JP2018041048A - Triboelectrifying member - Google Patents
Triboelectrifying member Download PDFInfo
- Publication number
- JP2018041048A JP2018041048A JP2016177010A JP2016177010A JP2018041048A JP 2018041048 A JP2018041048 A JP 2018041048A JP 2016177010 A JP2016177010 A JP 2016177010A JP 2016177010 A JP2016177010 A JP 2016177010A JP 2018041048 A JP2018041048 A JP 2018041048A
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- Prior art keywords
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- charge imparting
- substituted
- resin
- toner
- Prior art date
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- -1 benz imidazolinone compound Chemical class 0.000 claims abstract description 40
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 18
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 230000000694 effects Effects 0.000 abstract description 11
- 229920005989 resin Polymers 0.000 description 33
- 239000011347 resin Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 18
- 238000005259 measurement Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 7
- 235000013980 iron oxide Nutrition 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910000859 α-Fe Inorganic materials 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000005493 quinolyl group Chemical group 0.000 description 5
- 239000002344 surface layer Substances 0.000 description 5
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZXXRHVCYZYWAHI-UHFFFAOYSA-N 2-amino-2,3-dihydrobenzimidazol-5-one Chemical compound O=C1C=CC2=NC(N)NC2=C1 ZXXRHVCYZYWAHI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910001308 Zinc ferrite Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052742 iron 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
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- KOFUWGOMTZTSTO-UHFFFAOYSA-N 3-amino-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(N)C2=C1 KOFUWGOMTZTSTO-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910016516 CuFe2O4 Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910001289 Manganese-zinc ferrite Inorganic materials 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910003264 NiFe2O4 Inorganic materials 0.000 description 1
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- 239000004677 Nylon Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 229910009493 Y3Fe5O12 Inorganic materials 0.000 description 1
- JHNCXGXWSIOXSX-UHFFFAOYSA-N [Nd+3].[O-2].[Fe+2] Chemical compound [Nd+3].[O-2].[Fe+2] JHNCXGXWSIOXSX-UHFFFAOYSA-N 0.000 description 1
- JIYIUPFAJUGHNL-UHFFFAOYSA-N [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Mn++].[Mn++].[Mn++].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Zn++].[Zn++] Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Mn++].[Mn++].[Mn++].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Zn++].[Zn++] JIYIUPFAJUGHNL-UHFFFAOYSA-N 0.000 description 1
- GZHZIMFFZGAOGY-UHFFFAOYSA-N [O-2].[Fe+2].[La+3] Chemical compound [O-2].[Fe+2].[La+3] GZHZIMFFZGAOGY-UHFFFAOYSA-N 0.000 description 1
- WQHONKDTTOGZPR-UHFFFAOYSA-N [O-2].[O-2].[Mn+2].[Fe+2] Chemical compound [O-2].[O-2].[Mn+2].[Fe+2] WQHONKDTTOGZPR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
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- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- BAXLMRUQFAMMQC-UHFFFAOYSA-N cadmium(2+) iron(2+) oxygen(2-) Chemical compound [Cd+2].[O-2].[Fe+2].[O-2] BAXLMRUQFAMMQC-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- DXKGMXNZSJMWAF-UHFFFAOYSA-N copper;oxido(oxo)iron Chemical compound [Cu+2].[O-][Fe]=O.[O-][Fe]=O DXKGMXNZSJMWAF-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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Landscapes
- Dry Development In Electrophotography (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
本発明は、電子写真、静電記録などにおいて静電潜像を現像するために用いられる現像剤（トナー）に対し、キャリアや現像スリーブの如き現像剤担持体、ドクターブレードの如き現像剤層厚規制部材等の摩擦帯電付与部材に関する。 The present invention relates to a developer (toner) used for developing an electrostatic latent image in electrophotography, electrostatic recording, etc., with respect to a developer carrier such as a carrier and a developing sleeve, and a developer layer thickness such as a doctor blade. The present invention relates to a frictional charge imparting member such as a regulating member.
電子写真方式による画像形成プロセスでは、無機または有機材料からなる感光体に静電潜像を形成し、これをトナーにより現像、紙やプラスチックフィルム等に転写、定着して可視潜像を得る。感光体にはその構成により正帯電性と負帯電性があり、露光により印字部を静電荷像として残す場合は逆符号帯電性トナーにより現像する。トナーに電荷を保持させる方法としては、トナー結着樹脂の摩擦帯電性を利用する方法、トナーに電荷制御剤を添加する方法が一般的である。 In an electrophotographic image forming process, an electrostatic latent image is formed on a photosensitive member made of an inorganic or organic material, and this is developed with toner, transferred and fixed on paper, plastic film, or the like to obtain a visible latent image. The photosensitive member has a positive charging property and a negative charging property depending on its configuration. When the printed part is left as an electrostatic charge image by exposure, the photosensitive member is developed with a reverse sign charging toner. As a method for holding the charge in the toner, a method utilizing the triboelectric charging property of the toner binder resin and a method of adding a charge control agent to the toner are generally used.
トナーの結着樹脂の摩擦帯電性を利用してトナーの電荷を保持する方法の場合は、結着樹脂に要求される特性としては十分な摩擦帯電性、定着工程における耐オフセット性及び定着性を同時に満たすことが要求される。しかしながら、一般的に定着性の良い結着樹脂は、摩擦帯電特性が劣る傾向がある。近年、低エネルギーでトナーを定着させる方法として、結着樹脂のガラス転移点（Ｔｇ）や結着樹脂の中の低分子量の樹脂の割合を増やす方法があるが、このような樹脂においても、摩擦帯電性が劣る傾向があった。 In the case of a method for retaining the charge of the toner by utilizing the triboelectric charging property of the toner binder resin, the characteristics required for the binder resin are sufficient triboelectric chargeability, anti-offset property and fixing property in the fixing process. It is required to charge at the same time. However, generally binder resins with good fixability tend to be inferior in tribocharging properties. In recent years, as a method for fixing toner with low energy, there is a method of increasing the glass transition point (T g ) of the binder resin or the ratio of the low molecular weight resin in the binder resin. There was a tendency for the triboelectric chargeability to be inferior.
一方、電荷制御剤をトナーに添加し、トナーの摩擦帯電性を向上させる方法は、トナー表層に露出した電荷制御剤がトナーから脱落または乖離し、キャリア、ドラム、ブレード、現像スリーブ、その他部材の汚染が生じる。その結果、帯電性が低下し、複写枚数の増加に従い、画像濃度の低下、再現性の低下、カブリ等の問題が生じてくる。 On the other hand, the method of adding a charge control agent to the toner to improve the triboelectric chargeability of the toner is that the charge control agent exposed on the toner surface layer falls off or separates from the toner, and the carrier, drum, blade, developing sleeve, and other members Contamination occurs. As a result, the chargeability decreases, and problems such as a decrease in image density, a decrease in reproducibility, and fogging occur as the number of copies increases.
そこで、トナーへの帯電付与を電荷制御剤や結着樹脂だけで解決するのではなく、各種部材とトナーを接触させることにより、摩擦電荷を得る方法が提案されている。主な摩擦帯電部材としては、二成分系現像剤においてはキャリアであり、一成分系現像剤供給部材、撹拌部材、搬送スクリューなどがあげられる。 Accordingly, a method has been proposed in which triboelectric charge is obtained by bringing various members into contact with the toner, instead of solving the charge imparting to the toner with only the charge control agent and the binder resin. The main frictional charging member is a carrier in a two-component developer, and examples thereof include a one-component developer supply member, a stirring member, and a conveying screw.
一成分現像剤に用いられる現像剤層厚規制部材（規制ブレード）は、トナーがブレード間を通過する際にブレードに接触することにより、トナーに摩擦帯電を付与することが知られており、ブレードとしては金属またはウレタン樹脂等のエラストマーが用いられている。正帯電特性のトナーには、主にシリコーン系のエラストマーを、負帯電特性のトナーにはナイロン系のエラストマーをトナーと接触する部材の表層に使用し、トナーに電荷を付与させる方法が知られている。 It is known that a developer layer thickness regulating member (regulating blade) used for a one-component developer imparts frictional charge to the toner by contacting the blade when the toner passes between the blades. As such, an elastomer such as metal or urethane resin is used. It is known to use a silicone-based elastomer for positively charged toners and a nylon-based elastomer for the negatively charged toners on the surface layer of the member in contact with the toner to impart charge to the toner. Yes.
また、現像スリーブにおいてもその表面にトナーを担持搬送することにより、トナーに摩擦電荷を与えることが知られており、現像スリーブの表層にトナーの摩擦電荷を与えやすい樹脂により被覆する方法も知られている。 In addition, it is known that the developing sleeve also carries a toner on the surface thereof to carry a toner, so that a triboelectric charge is given to the toner, and a method of coating the surface of the developing sleeve with a resin that easily gives the triboelectric charge of the toner is also known. ing.
上記ブレード類及び現像スリーブの表層は、樹脂で被覆されているが、トナーに摩擦電荷を与えるために、帯電性粒子をブレード等の部材の表層に分散させる方法が提案されている。 The blades and the surface layer of the developing sleeve are coated with a resin. In order to give a frictional charge to the toner, a method of dispersing chargeable particles on the surface layer of a member such as a blade has been proposed.
二成分系現像剤に用いられる摩擦帯電付与部材であるキャリアにおいては、鉄粉やフェライトが用いられていたが、近年鉄粉やフェライトを芯材として、アクリル樹脂、フッ素樹脂、シリコーン樹脂、フェノール樹脂等の樹脂で被覆したキャリアが用いられることが多くなっている。これらの樹脂被覆キャリアは、樹脂で被覆されているが、トナーに摩擦電荷を更に与えるために、キャリアの表層に帯電性粒子を分散せせる方法が提案されている。 In the carrier that is a frictional charge imparting member used in the two-component developer, iron powder or ferrite has been used. Recently, iron powder or ferrite is used as a core material, and acrylic resin, fluorine resin, silicone resin, phenol resin. In many cases, a carrier coated with a resin such as is used. Although these resin-coated carriers are coated with a resin, a method of dispersing chargeable particles on the surface layer of the carrier has been proposed in order to further impart a triboelectric charge to the toner.
特許文献1〜２には、前記ブレード、スリーブ、キャリアの表面に帯電性粒子としてフェノキシ酢酸誘導体を分散させた摩擦帯電付与部材が開示されている。しかしながら、前記フェノキシ酢酸誘導体は、高温時に昇華または、分解する傾向があり、摩擦により局所的に高温になるキャリア等の摩擦帯電付与部材として用いるには、耐熱性が要求されていた。また、摩擦帯電付与効果が不十分であり、表面に前記フェノキシ酢酸誘導体を分散させたキャリアでトナーを摩擦帯電させた二成分系のトナーおよび前記フェノキシ酢酸誘導体を表面に分散させたスリーブまたはブレードを用いて摩擦帯電させた一成分系のトナーにおいても、トナーの帯電が不十分という欠点があった。 Patent Documents 1 and 2 disclose a frictional charge imparting member in which a phenoxyacetic acid derivative is dispersed as chargeable particles on the surfaces of the blade, sleeve, and carrier. However, the phenoxyacetic acid derivative has a tendency to sublime or decompose at high temperatures, and heat resistance is required for use as a frictional charge imparting member such as a carrier that locally becomes high temperature due to friction. In addition, a two-component toner in which the effect of imparting triboelectric charge is insufficient and the toner is triboelectrically charged with a carrier in which the phenoxyacetic acid derivative is dispersed on the surface, and a sleeve or blade in which the phenoxyacetic acid derivative is dispersed on the surface. Even in the one-component toner that is friction-charged using the toner, there is a drawback that the toner is not sufficiently charged.
本発明は、電子写真、静電記録材等の分野で静電潜像を顕像化するために用いられる画像形成装置に用いられる現像剤（トナー）に対し、摩擦電荷を付与するための摩擦帯電付与部材において、優れた帯電付与効果および耐熱性がある帯電付与部材を提供することである。 The present invention relates to a friction for imparting a triboelectric charge to a developer (toner) used in an image forming apparatus used for developing an electrostatic latent image in the field of electrophotography, electrostatic recording material and the like. An object of the present invention is to provide a charge imparting member having an excellent charge imparting effect and heat resistance.
本発明は、前記目的を達成するために鋭意研究した結果、電子写真、静電記録材等の分野で静電潜像を顕像化するために用いられる画像形成装置に用いられる現像剤（トナー）に対し摩擦電荷を付与するために、ベンズイミダゾリノン誘導体を含有する摩擦帯電付与部材である。すなわち、本発明は以下のような摩擦帯電付与部材である。 According to the present invention, as a result of intensive research to achieve the above object, a developer (toner) used in an image forming apparatus used for developing an electrostatic latent image in the field of electrophotography, electrostatic recording material, and the like. ) Is a triboelectric charge imparting member containing a benzimidazolinone derivative. That is, the present invention is a frictional charge imparting member as follows.
［１］下記一般式（１）で表されるベンズイミダゾリノン化合物を有効成分として含有することを特徴とする摩擦帯電付与部材に関する。 [1] A frictional charge imparting member comprising a benzimidazolinone compound represented by the following general formula (1) as an active ingredient.
（式中、Ｒ１およびＲ２はそれぞれ独立に、水素原子、置換基を有していてもよい炭素原子数１ないし８の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の複素環基または置換もしくは無置換の縮合多環芳香族基を表すものとする。） (In the formula, R 1 and R 2 each independently have a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent, or a substituent. It represents a cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)
［２］電子写真方式に用いられる摩擦帯電付与部材である。 [2] A frictional charge imparting member used in an electrophotographic system.
［３］摩擦帯電付与部材が現像剤担持体であることを特徴とする。 [3] The triboelectric charging member is a developer carrier.
［４］摩擦帯電付与部材がキャリア粒子であることを特徴とする。 [4] The triboelectric charging member is a carrier particle.
［５］摩擦帯電付与部材が現像剤層厚規制部材であることを特徴とする。 [5] The friction charge imparting member is a developer layer thickness regulating member.
本発明の摩擦帯電付与部材は、耐熱性が良好であり、摩擦により局所的に高温になるキャリア等に摩擦帯電付与部材として用いても、十分に耐えることができる。また、本発明の摩擦帯電付与部材は、トナーを帯電させるべく要求される摩擦帯電付与効果についても十分な付与効果を有している。 The frictional charge imparting member of the present invention has good heat resistance and can sufficiently withstand even when used as a frictional charge imparting member on a carrier or the like that locally becomes high temperature due to friction. Further, the frictional charge imparting member of the present invention has a sufficient imparting effect with respect to the frictional charge imparting effect required to charge the toner.
次に好ましい実施形態を挙げて本発明をさらに詳細に説明する。 Next, the present invention will be described in more detail with reference to preferred embodiments.
本発明に使用する一般式（１）で表されるベンズイミダゾリノン化合物は、既知の方法によって製造することができる。例えば、相当アミノベンズイミダゾールと相当するイソシアネートとを、縮合することによって、本発明に使用するベンズイミダゾリノン化合物を合成することができる。 The benzimidazolinone compound represented by the general formula (1) used in the present invention can be produced by a known method. For example, the benzimidazolinone compound used in the present invention can be synthesized by condensing a corresponding aminobenzimidazole and a corresponding isocyanate.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換基を有していてもよい炭素原子数１ないし８の直鎖状もしくは分岐状のアルキル基を表すもの」における「炭素原子数１ないし８の直鎖状もしくは分岐状のアルキル基」としては、例えば、メチル基、エチル基、ｎ−プロピル基、２−プロピル基、ｎ−ブチル基、ｓｅｃ−ブチル基、２−メチルプロピル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、１−メチルブチル基、１−エチルプロピル基、１，１−ジメチルプロピル基、１，２−ジメチルプロピル基、ｎ−ヘキシル基、１−メチルペンチル基、２−メチルペンチル基、３−メチルペンチル基、４−メチルペンチル基、１−エチルブチル基、２−エチルブチル基、１，１−ジメチルブチル基、１，２−ジメチルブチル基、１，３−ジメチルブチル基、１，４−ジメチルブチル基、２，２−ジメチルブチル基、２，３−ジメチルブチル基、３，３−ジメチルブチル基、１−エチル−２−メチル−プロピル基、１，１，２−トリメチルプロピル基である。 In general formula (1), R 1 and R 2 are each independently “the number of carbon atoms” in “which represents a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent”. Examples of the 1 to 8 linear or branched alkyl group include a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, an n-butyl group, a sec-butyl group, and a 2-methylpropyl group. Tert-butyl group, n-pentyl group, 1-methylbutyl group, 1-ethylpropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, n-hexyl group, 1-methylpentyl group, 2 -Methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3 Dimethylbutyl group, 1,4-dimethylbutyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethyl-2-methyl-propyl group, 1,1 , 2-trimethylpropyl group.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換基を有していてもよい炭素原子数１ないし８の直鎖状もしくは分岐状のアルキル基を表すもの」における「置換基」としては、具体的に、フッ素原子、塩素原子、シアノ基、水酸基、ニトロ基、シクロペンチル基、シクロヘキシル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルコキシ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基で置換されたジアルキルアミノ基、炭素原子数１ないし２０の直鎖状もしくは分岐状のアシル基、炭素原子数１ないし２０の直鎖状もしくは分岐状のアルコキシカルボニル基、炭素原子数１ないし６のエポキシアルキル基、フェニル基、ナフチル基、アントリル基、フルオレニル基、スチリル基、ピリジル基、ピリドインドリル基、キノリル基、ベンゾチアゾリル基のような基をあげることができ、これらの置換基はさらに置換されていても良い。 In the general formula (1), R 1 and R 2 are each independently a “substituent” in “which represents a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent”. Specifically, fluorine atom, chlorine atom, cyano group, hydroxyl group, nitro group, cyclopentyl group, cyclohexyl group, linear or branched alkoxy group having 1 to 6 carbon atoms, 1 to 6 carbon atoms A dialkylamino group substituted by a linear or branched alkyl group, a linear or branched acyl group having 1 to 20 carbon atoms, a linear or branched alkoxy group having 1 to 20 carbon atoms Carbonyl group, epoxyalkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, anthryl group, fluorenyl group, styryl group, pyridyl group, pyridoindo Group, quinolyl group, can be mentioned groups such as benzothiazolyl group, these substituents may be further substituted.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基を表すもの」における「炭素原子数５ないし１０のシクロアルキル基」としては、例えば、シクロペンチレン基、シクロヘキシレン基、シクロヘプチレン基、シクロオクチレン基、シクロノニレン基又はシクロデシレン基である。 In general formula (1), R1 and R2 are each independently "cycloalkyl having 5 to 10 carbon atoms" in "which represents an optionally substituted cycloalkyl group having 5 to 10 carbon atoms". Examples of the “group” include a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a cyclononylene group, and a cyclodecylene group.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基を表すもの」における「置換基」として、具体的には、フッ素原子、塩素原子、シアノ基、水酸基、ニトロ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、シクロペンチル基、シクロヘキシル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルコキシ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基で置換されたジアルキルアミノ基、フェニル基、ナフチル基、アントリル基、フルオレニル基、スチリル基、ピリジル基、ピリドインドリル基、キノリル基、ベンゾチアゾリル基のような基をあげることができ、これらの置換基はさらに置換されていても良い。 In the general formula (1), R 1 and R 2 are each independently a “substituent” in “an optionally substituted cycloalkyl group having 5 to 10 carbon atoms”. , Fluorine atom, chlorine atom, cyano group, hydroxyl group, nitro group, linear or branched alkyl group having 1 to 6 carbon atoms, cyclopentyl group, cyclohexyl group, linear or branched group having 1 to 6 carbon atoms -Like alkoxy group, dialkylamino group substituted with linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, anthryl group, fluorenyl group, styryl group, pyridyl group, pyridoindolyl And a group such as a quinolyl group and a benzothiazolyl group, and these substituents may be further substituted.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換もしくは無置換の芳香族炭化水素基を表すもの」における「芳香族炭化水素基」として、例えばフェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基のような基をあげることができる。 In the general formula (1), R 1 and R 2 are each independently an “aromatic hydrocarbon group” in “representing a substituted or unsubstituted aromatic hydrocarbon group”, for example, a phenyl group, a biphenylyl group, a terphenylyl group, Examples thereof include naphthyl group, anthryl group, phenanthryl group, fluorenyl group, indenyl group and pyrenyl group.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換もしくは無置換の芳香族炭化水素基を表すもの」における「置換基」として、具体的には、フッ素原子、塩素原子、シアノ基、水酸基、ニトロ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、シクロペンチル基、シクロヘキシル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルコキシ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基で置換されたジアルキルアミノ基、フェニル基、ナフチル基、アントリル基、フルオレニル基、スチリル基、ピリジル基、ピリドインドリル基、キノリル基、ベンゾチアゾリル基のような基をあげることができ、これらの置換基はさらに置換されていても良い。 In general formula (1), R1 and R2 are each independently a “substituent” in “representing a substituted or unsubstituted aromatic hydrocarbon group”, specifically, a fluorine atom, a chlorine atom, a cyano group , Hydroxyl group, nitro group, linear or branched alkyl group having 1 to 6 carbon atoms, cyclopentyl group, cyclohexyl group, linear or branched alkoxy group having 1 to 6 carbon atoms, 1 carbon atom Or a dialkylamino group, phenyl group, naphthyl group, anthryl group, fluorenyl group, styryl group, pyridyl group, pyridoindolyl group, quinolyl group, benzothiazolyl group substituted with 6 straight or branched alkyl groups And these substituents may be further substituted.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換もしくは無置換の複素環基または置換もしくは無置換の縮合多環芳香族基を表すもの」における「複素環基」または「縮合多環芳香族基」として、例えば、ピリジル基、トリアジル基、ピリミジル基、フラニル基、ピラニル基、チオフェニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチオフェニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基のような基をあげることができる。 In general formula (1), R 1 and R 2 are each independently a “heterocyclic group” or “condensed polycyclic group” in “a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group”. Examples of the `` ring aromatic group '' include pyridyl group, triazyl group, pyrimidyl group, furanyl group, pyranyl group, thiophenyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, carbazolyl group, benzoxazolyl group. And a group such as an alkyl group, a benzothiazolyl group, a quinoxalyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a naphthyridinyl group, a phenanthrolinyl group, and an acridinyl group.
一般式（１）中、Ｒ１およびＲ２はそれぞれ独立に、「置換もしくは無置換の複素環基または置換もしくは無置換の縮合多環芳香族基を表すもの」における「置換基」として、具体的には、フッ素原子、塩素原子、シアノ基、水酸基、ニトロ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、シクロペンチル基、シクロヘキシル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルコキシ基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基で置換されたジアルキルアミノ基、フェニル基、ナフチル基、アントリル基、フルオレニル基、スチリル基、ピリジル基、ピリドインドリル基、キノリル基、ベンゾチアゾリル基、テノイル基のような基をあげることができ、これらの置換基はさらに置換されていても良い。 In the general formula (1), R1 and R2 are each independently a “substituent” in “representing a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group”. Is a fluorine atom, a chlorine atom, a cyano group, a hydroxyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, a cyclohexyl group, a straight chain having 1 to 6 carbon atoms or Branched alkoxy group, dialkylamino group substituted with linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, anthryl group, fluorenyl group, styryl group, pyridyl group, pyridoin Examples thereof include a drill group, a quinolyl group, a benzothiazolyl group, and a thenoyl group, and these substituents may be further substituted. .
本発明に使用する一般式（１）で表されるベンズイミダゾール化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。
尚、下記構造式では、水素原子は省略して記載している。
Specific examples of preferable compounds among the benzimidazole compounds represented by the general formula (1) used in the present invention are shown below, but the present invention is not limited to these compounds.
In the following structural formula, hydrogen atoms are omitted.
部材に、摩擦帯電付与性を与えるために用いる摩擦帯電付与剤は、一般式（１）で表されるベンズイミダゾリノン化合物を有効成分とするものであり、好ましくは上記例示化合物２〜１０を有効成分とするものである。 The triboelectric charge-imparting agent used for imparting triboelectric charge-providing properties to the member comprises a benzimidazolinone compound represented by the general formula (1) as an active ingredient, preferably the above exemplified compounds 2 to 10 are effective. Ingredients.
部材に摩擦帯電付与性を与えるために用いる摩擦帯電付与剤は、一般式（１）で表されるベンズイミダゾリノン化合物を有効成分とするものであり、前記一般式（１）で表される化合物を1種または2種以上併用してもよい。摩擦帯電付与性を与えるベンズイミダゾリノン化合物の融点が３００℃以上であるため、従来のフェノキシ酢酸化合物と比べて耐熱性が良い。摩擦帯電付与部材に用いた場合に、摩擦による局部的な発熱に対しても化合物が安定であり、また帯電付与効果においても優れている。 The triboelectric charge-imparting agent used for imparting triboelectric charge-providing properties to the member comprises a benzimidazolinone compound represented by the general formula (1) as an active ingredient, and the compound represented by the general formula (1) May be used alone or in combination of two or more. Since the melting point of the benzimidazolinone compound that imparts triboelectric chargeability is 300 ° C. or higher, the heat resistance is better than that of a conventional phenoxyacetic acid compound. When used in a frictional charge imparting member, the compound is stable against local heat generation due to friction, and is excellent in charge imparting effect.
また、本発明で使用するベンズイミダゾリノン化合物は、未反応の原料として少量のアミノベンズイミダゾリノンまたはイソシアネート等の物質または水分を含むことを必ずしも排除するものではない。 In addition, the benzimidazolinone compound used in the present invention does not necessarily exclude the inclusion of a small amount of a substance such as aminobenzimidazolinone or isocyanate or moisture as an unreacted raw material.
前記一般式（１）で表される化合物を部材の表面に含有させる方法については、特に限定されない。例えば、摩擦帯電付与部材の基材に、一般式（１）で表されるベンズイミダゾリノン化合物を含有する塗布液を、ディッピング法、スプレー法、コーティング法などの方法で塗布し乾燥させれば、本発明の摩擦帯電付与部材が得られる。 The method for containing the compound represented by the general formula (1) on the surface of the member is not particularly limited. For example, if the coating liquid containing the benzimidazolinone compound represented by the general formula (1) is applied to the base material of the triboelectric charging member by a method such as dipping, spraying, or coating, and dried, The frictional charge imparting member of the present invention is obtained.
一般式（１）で表されるベンズイミダゾリノン化合物を含有する塗布液を調整する際に使用する溶剤としては、トルエン系、キシレン系、アルコール系、エステル系、エーテル系、グリコールエーテル系、ケトン系、炭化水素類（脂肪族）、炭化水素類（芳香族）、などが挙げられる。更に具体的に例を挙げると、エステル系には酢酸エチル、酢酸ブチルなどがあり、ケトン系にはアセトン、メチルエチルケトンなどがあり、アルコール系にはエタノール、メタノール、ブタノール、イソプロピルアルコールなどがあり、炭化水素類（脂肪族）にはミネラルスピリット、炭化水素類（芳香族）にはトルエン、キシレンなどがある。 Solvents used in preparing the coating solution containing the benzimidazolinone compound represented by the general formula (1) include toluene, xylene, alcohol, ester, ether, glycol ether, and ketone. , Hydrocarbons (aliphatic), hydrocarbons (aromatic), and the like. More specifically, ester type includes ethyl acetate, butyl acetate, etc., ketone type includes acetone, methyl ethyl ketone, etc., alcohol type includes ethanol, methanol, butanol, isopropyl alcohol, etc. Hydrogen (aliphatic) includes mineral spirit, and hydrocarbons (aromatic) include toluene and xylene.
または、一般式（１）で表されるベンズイミダゾリノン化合物を樹脂に分散させ、摩擦帯電付与部材の基材に公知の方法で被覆させる方法等があげられる。 Alternatively, there may be mentioned a method in which the benzimidazolinone compound represented by the general formula (1) is dispersed in a resin and the base material of the frictional charge imparting member is coated by a known method.
さらに、成形可能な樹脂中に、一般式（１）で表されるベンズイミダゾリノン化合物を公知の方法で分散含有させた後、スリーブ、ドクターブレード等に成形することにより製造することもできる。 Further, the benzimidazolinone compound represented by the general formula (1) can be dispersed and contained in a moldable resin by a known method, and then molded into a sleeve, a doctor blade, or the like.
前記記載の被覆させるために使用する樹脂またはスリーブ等の摩擦帯電付与部材の基材として成形可能な樹脂としては、一般に公知の樹脂が使用可能である。例えば、スチレン系樹脂、ビニル系樹脂、アクリル系樹脂、エポキシ系樹脂、ポリエステル系樹脂、ポリエーテルスルホン系樹脂、ポリカーボネート系樹脂、ポリフェニレンオキサイド系樹脂、ポリアミド系樹脂、フッ素系樹脂、アルキレッド樹脂、フェノール樹脂、メラミン樹脂、ポリイミド樹脂、尿素樹脂、シリコーン樹脂、ポリウレタン樹脂等の熱可塑性樹脂、または光硬化性樹脂等を使用することができる。 As a resin that can be used for coating as described above or a resin that can be molded as a base material of a frictional charge imparting member such as a sleeve, generally known resins can be used. For example, styrene resin, vinyl resin, acrylic resin, epoxy resin, polyester resin, polyethersulfone resin, polycarbonate resin, polyphenylene oxide resin, polyamide resin, fluorine resin, alkyl red resin, phenol A thermoplastic resin such as a resin, a melamine resin, a polyimide resin, a urea resin, a silicone resin, or a polyurethane resin, or a photocurable resin can be used.
一般式（１）で表されるベンズイミダゾリノン化合物を樹脂に分散させる割合は、樹脂１００質量部に対して、１〜８０質量部が好ましい、１〜２０質量部がより好ましい、１〜５質量部が特に好ましい。１質量部未満では添加による帯電付与性の向上が見られにくく、８０質量部を超えると被膜強度が低下する傾向にある。 The proportion of the benzimidazolinone compound represented by the general formula (1) dispersed in the resin is preferably 1 to 80 parts by weight, more preferably 1 to 20 parts by weight, with respect to 100 parts by weight of the resin. Part is particularly preferred. If the amount is less than 1 part by mass, the charge imparting property is hardly improved by addition, and if it exceeds 80 parts by mass, the coating strength tends to decrease.
本発明において、上記摩擦帯電付与剤は体積平均粒径を０．１〜２０μｍの範囲内に調整して用いるのが好ましく、０．１〜１０μｍの範囲内に調整して用いるのが特に好ましい。前記体積平均粒径が０．１μｍより小さいと、部材表面に出現する帯電付与剤が極めて少なくなり目的の電荷制御効果が得られなくなり、また２０μｍより大きいと、部材から欠落する帯電付与剤が増加し、機内汚染などの悪影響が出るため好ましくない。 In the present invention, the triboelectric charge-imparting agent is preferably used by adjusting the volume average particle diameter within the range of 0.1 to 20 μm, and particularly preferably adjusted within the range of 0.1 to 10 μm. If the volume average particle size is smaller than 0.1 μm, the charge imparting agent appearing on the surface of the member is extremely small and the desired charge control effect cannot be obtained, and if it is larger than 20 μm, the charge imparting agent missing from the member is increased. However, it is not preferable because of adverse effects such as in-flight contamination.
一般式（１）で表されるベンズイミダゾリノン化合物を樹脂に均一分散させるには、摩擦帯電付与剤の粒度分布はシャープであることは好適である。つまり、摩擦帯電付与剤の大きさを揃えながら上記の体積平均粒径まで調整することが好ましい。具体的に粒度分布におけるＤ９０／Ｄ１０が４．０以下であることは好ましい。なお、Ｄ１０、Ｄ９０はそれぞれ、粒子径の分布を測定することによって得られる値である。Ｄ１０とは体積基準での１０％積算粒径、Ｄ９０とは体積基準での９０％積算粒径であることを意味する。これらの値は、上記体積平均粒径と同様の方法（レーザー回折／散乱式粒度分布測定）によって測定された値である。上記Ｄ９０／Ｄ１０は、３．５以下であることがより好ましい。 In order to uniformly disperse the benzimidazolinone compound represented by the general formula (1) in the resin, it is preferable that the particle size distribution of the triboelectric charge imparting agent is sharp. That is, it is preferable to adjust to the volume average particle size while adjusting the size of the frictional charge imparting agent. Specifically, it is preferable that D 90 / D 10 in the particle size distribution is 4.0 or less. D 10 and D 90 are values obtained by measuring the particle size distribution. 10% cumulative particle diameter on a volume basis and D 10, which means that the D 90 is 90% cumulative particle diameter on a volume basis. These values are values measured by the same method (laser diffraction / scattering particle size distribution measurement) as the volume average particle size. The D 90 / D 10 is more preferably 3.5 or less.
本発明に使用するキャリア用の芯材は、特に限定はなく、例えば、（１）マグネタイト、マグヘマイト、フェライトの如き磁性酸化鉄、および他の金属酸化物を含む酸化鉄。または、（２）鉄、コバルト、ニッケルのような金属、あるいは、これらの眷属とアルミニウム、コバルト、銅、鉛、マグネシウム、スズ、亜鉛、アンチモン、ベリリウム、ビスマス、カルシウム、マンガン、セレン、チタン、タングステン、バナジウムのような金属との合金。（３）およびこれらの混合物等が用いられる。（４）さらには、ガラス、炭化ケイ素などンセラミック粒子、樹脂紛体、磁性体を含有する樹脂紛体などがあげられる。 The carrier core material used in the present invention is not particularly limited. For example, (1) iron oxide containing magnetic iron oxide such as magnetite, maghemite, and ferrite, and other metal oxides. Or (2) metals such as iron, cobalt, nickel, or their metals and aluminum, cobalt, copper, lead, magnesium, tin, zinc, antimony, beryllium, bismuth, calcium, manganese, selenium, titanium, tungsten , Alloys with metals like vanadium. (3) and mixtures thereof are used. (4) Further, examples thereof include ceramic particles such as glass and silicon carbide, resin powder, and resin powder containing a magnetic material.
磁性酸化鉄として具体的に例示すると、四三酸化鉄（Ｆｅ３Ｏ４）、三二酸化鉄（γ−Ｆｅ２Ｏ３）、酸化鉄亜鉛（ＺｎＦｅ２Ｏ４）、酸化鉄イットリウム（Ｙ３Ｆｅ５Ｏ１２）、酸化鉄カドミウム（ＣｄＦｅ２Ｏ４）、酸化鉄ガドニウム（Ｇｄ３Ｆｅ２Ｏ４）、酸化鉄銅（ＣｕＦｅ２Ｏ４）、酸化鉄鉛（ＰｂＦｅ２Ｏ４）、酸化鉄ニッケル（ＮｉＦｅ２Ｏ４）、酸化鉄ネオジム（ＮｄＦｅ２Ｏ４）、酸化鉄バリウム（ＢａＦｅ２Ｏ４）、酸化鉄マグネシウム（ＭｇＦｅ２Ｏ４）、酸化鉄マンガン（ＭｎＦｅ２Ｏ４）、酸化鉄ランタン（ＬａＦｅ２Ｏ４）等が挙げられる。 Specific examples of magnetic iron oxide include iron trioxide (Fe3O4), iron sesquioxide (γ-Fe2O3), zinc oxide (ZnFe2O4), iron yttrium oxide (Y3Fe5O12), iron cadmium oxide (CdFe2O4), iron oxide Gadonium (Gd3Fe2O4), iron oxide copper (CuFe2O4), iron oxide lead (PbFe2O4), iron oxide nickel (NiFe2O4), iron oxide neodymium (NdFe2O4), iron barium oxide (BaFe2O4), iron magnesium oxide (MgFe2O4), iron oxide manganese (MnFe2O4), iron lanthanum oxide (LaFe2O4) and the like.
また、異種元素を含有するマグネタイト、マグヘマイト、フェライト等の生磁性酸化鉄およびその混合物も使用できる。例示すると、異種元素としては、リチウム、ベリリウム、ボロン、マグネシウム、アルミニウム、シリコン、リン、ゲルマニウム、ジルコニウム、スズ、イオウ、カルシウム、スカンジウム、チタン、バナジウム、クロム、マンガン、コバルト、ニッケル、銅、亜鉛、ガリウム等が挙げられる。具体的には、マンガン−亜鉛系フェライト、ニッケル−亜鉛系フェライト、マンガン−マグネシウム系フェライトおよびリチウム系フェライト、銅−亜鉛系フェライト等が挙げられる。 Moreover, biomagnetic iron oxides such as magnetite, maghemite, and ferrite containing different elements and mixtures thereof can be used. Illustrative examples of the different elements include lithium, beryllium, boron, magnesium, aluminum, silicon, phosphorus, germanium, zirconium, tin, sulfur, calcium, scandium, titanium, vanadium, chromium, manganese, cobalt, nickel, copper, zinc, Examples include gallium. Specific examples include manganese-zinc ferrite, nickel-zinc ferrite, manganese-magnesium ferrite, lithium ferrite, and copper-zinc ferrite.
異種元素としては、マグネシウム、アルミニウム、シリコン、リン、ジルコニウムが好ましく、これらは、酸化鉄結晶格子の中に取り込まれていても良いし、酸化物として酸化鉄中に取り込まれていても良いし、表面に酸化物あるいは水酸化物として存在していても良い。 As the heterogeneous elements, magnesium, aluminum, silicon, phosphorus, and zirconium are preferable, and these may be incorporated into the iron oxide crystal lattice, or may be incorporated into the iron oxide as an oxide, It may exist on the surface as an oxide or hydroxide.
本発明に使用できる現像層厚規制部材の基材は、特に制限はなく、例えば、鉄、ステンレス、ニッケル、アルミニウムなどン金属あるいは合金、およびセラミックス、プラスチックス、ゴムなどの非金属材料などを用い、これらの材料を板状に加工して用いる場合が多いが、ロール形状としても良い。また、金属の基材にゴム板を貼り付けて用いたり、金属の弾性板スリーブと接触する部分にエラストマー材を貼り付けて用いたりもできる。 The substrate of the development layer thickness regulating member that can be used in the present invention is not particularly limited, and for example, a metal or alloy such as iron, stainless steel, nickel, or aluminum, and a non-metallic material such as ceramics, plastics, or rubber is used. In many cases, these materials are processed into a plate shape and used, but a roll shape may be used. Further, a rubber plate can be attached to a metal base material, or an elastomer material can be attached to a portion in contact with the metal elastic plate sleeve.
以下、実施例をもって本発明を説明するが、これらは本発明をなんら制限するものではない。実施例において、「部」は全て「質量部」を表す。 EXAMPLES Hereinafter, although an Example demonstrates this invention, these do not limit this invention at all. In the examples, all “parts” represent “parts by mass”.
本発明に用いられる一般式（１）で表されるベンズイミダゾリノン化合物の精製はカラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土などによる吸着精製、溶媒による再結晶や晶析法などによって行った。化合物の同定は、ＮＭＲ分析によって行なった。 The benzimidazolinone compound represented by the general formula (1) used in the present invention was purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., solvent recrystallization or crystallization. . The compound was identified by NMR analysis.
［合成例１（例示化合物Ｎｏ．３の合成）］
窒素置換した反応容器に、６．２６部の２−アミノ−５−ベンズイミダゾリノン、５．３３部の４−メチルフェニルイソシアネート、１８９部のＤＭＦ（Ｎ，Ｎ−ジメチルホルムアミド）を加え、撹拌した。攪拌しながら、３０℃で４時間、７０℃で３時間反応させた。室温まで冷却し、析出した結晶をろ過によって採取した後、メタノールで洗浄を行って、類白色結晶１１．０部(収率９７％)を得た。
[Synthesis Example 1 (Synthesis of Exemplified Compound No. 3)]
6.26 parts of 2-amino-5-benzimidazolinone, 5.33 parts of 4-methylphenyl isocyanate, 189 parts of DMF (N, N-dimethylformamide) were added to a nitrogen-substituted reaction vessel and stirred. . While stirring, the reaction was carried out at 30 ° C. for 4 hours and at 70 ° C. for 3 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with methanol to obtain 11.0 parts of white crystals (yield 97%).
得られた類白色結晶についてＮＭＲを使用して構造を同定した。１Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６）の測定結果は、２．２３ｐｐｍ（３Ｈ）、６．７９ｐｐｍ（２Ｈ）、７．０７ｐｐｍ（２Ｈ）、７．３２ｐｐｍ（３Ｈ）、８．４５ｐｐｍ（２Ｈ）、１０．４２ｐｐｍ（１Ｈ）、１０．５２ｐｐｍ（１Ｈ）であり、得られた類白色結晶は例示化合物Ｎｏ．３であった。 The structure of the obtained white crystals was identified using NMR. The measurement results of 1H-NMR (DMSO-d 6 ) are 2.23 ppm (3H), 6.79 ppm (2H), 7.07 ppm (2H), 7.32 ppm (3H), 8.45 ppm (2H), 10 .42 ppm (1H) and 10.52 ppm (1H). 3.
［合成例２（例示化合物Ｎｏ．４の合成）］
窒素置換した反応容器に、２−アミノ−５−ベンズイミダゾリノン ６．２６部、シクロヘキシルイソシアネート ５．０１部、ＤＭＦ １８９部を加え、撹拌した。攪拌しながら、３０℃で３．５時間、７０℃で４時間反応させた。室温まで冷却し、析出した結晶をろ過によって採取した後、メタノールで洗浄を行って、白色結晶１０．７部(収率９８％)を得た。
[Synthesis Example 2 (Synthesis of Exemplified Compound No. 4)]
To a reaction vessel purged with nitrogen, 6.26 parts of 2-amino-5-benzimidazolinone, 5.01 parts of cyclohexyl isocyanate, and 189 parts of DMF were added and stirred. While stirring, the reaction was carried out at 30 ° C. for 3.5 hours and at 70 ° C. for 4 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with methanol to obtain 10.7 parts (yield 98%) of white crystals.
得られた白色結晶についてＮＭＲを使用して構造を同定した。１Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６）の測定結果は、１．１６ｐｐｍ（３Ｈ）、１．３０ｐｐｍ（２Ｈ）、１．５３ｐｐｍ（１Ｈ）、１．６５ｐｐｍ（２Ｈ）、１．７９ｐｐｍ（２Ｈ）、３．４４ｐｐｍ（１Ｈ）、５．９１ｐｐｍ（１Ｈ）、６．６６−６．７１ｐｐｍ（１Ｈ）、６．７５ｐｐｍ（１Ｈ）、７．２７ｐｐｍ（１Ｈ）、８．１０ｐｐｍ（1Ｈ）、１０．３３ｐｐｍ（１Ｈ）、１０．４２ｐｐｍ（１Ｈ）であり、得られた白色結晶は例示化合物Ｎｏ．４であった。 The structure of the white crystals obtained was identified using NMR. The measurement results of 1H-NMR (DMSO-d 6 ) are 1.16 ppm (3H), 1.30 ppm (2H), 1.53 ppm (1H), 1.65 ppm (2H), 1.79 ppm (2H), 3 .44 ppm (1H), 5.91 ppm (1H), 6.66-6.71 ppm (1H), 6.75 ppm (1H), 7.27 ppm (1H), 8.10 ppm (1H), 10.33 ppm (1H) ), 10.42 ppm (1H), and the obtained white crystals are exemplified compound Nos. 4.
［合成例３（例示化合物Ｎｏ．５の合成）］
窒素置換した反応容器に、２−アミノ−５−ベンズイミダゾリノン ６．２６部、トリレン−２，４−ジイソシアネート ３．４８部、ＤＭＦ １８９部を加え、撹拌した。攪拌しながら、３０℃で４時間、７０℃で３．５時間反応させた。室温まで冷却し、析出した結晶をろ過によって採取した後、メタノールで洗浄を行って、薄紫色結晶５．１部(収率５４％)を得た。
[Synthesis Example 3 (Synthesis of Exemplified Compound No. 5)]
To a reaction vessel purged with nitrogen, 6.26 parts of 2-amino-5-benzimidazolinone, 3.48 parts of tolylene-2,4-diisocyanate and 189 parts of DMF were added and stirred. While stirring, the reaction was carried out at 30 ° C. for 4 hours and at 70 ° C. for 3.5 hours. After cooling to room temperature, the precipitated crystals were collected by filtration and washed with methanol to obtain 5.1 parts (yield 54%) of pale purple crystals.
得られた薄紫結晶についてＮＭＲを使用して構造を同定した。１Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６）の測定結果は、２．１８ｐｐｍ（３Ｈ）、６．８２ｐｐｍ（４Ｈ）、７．０４ｐｐｍ（１Ｈ）、７．１７ｐｐｍ（１Ｈ）、７．３５ｐｐｍ（１Ｈ）、７．４０ｐｐｍ（１Ｈ）、７．７８ｐｐｍ（１Ｈ）、７．９６ｐｐｍ（１Ｈ）、８．３６ｐｐｍ（1Ｈ）、８．５３ｐｐｍ（１Ｈ）、８．９１ｐｐｍ（１Ｈ）、１０．４４ｐｐｍ（２Ｈ）、１０．５５ｐｐｍ（２Ｈ）であり、得られた薄紫結晶は例示化合物Ｎｏ．５であった。 The structure of the obtained light purple crystal was identified using NMR. The measurement results of 1H-NMR (DMSO-d 6 ) are 2.18 ppm (3H), 6.82 ppm (4H), 7.04 ppm (1H), 7.17 ppm (1H), 7.35 ppm (1H), 7 .40 ppm (1H), 7.78 ppm (1H), 7.96 ppm (1H), 8.36 ppm (1H), 8.53 ppm (1H), 8.91 ppm (1H), 10.44 ppm (2H), 10. 55 ppm (2H), and the resulting light purple crystals were exemplified by Compound No. It was 5.
［帯電付与部材の帯電量測定］
［実施例１］
合成例１で得られた化合物を、シリコンコート系のフェライトキャリア（パウダーテック株式会社製、Ｆ９６−１５０）１００部に対して０．５部の割合で混合して振とうし、合成例１で得られた化合物（例示化合物Ｎｏ．３）を帯電させる。を帯電させた後、ブローオフ帯電量測定機（東芝ケミカル社製、ＴＢ−２００型）を用いて、温度２５℃、湿度５０％の雰囲気下（ＮＮ環境下）における飽和帯電量の測定を行った。また、ノンコートキャリア（（パウダーテック株式会社製、Ｆ−１５０）についても同様の測定を行った。帯電量測定結果を表１に示す。
[Measurement of charge amount of electrifying member]
[Example 1]
The compound obtained in Synthesis Example 1 was mixed and shaken at a ratio of 0.5 part with respect to 100 parts of a silicon-coated ferrite carrier (F96-150, manufactured by Powder Tech Co., Ltd.). The obtained compound (Exemplary Compound No. 3) is charged. Then, using a blow-off charge measuring machine (Toshiba Chemical Co., Ltd., TB-200 type), the saturation charge amount was measured in an atmosphere (temperature of 25 ° C. and humidity of 50% (under NN environment)). . Moreover, the same measurement was performed also about the non-coating carrier (Powder Tech Co., Ltd., F-150).
［実施例２］
実施例１の合成例１で得られた化合物を、合成例２で得られた化合物に変更した以外は同様の測定を行った。帯電量測定結果を表１に示す。
[Example 2]
The same measurement was performed except that the compound obtained in Synthesis Example 1 of Example 1 was changed to the compound obtained in Synthesis Example 2. The charge amount measurement results are shown in Table 1.
［実施例３］
［ポリエステル樹脂トナーの作製及び帯電量の測定］
［母体トナーの製造：粉砕法］
スチレン−アクリレート系共重合体樹脂（三井化学株式会社製、ＣＰＲ−１００）９５部と、カーボンブラック（三菱化学株式会社製、ＭＡ−１００）５部とを、１１０℃の加熱混合装置によって溶融混合した。得られた混合物を室温まで冷却した後、ハンマーミルを用いて粗粉砕した。さらに、ジェットミルで微粉砕した後、分級し、レーザー回析・散乱法測定（マイクロトラック粒度分布測定装置）で測定した体積基準の平均粒径が１０±０．５μｍの母体粉砕トナーを得た。
[Example 3]
[Production of polyester resin toner and measurement of charge amount]
[Manufacture of base toner: grinding method]
Melting and mixing 95 parts of styrene-acrylate copolymer resin (CPR-100, manufactured by Mitsui Chemicals, Inc.) and 5 parts of carbon black (MA-100, manufactured by Mitsubishi Chemical Corporation) using a heating and mixing device at 110 ° C. did. The resulting mixture was cooled to room temperature and then coarsely pulverized using a hammer mill. Furthermore, after finely pulverizing with a jet mill, classification was performed, and a base pulverized toner having a volume-based average particle size of 10 ± 0.5 μm measured by laser diffraction / scattering method measurement (microtrack particle size distribution measuring device) was obtained. .
［電荷付与部材外添型トナーの製造］
前記記載の母体トナー１００部にたいして合成実施例１で得られた化合部０．５部をビーカー中で混合した。混合したサンプルを、ポットミル（協立理工社製SK-M10型）に投入し、メモリ７０で、１秒（時間）×２０回（回数）で間欠運転させて、電荷付与部材外添型トナーを製造した。
[Manufacture of externally added charge imparting member toner]
To 100 parts of the base toner described above, 0.5 part of the combined part obtained in Synthesis Example 1 was mixed in a beaker. The mixed sample is put into a pot mill (SK-M10 type manufactured by Kyoritsu Riko Co., Ltd.), and intermittently operated in the memory 70 for 1 second (time) × 20 times (number of times). Manufactured.
［帯電量の測定］
前記で得られた電荷付与部材外添型トナーを、シリコンコート系のフェライトキャリア（パウダーテック株式会社製、Ｆ９６−１５０）１００部に対して４部の割合で混合して振とうし、トナーを帯電させた後、ブローオフ帯電量測定機（東芝ケミカル社製、ＴＢ−２００型）を用いて、温度２５℃、湿度５０％の雰囲気下（ＮＮ環境下）における飽和帯電量の測定を行った。帯電量測定結果を表２に示す。
[Measurement of charge amount]
The externally added charge imparting member toner obtained above was mixed and shaken at a ratio of 4 parts to 100 parts of a silicon-coated ferrite carrier (F96-150, manufactured by Powder Tech Co., Ltd.) After charging, the saturation charge amount in an atmosphere (temperature of 25 ° C. and humidity 50% (under NN environment)) was measured using a blow-off charge amount measuring machine (Toshiba Chemical Co., Ltd., TB-200 type). The charge amount measurement results are shown in Table 2.
［比較例１］
実施例３に合成例１で得られた化合物を使用しない以外は、同様の測定を行った。帯電量測定結果を表２に示す。
[Comparative Example 1]
The same measurement was performed except that the compound obtained in Synthesis Example 1 was not used in Example 3. The charge amount measurement results are shown in Table 2.
表２の摩擦帯電評価の結果から、合成したベンズイミダゾリノン化合物によりトナーの摩擦帯電付与効果は高いポジ帯電性を示した。ポリエステル樹脂に外添してトナー評価した結果、ネガ性の樹脂をポジ帯電へと制御することができた。また、ベンズイミダゾリノン化合物は３００℃以上の高い融点を有しており、耐熱性にも優れている。よって、本発明に用いられる一般式（１）で表されるベンズイミダゾリノン化合物は摩擦帯電付与剤として摩擦帯電付与部材に確実に有用である。 From the results of the triboelectric evaluation shown in Table 2, the synthesized benzimidazolinone compound showed a high positive chargeability in the effect of imparting triboelectric charge to the toner. As a result of externally adding to the polyester resin and evaluating the toner, the negative resin could be controlled to be positively charged. Further, the benzimidazolinone compound has a high melting point of 300 ° C. or higher, and is excellent in heat resistance. Therefore, the benzimidazolinone compound represented by the general formula (1) used in the present invention is certainly useful as a friction charge imparting agent for a friction charge imparting member.
本発明に係る一般式（１）で表されるベンズイミダゾリノン化合物を含有する摩擦帯電付与部材は、耐熱性が良好であり、摩擦により局所的に高温になるキャリア等に摩擦帯電付与部材として用いても、十分に耐えることができる。また、本発明の摩擦帯電付与部材は、トナーを帯電させるべく要求される摩擦帯電付与効果についても十分な付与効果を有している。従って、電子写真、静電記録材等の分野で静電潜像を顕像化するために用いられる画像形成装置に用いられる現像剤（トナー）に対し、摩擦電荷を付与するための摩擦帯電付与部材として好適である。 The frictional charge imparting member containing the benzimidazolinone compound represented by the general formula (1) according to the present invention has good heat resistance and is used as a frictional charge imparting member for a carrier or the like that locally becomes high due to friction. Even withstand enough. Further, the frictional charge imparting member of the present invention has a sufficient imparting effect with respect to the frictional charge imparting effect required to charge the toner. Therefore, triboelectric charge application for applying triboelectric charge to a developer (toner) used in an image forming apparatus used for developing an electrostatic latent image in the field of electrophotography, electrostatic recording material, etc. It is suitable as a member.
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| US11125997B2 (en) | 2017-11-10 | 2021-09-21 | Sony Interactive Entertainment Inc. | Information processing apparatus, information processing method, and program |
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