卡美能达株式会社 | The manufacture method of intermediate transfer belt, image processing system and intermediate transfer belt |
| CN110753883A (en) * | 2017-06-29 | 2020-02-04 | 住友理工株式会社 | Charging member for electrophotographic apparatus |
| US11267707B2 (en) | 2019-04-16 | 2022-03-08 | Honeywell International Inc | Purification of bis(fluorosulfonyl) imide |
| CN115298645A (en) * | 2020-08-25 | 2022-11-04 | 株式会社和冠 | Covering film for pen sensor and pen sensor |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6302799B2 (en) * | 2014-08-29 | 2018-03-28 | 株式会社ブリヂストン | Conductive member, conductive roller, and image forming apparatus |
| EP3341798B1 (en) | 2016-01-27 | 2019-08-21 | Hewlett-Packard Development Company, L.P. | Liquid electrophotographic ink developer unit |
| WO2017131666A1 (en) | 2016-01-27 | 2017-08-03 | Hewlett-Packard Development Company, L.P. | Liquid electrophotographic ink developer unit |
| JP6718506B2 (en) * | 2016-01-27 | 2020-07-08 | ヒューレット−パッカード デベロップメント カンパニー エル．ピー．Ｈｅｗｌｅｔｔ‐Ｐａｃｋａｒｄ Ｄｅｖｅｌｏｐｍｅｎｔ Ｃｏｍｐａｎｙ， Ｌ．Ｐ． | Conductive roller |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101889065A (en) * | 2007-12-27 | 2010-11-17 | 赛登化学株式会社 | Adhesive composition, adhesive article, adhesive composition for optical use, and adhesion method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5305312B2 (en) * | 2007-01-04 | 2013-10-02 | 日本カーリット株式会社 | Conductivity imparting agent and conductive material |
| JP5187808B2 (en) * | 2007-01-04 | 2013-04-24 | 日本カーリット株式会社 | Conductivity imparting agent and conductive material |
| JP2009167362A (en) * | 2008-01-21 | 2009-07-30 | Sanyo Chem Ind Ltd | Microwave polymerizable composition |
| JP2010121114A (en) * | 2008-10-22 | 2010-06-03 | Mitsubishi Materials Corp | Conductive coating film-forming agent, method for producing the same, and molded article using the method |
-
2010
- 2010-11-18 JP JP2010257736A patent/JP5468525B2/en active Active
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2011
- 2011-11-11 TW TW100141284A patent/TWI450920B/en active
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101889065A (en) * | 2007-12-27 | 2010-11-17 | 赛登化学株式会社 | Adhesive composition, adhesive article, adhesive composition for optical use, and adhesion method |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107885060A (en) * | 2016-09-30 | 2018-04-06 | 柯尼卡美能达株式会社 | The manufacture method of intermediate transfer belt, image processing system and intermediate transfer belt |
| CN110753883A (en) * | 2017-06-29 | 2020-02-04 | 住友理工株式会社 | Charging member for electrophotographic apparatus |
| US11267707B2 (en) | 2019-04-16 | 2022-03-08 | Honeywell International Inc | Purification of bis(fluorosulfonyl) imide |
| CN115298645A (en) * | 2020-08-25 | 2022-11-04 | 株式会社和冠 | Covering film for pen sensor and pen sensor |
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| Publication number | Publication date |
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| TWI450920B (en) | 2014-09-01 |
| JP2012107134A (en) | 2012-06-07 |
| TW201221568A (en) | 2012-06-01 |
| CN102532866B (en) | 2014-07-30 |
| JP5468525B2 (en) | 2014-04-09 |
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