JP2009198987A - トナー - Google Patents
トナー Download PDFInfo
- Publication number
- JP2009198987A JP2009198987A JP2008043079A JP2008043079A JP2009198987A JP 2009198987 A JP2009198987 A JP 2009198987A JP 2008043079 A JP2008043079 A JP 2008043079A JP 2008043079 A JP2008043079 A JP 2008043079A JP 2009198987 A JP2009198987 A JP 2009198987A
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- Prior art keywords
- resin
- core
- toner
- intermediate layer
- resin constituting
- 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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- 229920005989 resin Polymers 0.000 claims abstract description 201
- 239000011347 resin Substances 0.000 claims abstract description 201
- 239000007771 core particle Substances 0.000 claims abstract description 102
- 239000002245 particle Substances 0.000 claims abstract description 98
- 230000009477 glass transition Effects 0.000 claims abstract description 64
- 239000000463 material Substances 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims description 85
- 239000010419 fine particle Substances 0.000 claims description 79
- 239000004645 polyester resin Substances 0.000 claims description 36
- 229920001225 polyester resin Polymers 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 239000012736 aqueous medium Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 19
- 239000000470 constituent Substances 0.000 claims description 18
- 239000003086 colorant Substances 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000005227 gel permeation chromatography Methods 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 abstract description 17
- 239000002775 capsule Substances 0.000 abstract description 7
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- 238000003786 synthesis reaction Methods 0.000 description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 44
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- 239000003505 polymerization initiator Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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- 239000003381 stabilizer Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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- 239000001993 wax Substances 0.000 description 15
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 14
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 239000011230 binding agent Substances 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 230000001771 impaired effect Effects 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
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- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical compound CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000004945 emulsification Methods 0.000 description 6
- 239000006247 magnetic powder Substances 0.000 description 6
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- 239000002243 precursor Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000001506 calcium phosphate Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 4
- 229940078499 tricalcium phosphate Drugs 0.000 description 4
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 4
- 235000019731 tricalcium phosphate Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 3
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 238000005338 heat storage Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 239000007869 azo polymerization initiator Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
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- 230000001186 cumulative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940067741 sodium octyl sulfate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
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- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- SMECTXYFLVLAJE-UHFFFAOYSA-M sodium;pentadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCOS([O-])(=O)=O SMECTXYFLVLAJE-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- ZUSDEBDNDIJDMZ-UHFFFAOYSA-N tert-butyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(C)(C)C ZUSDEBDNDIJDMZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- MXHBQKVKHGQWRB-UHFFFAOYSA-N trihexyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C(C(=O)OCCCCCC)=C1 MXHBQKVKHGQWRB-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229940077935 zinc phosphate Drugs 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
【解決手段】 懸濁重合法によって得られる芯粒子と、該芯粒子の表面に樹脂微粒子を固着させて形成した外殻から構成されるカプセル構造を有するトナーにおいて、前記芯粒子を、コアと該コアの表面を被覆するように設けた中間層とで構成し、さらに、前記コアと前記中間層と前記外殻の構成材料を、それぞれの樹脂のガラス転移温度並びに重量平均分子量が特定の関係となるように組み合わせる。
【選択図】なし
Description
装置:HLC−8120GPC(東ソー製)
カラム:KF801,802,803,804,805,806,807(Shodex製)
カラム温度:40℃
solv.:THF
酸価(mgKOH/g)={(S−B)×0.1f×56.1}/W
(ポリエステル樹脂の作製)
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に下記の単量体を仕込み、エステル化触媒としてテトラブトキシチタネート0.03質量部を添加し、窒素雰囲気下、温度220℃に昇温して、撹拌しながら5時間反応を行った。
ビスフェノールA−プロピレンオキサイド2モル付加物:49.6質量部
エチレングリコール:8.9質量部
テレフタル酸:22.4質量部
イソフタル酸:15.2質量部
5−ナトリウムスルホイソフタル酸:3.9質量部
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に、得られたポリエステル樹脂100.0質量部とメチルエチルケトン45.0質量部、テトラヒドロフラン45.0質量部を仕込み、温度80℃に加熱して溶解した。
(ポリエステル樹脂の作製)
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に下記の単量体を仕込み、エステル化触媒としてテトラブトキシチタネート0.03質量部を添加し、窒素雰囲気下、温度220℃に昇温して、撹拌しながら5時間反応を行った。
ビスフェノールA−プロピレンオキサイド2モル付加物:50.0質量部
エチレングリコール:9.0質量部
テレフタル酸:21.1質量部
イソフタル酸:14.3質量部
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に、得られたポリエステル樹脂100.0質量部とブチルセロソルブ75.0質量部を仕込み、温度90℃に加熱して溶解した後、70℃まで冷却した。
合成例1において、単量体の仕込み量を下記のように変更した以外は、合成例1と同様にしてポリエステル樹脂の水分散体を得た。これを、樹脂微粒子分散液(c)とした。
ビスフェノールA−プロピレンオキサイド2モル付加物:63.0質量部
エチレングリコール:7.6質量部
テレフタル酸:12.7質量部
イソフタル酸:12.7質量部
フマル酸:9.1質量部
5−ナトリウムスルホイソフタル酸:4.1質量部
(スチレン/アクリル系樹脂の作製)
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器にメチルエチルケトン100.0質量部を仕込み、窒素雰囲気下、温度80℃に昇温した。次いで、下記の単量体からなる混合物に重合開始剤としてt−ブチルパーオキシ−2−エチルヘキサノエート3.0質量部を添加し、撹拌しながら2時間かけて滴下した。
スチレン:94.2質量部
メチルメタクリレート:2.4質量部
メタクリル酸:3.3質量部
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に、メチルエチルケトン150.0質量部を仕込み、上記スチレン/アクリル系樹脂100.0質量部を加えて溶解した。
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に、イオン交換水350.0質量部とドデシルベンゼンスルホン酸ナトリウム0.5質量部を仕込み、窒素雰囲気下、温度90℃に昇温した。次に、2%過酸化水素水溶液8質量部、および2%アスコルビン酸水溶液8質量部を添加した。
スチレン:75.2質量部
n−ブチルアクリレート:22.8質量部
アクリル酸:2.0質量部
t−ドデシルメルカプタン:0.05質量部
ドデシルベンゼンスルホン酸ナトリウム:0.3質量部
ポリオキシエチレンノニルフェニルエーテル:0.01質量部
イオン交換水:20.0質量部
2%過酸化水素水溶液:40質量部
2%アスコルビン酸水溶液:40質量部
合成例5において、単量体混合物を下記のように変更した以外は、合成例5と同様にしてスチレン/アクリル系樹脂の水分散体を得た。これを、樹脂微粒子分散液(f)とした。
スチレン:95.9質量部
メチルメタクリレート:2.3質量部
アクリル酸:1.8質量部
t−ドデシルメルカプタン:0.05質量部
撹拌機、コンデンサー、温度計、窒素導入管を備えた反応容器に下記の単量体を仕込み、エステル化触媒としてジブチル錫オキサイド0.05質量部を添加し、窒素雰囲気下、温度220℃に昇温した。撹拌しながら、且つ生成するメタノールを留去しながら5時間反応を行った。
ビスフェノールA−プロピレンオキサイド2モル付加物:69.6質量部
テレフタル酸:21.7質量部
無水トリメリット酸:8.7質量部
合成例7において、単量体の仕込み量を下記のように変更した以外は、合成例7と同様にして反応を行い、ポリエステル樹脂を得た。これを、中間層形成用樹脂(B)とした。
ビスフェノールA−プロピレンオキサイド2モル付加物:69.9質量部
テレフタル酸:24.3質量部
無水トリメリット酸:5.8質量部
合成例7において、スチレン30.0質量部を、スチレン23.4質量部とn−ブチルアクリレート6.6質量部に変えた以外は合成例7と同様にして、スチレンとn−ブチルアクリレートで変性されたポリエステル樹脂を得た。これを、中間層形成用樹脂(C)とした。
合成例7において、スチレン30.0質量部を、スチレン15.0質量部とn−ブチルアクリレート15.0質量部に変えた以外は合成例7と同様にして、スチレンとn−ブチルアクリレートで変性されたポリエステル樹脂を得た。これを、中間層形成用樹脂(D)とした。
合成例7において、前駆体樹脂(1)を合成する際の反応条件と、スチレン変性する際の反応条件を調整して、高分子量化したスチレン変性ポリエステル樹脂を得た。これを、中間層形成用樹脂(E)とした。
合成例7において、単量体の仕込み量を下記のように変更し、合成例7と同様の方法で反応を行って得られた前駆体樹脂を使用した以外は合成例7と同様にして、酸価を持たないスチレン変性ポリエステル樹脂を得た。これを、中間層形成用樹脂(F)とした。
ビスフェノールA−プロピレンオキシド2モル付加物:71.3質量部
テレフタル酸:28.7質量部
(顔料分散ペーストの作製)
スチレン:212.9質量部
Cuフタロシアニン(Pigment Blue 15:3):19.7質量部
イオン交換水1152.0質量部に0.1モル/リットル−Na3PO4水溶液390.0質量部を投入し、クレアミックス(エム・テクニック社製)を用いて撹拌しながら、温度60℃に加温した。1.0モル/リットル−CaCl2水溶液58.0質量部を添加してさらに撹拌を続け、Ca3(PO4)2からなる分散安定剤を含む水系媒体を調製した。
n−ブチルアクリレート:114.7質量部
中間層形成用樹脂(A):20.0質量部
合成例13において、中間層形成用樹脂(A)20.0質量部を、3.9質量部に変えた以外は合成例13と同様にして、芯粒子分散液(A2)を作製した。
合成例13において、中間層形成用樹脂(A)20.0質量部を、42.3質量部に変えた以外は合成例13と同様にして、芯粒子分散液(A3)を作製した。
合成例13において、中間層形成用樹脂(A)に代えて、中間層形成用樹脂(B)乃至(F)をそれぞれ用いた以外は合成例13と同様にして、芯粒子分散液(B)乃至(F)を作製した。
合成例13において、中間層形成用樹脂(A)を用いなかった以外は合成例13と同様の方法で重合を行った。
(トナー粒子の作製)
合成例13で得られた芯粒子分散液(A1)500.0質量部(固形分100.0質量部)に、撹拌下、合成例1で得られた微粒子分散液(a)25.0質量部(固形分5.0質量部)を添加し、30分間撹拌を続けた後、温度55℃に昇温した。
シリカ微粉体100質量部を、10質量部のヘキサメチルジシラザンで処理し、さらに10質量部のシリコーンオイルで処理して、一次粒径12nm、BET比表面積が120m2/gの疎水性シリカ微粉体を調製した。次いで、上記トナー粒子100.0質量部に対して、該疎水性シリカ微粉体1.0質量部を加え、ヘンシェルミキサー(三井三池化工機製)を用いて混合した。こうして、本発明のトナーを作製した。
実施例1において、微粒子分散液(a)に代えて、微粒子分散液(b)を用いた以外は実施例1と同様にして、本発明のトナーを作製した。
実施例1において、芯粒子分散液(A1)に代えて、芯粒子分散液(B)を用いた以外は実施例1と同様にして、本発明のトナーを作製した。
(トナー粒子の作製)
イオン交換水380.0質量部に、合成例5で得られた微粒子分散液(e)25.0質量部(固形分5.0質量部)を加え、撹拌しながら、合成例21で得られた芯粒子(G)100.0質量部を徐々に添加して均一に分散させた。
次いで、得られた分散液を冷却し、ろ過し、水洗および乾燥してトナー粒子を得た。
得られたトナー粒子に、実施例1と同様の方法で疎水性シリカ微粉体を外添して、比較例のトナーを作製した。
(顔料分散ペーストの作製)
スチレン:187.0質量部
Cuフタロシアニン(Pigment Blue 15:3):19.6質量部
上記材料を容器中で十分プレミックスした後、これを温度20℃以下に保ったままアトライター(三井三池化工機製)を用いて約4時間均一に分散混合し、顔料分散ペーストを作製した。
イオン交換水1152.0質量部に0.1モル/リットル−Na3PO4水溶液390.0質量部を投入し、撹拌しながら温度60℃に加温した。1.0モル/リットル−CaCl2水溶液58.0質量部を添加してさらに撹拌を続け、Ca3(PO4)2からなる分散安定剤を含む水系媒体を調製した。
n−ブチルアクリレート:100.5質量部
中間層形成用樹脂(A):60.0質量部
荷電制御剤(BONTRON E−84(オリエント化学社)):3.3質量部
さらに、得られた懸濁液を、パドル撹拌翼で撹拌しつつ、温度60℃にて10時間重合を行った。
得られたトナー粒子に、実施例1と同様の方法で疎水性シリカ微粉体を外添して、比較例のトナーを作製した。
(トナー粒子の作製)
イオン交換水360.0質量部に、合成例5で得られた微粒子分散液(e)25.0質量部と合成例6で得られた微粒子分散液(f)25.0質量部(いずれも固形分5.0質量部)を加えた。次に、撹拌しながら、合成例21で得られた芯粒子(G)100.0質量部を徐々に添加して均一に分散させた。
得られたトナー粒子に、実施例1と同様の方法で疎水性シリカ微粉体を外添して、比較例のトナーを作製した。
(トナー粒子の作製)
イオン交換水380.0質量部に、合成例5で得られた微粒子分散液(e)25.0質量部(固形分5.0質量部)を加え、撹拌しながら、合成例21で得られた芯粒子(G)100.0質量部を徐々に添加して均一に分散させた。
得られたトナー粒子に、実施例1と同様の方法で疎水性シリカ微粉体を外添して、比較例のトナーを作製した。
トナー10gを容積100mlのポリカップに量り採り、これを内部温度50℃の恒温槽に入れて7日間放置する。その後、ポリカップを取り出して、中のトナーの状態変化を目視にて評価する。判定基準は以下の通りである。
A:変化なし
B:凝集体があるが、すぐにほぐれる
C:凝集体がやや多く、ほぐれにくい
D:凝集体が多く、容易にはほぐれない
E:全くほぐれない
トナーと、シリコーン樹脂で表面被覆した磁性微粒子分散型樹脂キャリア(平均粒径35μm)を、トナー濃度が7.0質量%になるように混合して二成分現像剤を調製する。
実施例1において、使用する芯粒子分散液と微粒子分散液を、表5に示す組み合わせに変えた以外は実施例1と同様にして、本発明のトナーおよび比較例のトナーをそれぞれ作製した。
実施例1において、芯粒子分散液(A1)に代えて、芯粒子分散液(A2)を用いた以外は実施例1と同様にして、本発明のトナーを作製した。
実施例1において、芯粒子分散液(A1)に代えて、芯粒子分散液(A3)を用いた以外は実施例1と同様にして、本発明のトナーを作製した。
実施例1において、微粒子分散液(a)の添加量を10.0質量部(固形分2.0質量部)に変えた以外は実施例1と同様にして、本発明のトナーを作製した。
実施例1において、微粒子分散液(a)の添加量を15.0質量部(固形分3.0質量部)に変えた以外は実施例1と同様にして、本発明のトナーを作製した。
Claims (14)
- 少なくとも重合性単量体と着色剤と該重合性単量体に溶解する樹脂を含有する重合性単量体組成物を水系媒体中に分散させ、該重合性単量体を重合して得られる芯粒子と、該芯粒子の表面に樹脂微粒子を固着させて形成した外殻から構成されるトナー粒子を有するトナーであって、
該芯粒子が、コアと該コアの表面を被覆してなる中間層を有し、
該コアが、前記重合性単量体を主構成材料とする重合体から形成されたものであり、
該中間層が、前記重合性単量体組成物中に予め溶解させた前記樹脂が重合時に芯粒子の表面部に偏析して形成されたものであり、
前記中間層を構成する樹脂のガラス転移温度、および、前記外殻を構成する樹脂のガラス転移温度は、前記コアを構成する樹脂のガラス転移温度よりも高く、
且つ、前記中間層を構成する樹脂の重量平均分子量、および、前記外殻を構成する樹脂の重量平均分子量は、前記コアを構成する樹脂の重量平均分子量よりも小さいことを特徴とするトナー。 - 前記コアを構成する樹脂のガラス転移温度が20乃至60℃であり、且つ、前記中間層を構成する樹脂と前記コアを構成する樹脂のガラス転移温度の差、および、前記外殻を構成する樹脂と前記コアを構成する樹脂のガラス転移温度の差が、それぞれ15乃至50℃の範囲であることを特徴とする請求項1に記載のトナー。
- 前記中間層を構成する樹脂のガラス転移温度は、前記外殻を構成する樹脂のガラス転移温度よりも高いことを特徴とする請求項2に記載のトナー。
- 前記コアを構成する樹脂は、ゲルパーミエーションクロマトグラフィー(GPC)測定による重量平均分子量が10000乃至100000であることを特徴とする請求項1乃至3のいずれかに記載のトナー。
- 前記中間層を構成する樹脂の重量平均分子量は、前記外殻を構成する樹脂の重量平均分子量よりも小さいことを特徴とする請求項4に記載のトナー。
- 前記外殻を構成する樹脂微粒子が、カルボキシル基および/または、スルホン酸基を有する自己水分散型の樹脂微粒子で構成されることを特徴とする請求項1乃至5に記載のトナー。
- 前記樹脂微粒子を構成する樹脂の酸価が、5.0乃至40.0mgKOH/gであることを特徴とする請求項6に記載のトナー。
- 前記樹脂微粒子を構成する樹脂が、ポリエステル樹脂からなることを特徴とする請求項6又は7に記載のトナー。
- 前記中間層を構成する樹脂が、前記重合性単量体には可溶で、且つ該重合性単量体からなる重合体に対しては完全に相溶しない樹脂からなることを特徴とする請求項1乃至8のいずれかに記載のトナー。
- 前記中間層を構成する樹脂が、ポリエステル樹脂またはビニル系単量体で変性されたビニル変性ポリエステル樹脂からなることを特徴とする請求項9に記載のトナー。
- 前記中間層を構成する樹脂が、ビニル系単量体で変性されたビニル変性ポリエステル樹脂からなることを特徴とする請求項10に記載のトナー。
- 前記中間層を構成する樹脂の酸価が、1.0乃至30.0mgKOH/gであることを特徴とする請求項9乃至11のいずれかに記載のトナー。
- 前記芯粒子に占める前記中間層の割合が、質量比で1乃至10%であることを特徴とする請求項1乃至12のいずれかに記載のトナー。
- 前記外殻が、前記芯粒子の表面を90%以上被覆していることを特徴とする請求項1乃至13のいずれかに記載のトナー。
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JP2010139696A (ja) * | 2008-12-11 | 2010-06-24 | Canon Inc | トナー及びトナーの製造方法 |
JP2010145555A (ja) * | 2008-12-16 | 2010-07-01 | Canon Inc | トナーおよびトナーの製造方法 |
JP2013033233A (ja) * | 2011-06-28 | 2013-02-14 | Konica Minolta Business Technologies Inc | 静電荷像現像用トナー及び静電荷像現像用トナーの製造方法 |
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JP2015152818A (ja) * | 2014-02-17 | 2015-08-24 | キヤノン株式会社 | トナーの製造方法 |
JP2015219289A (ja) * | 2014-05-14 | 2015-12-07 | キヤノン株式会社 | トナー粒子の製造方法およびトナーの製造方法 |
JP2015232706A (ja) * | 2014-05-14 | 2015-12-24 | キヤノン株式会社 | トナー |
JP2017215376A (ja) * | 2016-05-30 | 2017-12-07 | 京セラドキュメントソリューションズ株式会社 | 静電潜像現像用トナー |
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JP2003330225A (ja) * | 2002-05-17 | 2003-11-19 | Canon Inc | 非磁性トナーの製造方法 |
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JP2010139696A (ja) * | 2008-12-11 | 2010-06-24 | Canon Inc | トナー及びトナーの製造方法 |
JP2010145555A (ja) * | 2008-12-16 | 2010-07-01 | Canon Inc | トナーおよびトナーの製造方法 |
JP2013033233A (ja) * | 2011-06-28 | 2013-02-14 | Konica Minolta Business Technologies Inc | 静電荷像現像用トナー及び静電荷像現像用トナーの製造方法 |
JP2014013384A (ja) * | 2012-06-07 | 2014-01-23 | Kao Corp | 電子写真用トナー |
JP2015152818A (ja) * | 2014-02-17 | 2015-08-24 | キヤノン株式会社 | トナーの製造方法 |
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JP2017215376A (ja) * | 2016-05-30 | 2017-12-07 | 京セラドキュメントソリューションズ株式会社 | 静電潜像現像用トナー |
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