WO2024085908A1 - Additif pour une particule de toner contenant des particules de silice traitées en surface avec un agent de couplage au silane et toner - Google Patents
Additif pour une particule de toner contenant des particules de silice traitées en surface avec un agent de couplage au silane et toner Download PDFInfo
- Publication number
- WO2024085908A1 WO2024085908A1 PCT/US2023/011372 US2023011372W WO2024085908A1 WO 2024085908 A1 WO2024085908 A1 WO 2024085908A1 US 2023011372 W US2023011372 W US 2023011372W WO 2024085908 A1 WO2024085908 A1 WO 2024085908A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mass
- toner particle
- less
- additive
- silica particles
- Prior art date
Links
- 239000002245 particle Substances 0.000 title claims abstract description 86
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 32
- 239000000654 additive Substances 0.000 title claims abstract description 30
- 230000000996 additive effect Effects 0.000 title claims abstract description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 239000011593 sulfur Substances 0.000 claims abstract description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
- 229920001225 polyester resin Polymers 0.000 claims description 25
- 239000004645 polyester resin Substances 0.000 claims description 25
- 239000007771 core particle Substances 0.000 claims description 17
- 239000003086 colorant Substances 0.000 claims description 15
- 238000004381 surface treatment Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- -1 polyethylene terephthalate Polymers 0.000 description 29
- 239000001993 wax Substances 0.000 description 16
- 229920000139 polyethylene terephthalate Polymers 0.000 description 12
- 239000005020 polyethylene terephthalate Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 150000003628 tricarboxylic acids Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000001060 yellow colorant Substances 0.000 description 3
- 229910000859 α-Fe Inorganic materials 0.000 description 3
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- GGQRKYMKYMRZTF-UHFFFAOYSA-N 2,2,3,3-tetrakis(prop-1-enyl)butanedioic acid Chemical compound CC=CC(C=CC)(C(O)=O)C(C=CC)(C=CC)C(O)=O GGQRKYMKYMRZTF-UHFFFAOYSA-N 0.000 description 1
- XZFVXANAQPHQBR-UHFFFAOYSA-N 2-(16-methylheptadec-16-enyl)butanedioic acid Chemical compound CC(=C)CCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O XZFVXANAQPHQBR-UHFFFAOYSA-N 0.000 description 1
- NEYNUNUKSPDPJM-UHFFFAOYSA-N 2-(16-methylheptadecyl)butanedioic acid Chemical compound CC(C)CCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O NEYNUNUKSPDPJM-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- HLOQHECIPXZHSX-MDZDMXLPSA-N 2-[(e)-dec-1-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\C(C(O)=O)CC(O)=O HLOQHECIPXZHSX-MDZDMXLPSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- DMNJWIGKABXQGQ-AATRIKPKSA-N 2-[(e)-hex-1-enyl]butanedioic acid Chemical compound CCCC\C=C\C(C(O)=O)CC(O)=O DMNJWIGKABXQGQ-AATRIKPKSA-N 0.000 description 1
- XACKAZKMZQZZDT-MDZDMXLPSA-N 2-[(e)-octadec-9-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCC(C(O)=O)CC(O)=O XACKAZKMZQZZDT-MDZDMXLPSA-N 0.000 description 1
- PFBBCIYIKJWDIN-BUHFOSPRSA-N 2-[(e)-tetradec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O PFBBCIYIKJWDIN-BUHFOSPRSA-N 0.000 description 1
- HYCNRDZKNBPHTC-UHFFFAOYSA-N 2-[2-[carboxy(hydroxy)methyl]phenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1C(O)C(O)=O HYCNRDZKNBPHTC-UHFFFAOYSA-N 0.000 description 1
- YSUHBROHWRSYSF-UHFFFAOYSA-N 2-[3-[carboxy(hydroxy)methyl]phenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=CC(C(O)C(O)=O)=C1 YSUHBROHWRSYSF-UHFFFAOYSA-N 0.000 description 1
- FKLAJCGHOJXZRK-UHFFFAOYSA-N 2-[4-[carboxy(hydroxy)methyl]phenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(C(O)C(O)=O)C=C1 FKLAJCGHOJXZRK-UHFFFAOYSA-N 0.000 description 1
- WSFYPFLCEFLXOZ-UHFFFAOYSA-N 2-decylbutanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)CC(O)=O WSFYPFLCEFLXOZ-UHFFFAOYSA-N 0.000 description 1
- YLAXZGYLWOGCBF-UHFFFAOYSA-N 2-dodecylbutanedioic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)CC(O)=O YLAXZGYLWOGCBF-UHFFFAOYSA-N 0.000 description 1
- GCVQVCAAUXFNGJ-UHFFFAOYSA-N 2-hexadecylbutanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O GCVQVCAAUXFNGJ-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- ZPJDFKVKOFGAFV-UHFFFAOYSA-N 2-octadecylbutanedioic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O ZPJDFKVKOFGAFV-UHFFFAOYSA-N 0.000 description 1
- FPOGSOBFOIGXPR-UHFFFAOYSA-N 2-octylbutanedioic acid Chemical compound CCCCCCCCC(C(O)=O)CC(O)=O FPOGSOBFOIGXPR-UHFFFAOYSA-N 0.000 description 1
- MWTDCUHMQIAYDT-UHFFFAOYSA-N 2-tetradecylbutanedioic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)CC(O)=O MWTDCUHMQIAYDT-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- BKFXSOCDAQACQM-UHFFFAOYSA-N 3-chlorophthalic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(O)=O BKFXSOCDAQACQM-UHFFFAOYSA-N 0.000 description 1
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 1
- DMEDOWYXHVUPMO-UHFFFAOYSA-N 4-(carboxymethyl)benzoic acid Chemical compound OC(=O)CC1=CC=C(C(O)=O)C=C1 DMEDOWYXHVUPMO-UHFFFAOYSA-N 0.000 description 1
- PBWGCNFJKNQDGV-UHFFFAOYSA-N 6-phenylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(N)=C1C1=CC=CC=C1 PBWGCNFJKNQDGV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- AAHZZGHPCKJNNZ-UHFFFAOYSA-N Hexadecenylsuccinicacid Chemical compound CCCCCCCCCCCCCCC=CC(C(O)=O)CC(O)=O AAHZZGHPCKJNNZ-UHFFFAOYSA-N 0.000 description 1
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N Octacosancarbonsaeure Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 1
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940090958 behenyl behenate Drugs 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 238000001595 flow curve Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- LGZHPCIDRRUTMI-UHFFFAOYSA-N pyrene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C=CC3=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C4=CC=C1C2=C43 LGZHPCIDRRUTMI-UHFFFAOYSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09708—Inorganic compounds
- G03G9/09716—Inorganic compounds treated with organic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09708—Inorganic compounds
- G03G9/09725—Silicon-oxides; Silicates
Definitions
- electrophotography a surface of a photoreceptor is uniformly charged, an electrostatically charged image is formed on the surface of the photoreceptor, an electrostatic latent image is developed with a developer including toner particles, and thereby the electrostatic latent image is visualized as a toner image.
- the toner image is transferred and fixed onto the surface of a recording medium, and thereby an image is formed.
- the additive for a toner particle contains silica particles surface- treated with a silane coupling agent, the agent containing at least one element selected from a group comprising fluorine and sulfur.
- the surface treatment of the silica particles is a hydrophobic treatment to make the surface of the silica particles hydrophobic. That is, the silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur is to make the surface of the silica particle hydrophobic.
- the surface treatment of the silica particles is a hydrophobic treatment to make the surface of the silica particles hydrophobic, and may be a treatment to impart a charge (for example, a negative charge) to the silica particles. That is, the silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur is to make the surface of the silica particle hydrophobic and to impart a charge (for example, a negative charge).
- the surface treatment of silica particles as described above is, in some examples, may be without using a silazane compound (for example, hexamethyldisilazane).
- a silazane compound for example, hexamethyldisilazane
- the additive for a toner particle that can be used without the regulation can be provided.
- Examples of a silane coupling agent containing fluorine include a silane coupling agent containing a perfluoroether group.
- the silane coupling agent containing a perfluoroether group may be, for example, a silane coupling agent represented by the following formula (1):
- the alkyl groups represented by R 1 , R 2 and R 3 may be linear or branched.
- the number of carbon atoms of the alkyl groups represented by R 1 , R 2 and R 3 may be 1 or more and 3 or less, m may be an integer of 4 or less, n may be an integer of 5 or less, 4 or less, 3 or less, or 2 or less.
- Examples of a silane coupling agent containing sulfur include a silane coupling agent containing a mercapto group.
- the alkyl groups represented by R 4 and R 5 may be linear or branched.
- the number of carbon atoms of the alkyl groups represented by R 4 and R 5 may be 1 or more and 3 or less.
- the alkylene group represented by R 6 may be linear or branched.
- the number of carbon atoms of the alkylene group represented by R 6 may be 1 or more and 4 or less, p may be 2 or 3.
- q may be 0 or 1.
- the average particle diameter of the silica particles may be 250 nm or less, 200 nm or less, 150 nm or less, 100 nm or less, 70 nm or less, or 50 nm or less, and may be 5 nm or larger, 10 nm or larger, or 20 nm or larger.
- the average particle diameter of the silica particles is measured by the method described below.
- a method for producing an additive for a toner particle described above may utilize surface-treating silica particles with a silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur.
- the silica particles may be a commercial product according to a desired average particle diameter or the like.
- alcohol for example, methanol
- the silica particles, and a basic aqueous solution for example, ammonia aqueous solution
- a silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur may be gradually added. The mixing may continue after the addition to perform the surface treatment of the silica particles.
- the silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur are as described above.
- the amount of the silane coupling agent added may be 1 part by mass or more or 2 parts by mass or more, and may be 5 parts by mass or less or 4 parts by mass or less, with respect to 100 parts by mass of the silica particles (i.e., the silica particles prior to the surface treatment).
- the surface of the silica particles may be hydrophobized with the silane coupling agent without using a silazane compound (for example, hexamethyldisilazane) used during the surface treatment of the silica particle. That is, the surface treatment of the silica particles is a surface treatment (hydrophobic treatment) in which a silazane compound (for example, hexamethyldisilazane) is not used.
- a silazane compound for example, hexamethyldisilazane
- the toner particle according to some examples contains a core particle and an additive externally added to the core particle.
- the additive is an additive for a toner particle as described above.
- the core particle contains a binder resin.
- the binder resin may contain a polyester resin.
- the binder resin may contain a first polyester resin having a softening point of 120 °C or higher (a polyester resin having a higher softening point) and a second polyester resin having a softening point of lower than 120 °C (a polyester resin having a lower softening point).
- the softening point in the present specification is defined as Tl/2 based on the flow curve of the resin measured using a flow tester (for example, "Flow Tester Model CFT-500" manufactured by Shimadzu Corporation).
- the softening point (Tl/2) is measured by the method described in Examples.
- the softening point of the first polyester resin may be 123 °C or higher, 125 °C or higher, or 130 °C or higher, and may be 160 °C or lower, 155 °C or lower, 150 °C or lower, or 145 °C or lower.
- the softening point may be 140 °C or lower, or 135 °C or lower.
- the softening point of the second polyester resin may be 118 °C or lower, 115 °C or lower, or 110 °C or lower, or may be 80 °C or higher, and may be 85 °C or higher or 90 °C or higher for low-temperature fixability and heat-resistant storability.
- the first polyester resin may be a polycondensate of a polyethylene terephthalate, a carboxylic acid, and a diol.
- the first polyester resin is obtained by subjecting a polyethylene terephthalate, a carboxylic acid, and a diol (hereinafter collectively referred to as a "first polycondensation component") to an esterification reaction. More specifically, for example, the first polyester resin can be obtained by causing an ester exchange reaction between ethylene glycol contained as a monomer unit in the polyethylene terephthalate and the diol, and causing polycondensation of the carboxylic acid.
- the number average molecular weight (Mn) of the polyethylene terephthalate may be 5,000 or higher, 10,000 or higher, or 15,000 or higher, and may be 60,000 or less, 55,000 or less, 50,000 or less, or 45,000 or less.
- the polyethylene terephthalate may be a recycled polyethylene terephthalate. In this case, environmentally-friendly toner particles may be provided.
- the amount (charge amount) of the polyethylene terephthalate may be 5% by mass or more, 10% by mass or more, or 20% by mass or more, and may be 85% by mass or less, 80% by mass or less, or 70% by mass or less, based on the total amount of the first polycondensation component.
- the carboxylic acid may be a polycarboxylic acid or an anhydride thereof.
- the polycarboxylic acid may contain a dicarboxylic acid or an anhydride thereof.
- Examples of the dicarboxylic acid include a dicarboxylic acid having a pendant group and a dicarboxylic acid having no pendant group.
- the dicarboxylic acid having a pendant group has a chain (pendant group) which is branched from a main chain having two carboxyl groups.
- the pendant group may be a chain hydrocarbon group, and may be an alkyl group or an alkenyl group.
- the carbon number of the pendant group may be 3 or more, 4 or more, 6 or more, 8 or more, 10 or more, or 12 or more, and may be 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, or 12 or less.
- Examples of the dicarboxylic acid having a pendant group include succinic acid having an alkyl group having 3 or more carbon atoms, succinic acid having an alkenyl group having 3 or more carbon atoms, alkylbissuccinic acid having an alkyl group having 3 or more carbon atoms, and alkenylbissuccinic acid having an alkenyl group having 3 or more carbon atoms.
- dicarboxylic acid examples include octylsuccinic acid, decylsuccinic acid, dodecylsuccinic acid, tetradecylsuccinic acid, hexadecylsuccinic acid, octadecylsuccinic acid, isooctadecylsuccinic acid, hexenylsuccinic acid, octenylsuccinic acid, decenylsuccinic acid, dodecenylsuccinic acid, tetrapropenyl succinic acid, tetradecenylsuccinic acid, hexadecenylsuccinic acid, isooctadecenylsuccinic acid, octadecenyl succinic acid, and nonenylsuccinic acid.
- dicarboxylic acid having no pendant group examples include adipic acid, phthalic acid, isophthalic acid, tetrachlorophthalic acid, chlorophthalic acid, nitrophthalic acid, p-carboxyphenylacetic acid, p-phenylene-2-acetic acid, m- phenylenediglycolic acid, p-phenylenediglycolic acid, o-phenylenediglycolic acid, diphenylacetic acid, diphenyl-p,p’-dicarboxylic acid, naphthal ene-l,4-dicarboxylic acid, naphthalene-l,5-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, anthracenedicarboxylic acid, and cyclohexanedicarboxylic acid.
- the carboxylic acid may contain a tricarboxylic acid or an anhydride thereof.
- tricarboxylic acid examples include trimellitic acid, naphthalenetricarboxylic acid, and pyrenetricarboxylic acid.
- the carboxylic acid may contain at least one selected from a group comprising a dicarboxylic acid or an anhydride thereof, and a tricarboxylic acid or an anhydride thereof, and contains at least one selected from a group comprising a dicarboxylic acid or an anhydride thereof having a pendant group, and a tricarboxylic acid or an anhydride thereof to obtain toner particles that exhibit no peak of the MDSC described above.
- the amount (charge amount) of the carboxylic acid may be 5% by mass or more, 10% by mass or more, or 15% by mass or more, and may be 65% by mass or less, 60% by mass or less, or 55% by mass or less, based on the total amount of the first polycondensation component.
- diol examples include aliphatic diols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butanediol, hexanediol, neopentyl glycol, and glycerin; alicyclic diols such as cyclohexanediol, cyclohexanedimethanol, and hydrogenated bisphenol A; and aromatic diols such as ethylene oxide adducts of bisphenol A and propylene oxide adducts of bisphenol A. These polyhydric alcohols may be used alone or in combination of two or more.
- the diol may contain an aromatic diol, and may include an aromatic diol (does not contain any diol other than the aromatic diol) for offset resistance and heat-resistant storability.
- the content of the diol may be 10% by mass or more, 15% by mass or more, or 20% by mass or more, and may be 70% by mass or less, 65% by mass or less, or 60% by mass or less, based on the total amount of the first polycondensation component.
- the second polyester resin may be a polycondensate of a carboxylic acid and a diol.
- the second polyester resin is obtained by subjecting a carboxylic acid and a diol (hereinafter, collectively referred to as "second polycondensation component") to an esterification reaction.
- the second polycondensation component may further contain a polyethylene terephthalate. Details of the carboxylic acid, the diol, and the polyethylene terephthalate are the same as those described for the first polyester resin.
- the weight average molecular weight of the first polyester resin is larger than the weight average molecular weight of the second polyester resin.
- the weight average molecular weight of the first polyester resin may be 20,000 or more, 30,000 or more, or 40,000 or more, and may be 80,000 or less, 75,000 or less, or 70,000 or less.
- the weight average molecular weight of the second polyester resin may be 5,000 or more, 6,000 or more, or 7,000 or more, and may be 30,000 or less, 20,000 or less, or 15,000 or less.
- the weight average molecular weights of the first and second polyester resins are measured by the method described in Examples.
- the content of the first polyester resin may be 2% by mass or more, 10% by mass or more, or 20% by mass or more, and may be 50% by mass or less, 45% by mass or less, or 40% by mass or less, based on the total amount of the binder resin.
- the content of the second polyester resin may be 50% by mass or more, 55% by mass or more, or 60% by mass or more, and or less, 90% by mass or less, or 80% by mass or less, based on the total amount of the binder resin.
- the content of the binder resin in the toner particles may be 40% by mass or more, 45% by mass or more, or 50% by mass or more, and may be 90% by mass or less, 85% by mass or less, or 75% by mass or less, based on the total amount of the toner particles.
- the core particle may further contain a colorant.
- the colorant may contain at least one colorant selected from, for example, a black colorant, a cyan colorant, a magenta colorant, and a yellow colorant.
- a black colorant e.g., a black colorant
- a cyan colorant e.g., a magenta colorant
- a yellow colorant e.g., a black colorant, a cyan colorant, a magenta colorant, and a yellow colorant.
- the colorant one kind is used alone, or two or more kinds are used as a mixture, in consideration of hue, chroma, brightness, weather-resistance, dispersibility in toner, and the like.
- the black colorant may be carbon black or aniline black.
- the yellow colorant may be a condensed nitrogen compound, an isoindolinone compound, an anthraquine compound, an azo metal complex, or an allylimide compound. Specific examples of the yellow colorant include C.I. Pigment Yellow 12, 13, 14, 17, 62, 74, 83, 93, 94, 95, 109, 110, 111, 128, 129, 147, 168, and 180.
- the magenta colorant may be a condensed nitrogen compound, anthraquine, a quinacridone compound, a basic dye lake compound, a naphthol compound, a benzimidazole compound, a thioindigo compound, or a perylene compound.
- Specific examples of the magenta colorant include C.I. Pigment Red 2, 3, 5, 6, 7, 23, 48:2, 48:3, 48:4, 57: 1, 81 : 1, 122, 144, 146, 166, 169, 177, 184, 185, 202, 206, 220, 221, and 254.
- the cyan colorant may be a copper phthalocyanine compound or a derivative thereof, an anthraquine compound, or the like. Specific examples of the cyan colorant include C.I. Pigment Blue 1, 7, 15, 15:1, 15:2, 15:3, 15:4, 60, 62, and 66.
- the content of the colorant may be 1% by mass or more, 2% by mass or more, or 3% by mass or more, and may be 10% by mass or less, 8% by mass or less, or 6% by mass or less, based on the total amount of the toner particle.
- the core particle may further contain a release agent.
- the release agent include a wax.
- the wax may be a natural wax or a synthetic wax.
- examples of the wax include a polyethylene wax, a polypropylene wax, a silicon wax, a paraffin wax, an ester wax, a carnauba wax, a beeswax, and a metallocene wax.
- the wax may be an ester wax.
- the ester wax may be, for example, an ester of a fatty acid having 15 to 30 carbon atoms and a monohydric alcohol having 10 to 30 carbon atoms, or may be an ester of a fatty acid having 15 to 30 carbon atoms and a polyhydric alcohol having 3 to 30 carbon atoms.
- Examples of the ester wax include behenyl behenate, stearyl stearate, stearic acid ester of pentaerythritol, and montanic acid glyceride.
- the melting point of the wax may be 60 °C or higher or 70 °C or higher, and may be 100 °C or lower or 90 °C or lower.
- the content of the wax may be 1% by mass or more, 2% by mass or more, or 3% by mass or more, and 15% by mass or less, 10% by mass or less, or 8% by mass or less, based on the total amount of the toner particle.
- the content (addition amount) of the additive may be 0.2 parts by mass or more, 0.5 parts by mass or more, or 1 part by mass or more, and may be 15 parts by mass or less, 10 parts by mass or less, or 7 parts by mass or less, with respect to 100 parts by mass of the core particle.
- the coverage of the additive for a toner particle (the surface-treated silica particle) on the surface of the toner particle may be 30% or more, 40% or more, or 50% or more, and may be 80% or less, 70% or less, or 60% or less, to obtain a suitable charge amount.
- the coverage is measured by the method described in Examples.
- the toner particle may further contain inorganic particles externally added to the core particle, in addition to the additive for a toner particle described above.
- examples of the inorganic particles include silica particles other than the surface-treated silica particles described above, alumina particles, zirconia particles, and titania particles.
- the average particle diameter of the toner particles may be 3 pm or larger, 4 pm or larger, or 5 pm or larger, and may be 12 pm or less, 11 pm or less, 10 pm or less, or 9 pm or less.
- the silica particles surface-treated with the silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur are externally added, the silica particles may function as a negative charge control agent, and thus the reversely charged toner may be reduced and a clear image with less fogging may be produced for a long time.
- the surface treatment of the silica particles may be a surface treatment in which a silazane compound (for example, hexamethyldisilazane) is not used, even when use of the silazane compound is legally regulated, toner particles that can be used without the regulation may be provided.
- a method for producing a toner particle described above includes surface-treating silica particles with a silane coupling agent containing at least one element selected from a group comprising fluorine and sulfur, and externally adding the surface-treated silica particles to core particle.
- the details of the surface-treating of the silica particles are as described above.
- the method for externally adding the surface-treated silica particles to the core particle may be a known method.
- the silica particles are externally added to the core particle by mixing the core particle and the silica particles with a powder mixer.
- the toner particles may be used as a one-component developer.
- the toner particles may be mixed with a magnetic carrier and used as a two-component developer for dot reproducibility and stability of images over a long period of time.
- the toner particles may be contained in a toner cartridge, for example. More specifically, the toner particles may be contained within a container in a toner cartridge. That is, some examples include a toner cartridge containing a container accommodating the above-described toner particles.
- the additive for a toner particle is described in more detail with reference to examples, but the additive for a toner particle is not limited to the examples.
- a 3 -liter glass reaction vessel equipped with a stirrer, a dropping funnel, and a thermometer is charged with 1500 g of methanol, 500 g of silica particles having particle diameters and specific gravities shown in Table 1, and 66.5 g of 28% ammonia aqueous solution, followed by mixing. Subsequently, at 25°C, a silane coupling agent whose type and addition amount are shown in Table 1 is added dropwise over 0.5 hours. After completion of the dropwise addition, stirring is continued for 12 hours to perform surface treatment of the silica particles.
- silica coupling agents are as follows.
- SCI silane coupling agent containing a perfluoroether group (in the above formula (1), R 1 , R 2 , and R 3 are -CH3 groups, m is 3, and n is 1)
- SC2 silane coupling agent containing a perfluoroether group (in the above formula (1), R 1 , R 2 , and R 3 are -CH3 groups, m is 3, and n is 2)
- the surface-treated silica particles are added in an amount shown in Table 2, and the mixture is mixed with a sample mill at 10000 rpm for 30 seconds to obtain toner particles.
- the addition amount of the surface-treated silica particles is adjusted so that the coverage of the surface-treated silica particles is equivalent except for Examples 10 and 15 in order to fairly compare the evaluation results of the charge amount described later.
- Coverage (%) [(particle diameter of toner particle: pm) x (specific gravity of toner particle: g/ml) x (mass ratio of toner particle to silica particle: %)] / [4 x (particle diameter of silica particle: pm) x (specific gravity of silica particle: g/ml)]
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- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
L'invention concerne un additif pour une particule de toner contenant des particules de silice traitées en surface avec un agent de couplage au silane contenant au moins un élément choisi dans un groupe comprenant le fluor et le soufre.
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JP2022-169333 | 2022-10-21 | ||
JP2022169333A JP2024086718A (ja) | 2022-10-21 | シランカップリング剤で表面処理されたシリカ粒子を含むトナー粒子用添加剤 |
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WO2024085908A1 true WO2024085908A1 (fr) | 2024-04-25 |
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PCT/US2023/011372 WO2024085908A1 (fr) | 2022-10-21 | 2023-01-23 | Additif pour une particule de toner contenant des particules de silice traitées en surface avec un agent de couplage au silane et toner |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0467439A1 (fr) * | 1990-07-19 | 1992-01-22 | Agfa-Gevaert N.V. | Composition révélatrice sèche électrostatographique |
US20040185367A1 (en) * | 2003-03-10 | 2004-09-23 | Fuji Xerox Co., Ltd. | Image forming method |
EP2040126A1 (fr) * | 2007-09-20 | 2009-03-25 | Fuji Xerox Co., Ltd. | Toner pour le développement d'images électrostatiques, son procédé de fabrication, développeur pour le développement d'images électrostatiques, cartouche de toner, cartouche de procédé, et appareil de formation d'images |
US20090214264A1 (en) * | 2008-02-21 | 2009-08-27 | Sharp Kabushiki Kaisha | Toner, method of manufacturing toner, developer, two-component developer, developing device, and image forming apparatus |
US20150248069A1 (en) * | 2014-02-28 | 2015-09-03 | Konica Minolta, Inc. | Image forming method |
US20150316889A1 (en) * | 2014-04-30 | 2015-11-05 | Konica Minolta, Inc. | Image forming process |
US20170315461A1 (en) * | 2016-04-28 | 2017-11-02 | Canon Kabushiki Kaisha | Toner and method of producing toner |
-
2023
- 2023-01-23 WO PCT/US2023/011372 patent/WO2024085908A1/fr unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0467439A1 (fr) * | 1990-07-19 | 1992-01-22 | Agfa-Gevaert N.V. | Composition révélatrice sèche électrostatographique |
US20040185367A1 (en) * | 2003-03-10 | 2004-09-23 | Fuji Xerox Co., Ltd. | Image forming method |
EP2040126A1 (fr) * | 2007-09-20 | 2009-03-25 | Fuji Xerox Co., Ltd. | Toner pour le développement d'images électrostatiques, son procédé de fabrication, développeur pour le développement d'images électrostatiques, cartouche de toner, cartouche de procédé, et appareil de formation d'images |
US20090214264A1 (en) * | 2008-02-21 | 2009-08-27 | Sharp Kabushiki Kaisha | Toner, method of manufacturing toner, developer, two-component developer, developing device, and image forming apparatus |
US20150248069A1 (en) * | 2014-02-28 | 2015-09-03 | Konica Minolta, Inc. | Image forming method |
US20150316889A1 (en) * | 2014-04-30 | 2015-11-05 | Konica Minolta, Inc. | Image forming process |
US20170315461A1 (en) * | 2016-04-28 | 2017-11-02 | Canon Kabushiki Kaisha | Toner and method of producing toner |
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