TW201120148A - Chemical toners comprising modified pigments - Google Patents
Chemical toners comprising modified pigments Download PDFInfo
- Publication number
- TW201120148A TW201120148A TW099119996A TW99119996A TW201120148A TW 201120148 A TW201120148 A TW 201120148A TW 099119996 A TW099119996 A TW 099119996A TW 99119996 A TW99119996 A TW 99119996A TW 201120148 A TW201120148 A TW 201120148A
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- Taiwan
- Prior art keywords
- group
- polymer
- pigment
- functional group
- modified pigment
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 353
- 239000000126 substance Substances 0.000 title claims abstract description 94
- 229920000642 polymer Polymers 0.000 claims abstract description 207
- 125000000524 functional group Chemical group 0.000 claims abstract description 135
- 239000000203 mixture Substances 0.000 claims abstract description 110
- 229920005989 resin Polymers 0.000 claims abstract description 59
- 239000011347 resin Substances 0.000 claims abstract description 59
- 125000000962 organic group Chemical group 0.000 claims abstract description 33
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 16
- -1 functional group anion Chemical class 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 12
- 125000000129 anionic group Chemical group 0.000 claims description 11
- 239000007859 condensation product Substances 0.000 claims description 11
- 230000000269 nucleophilic effect Effects 0.000 claims description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 125000005526 alkyl sulfate group Chemical group 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 4
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 150000004060 quinone imines Chemical class 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- DHIGSAXSUWQAEI-UHFFFAOYSA-N hydrazine azide Chemical compound NNN=[N+]=[N-] DHIGSAXSUWQAEI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002924 oxiranes Chemical class 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 239000000052 vinegar Substances 0.000 claims description 2
- 235000021419 vinegar Nutrition 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000013066 combination product Substances 0.000 abstract description 4
- 229940127555 combination product Drugs 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 description 81
- 239000002245 particle Substances 0.000 description 61
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 238000000034 method Methods 0.000 description 53
- 239000011521 glass Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000006229 carbon black Substances 0.000 description 28
- 235000019241 carbon black Nutrition 0.000 description 28
- 239000011324 bead Substances 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 238000002156 mixing Methods 0.000 description 20
- 239000013618 particulate matter Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 239000003973 paint Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229920001225 polyester resin Polymers 0.000 description 14
- 239000004645 polyester resin Substances 0.000 description 14
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 229960004050 aminobenzoic acid Drugs 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 11
- 238000000227 grinding Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical class [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000003010 ionic group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000011026 diafiltration Methods 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229950000244 sulfanilic acid Drugs 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000004931 aggregating effect Effects 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 238000010298 pulverizing process Methods 0.000 description 4
- 239000001054 red pigment Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
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- 239000012530 fluid Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000003701 mechanical milling Methods 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
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- 238000013112 stability test Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
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- 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
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
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- 241000251468 Actinopterygii Species 0.000 description 1
- 102100034111 Activin receptor type-1 Human genes 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RFTZTXYIRKTGQM-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)[N+]1=CC=CC=C1.[Br+] Chemical compound C(CCCCCCCCCCCCCCC)[N+]1=CC=CC=C1.[Br+] RFTZTXYIRKTGQM-UHFFFAOYSA-N 0.000 description 1
- IXAACKDTMBAVQV-UHFFFAOYSA-N C1=CC=CC2=CC3=CC=CC=C3C=C12.[S] Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C12.[S] IXAACKDTMBAVQV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 240000007108 Fuchsia magellanica Species 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 description 1
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Landscapes
- Physics & Mathematics (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26906909P | 2009-06-19 | 2009-06-19 |
Publications (1)
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| TW201120148A true TW201120148A (en) | 2011-06-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| TW099119996A TW201120148A (en) | 2009-06-19 | 2010-06-18 | Chemical toners comprising modified pigments |
Country Status (7)
| Country | Link |
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| EP (1) | EP2443521A4 (enExample) |
| JP (1) | JP6053518B2 (enExample) |
| KR (1) | KR20120027542A (enExample) |
| CN (1) | CN102804076A (enExample) |
| TW (1) | TW201120148A (enExample) |
| WO (1) | WO2010147647A2 (enExample) |
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| US8580469B2 (en) * | 2011-12-15 | 2013-11-12 | Xerox Corporation | Colored toners |
| CA2868399C (en) * | 2012-03-28 | 2017-07-04 | Cabot Corporation | Oxidized carbon blacks treated with polyetheramines and coating compositions comprising same |
| US8927648B2 (en) | 2012-05-04 | 2015-01-06 | Cabot Corporation | Surface modification of pigments and compositions comprising the same |
| CN113214682B (zh) * | 2021-04-12 | 2021-10-19 | 南京工业大学 | 一种高分散性群青颜料的制备方法及其所得颜料和应用 |
| CN118638436A (zh) * | 2024-08-12 | 2024-09-13 | 浙江材华科技有限公司 | 大分子染料化合物、其制备方法和日化用品 |
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| EP0787777A4 (en) * | 1995-06-14 | 2001-10-04 | Nippon Catalytic Chem Ind | GASKET POLYMER CONTAINING SOOT |
| US5830265A (en) * | 1996-10-31 | 1998-11-03 | Hewlett-Packard Company | Counterion substitution in macromolecular chromophore (MMC) for ink-jet printing including textile, large format and office format printers |
| US5976233A (en) * | 1996-11-13 | 1999-11-02 | Canon Kabushiki Kaisha | Water-based pigment ink, and ink-jet recording method and instruments using the same |
| US5955232A (en) * | 1997-07-22 | 1999-09-21 | Cabot Corporation | Toners containing positively chargeable modified pigments |
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| JP2001521972A (ja) * | 1997-10-31 | 2001-11-13 | キャボット コーポレイション | 結合した安定型フリーラジカルを持つ粒子、重合変性粒子、及びその製造方法 |
| WO1999051690A1 (en) * | 1998-04-03 | 1999-10-14 | Cabot Corporation | Modified pigments having improved dispersing properties |
| US6103380A (en) * | 1998-06-03 | 2000-08-15 | Cabot Corporation | Particle having an attached halide group and methods of making the same |
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| US6218067B1 (en) * | 1998-11-06 | 2001-04-17 | Cabot Corporation | Toners containing chargeable modified pigments |
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| EP1252237B1 (en) * | 2000-01-07 | 2006-08-09 | Cabot Corporation | Polymers and other groups attached to pigments and subsequent reactions |
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| US6833026B2 (en) * | 2002-05-10 | 2004-12-21 | Cabot Corporation | Modified pigments and process for preparing modified pigments |
| US6936097B2 (en) * | 2003-04-16 | 2005-08-30 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| US6942724B2 (en) * | 2003-04-16 | 2005-09-13 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| KR100657414B1 (ko) * | 2004-04-08 | 2006-12-13 | 주식회사 엘지화학 | 대전특성이 균일한 중합토너 |
| US8153706B2 (en) * | 2004-10-25 | 2012-04-10 | Hewlett-Packard Development Company, L.P. | Polymeric colorants having pigment and dye components and corresponding ink compositions |
| US7399566B2 (en) * | 2005-01-18 | 2008-07-15 | Milliken & Company | Color toner and developer compositions and processes for making and using such compositions |
| BRPI0607371A2 (pt) * | 2005-01-28 | 2009-09-01 | Cabot Corp | composição de toner e processo para preparar uma composição de toner |
| EP2160654A2 (en) * | 2007-06-08 | 2010-03-10 | Cabot Corporation | Carbon blacks, toners, and composites and methods of making same |
| JP4895999B2 (ja) * | 2007-12-28 | 2012-03-14 | 株式会社リコー | 静電荷像現像用トナー、並びに、現像剤、トナー入り容器、プロセスカートリッジ、画像形成方法、及び画像形成装置 |
-
2010
- 2010-06-16 KR KR1020127001413A patent/KR20120027542A/ko not_active Ceased
- 2010-06-16 JP JP2012516059A patent/JP6053518B2/ja active Active
- 2010-06-16 CN CN2010800368598A patent/CN102804076A/zh active Pending
- 2010-06-16 US US12/802,865 patent/US20100323289A1/en not_active Abandoned
- 2010-06-16 EP EP10789861A patent/EP2443521A4/en not_active Withdrawn
- 2010-06-16 WO PCT/US2010/001729 patent/WO2010147647A2/en not_active Ceased
- 2010-06-18 TW TW099119996A patent/TW201120148A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010147647A3 (en) | 2011-04-14 |
| CN102804076A (zh) | 2012-11-28 |
| JP2012530933A (ja) | 2012-12-06 |
| WO2010147647A2 (en) | 2010-12-23 |
| EP2443521A4 (en) | 2012-11-28 |
| EP2443521A2 (en) | 2012-04-25 |
| JP6053518B2 (ja) | 2016-12-27 |
| KR20120027542A (ko) | 2012-03-21 |
| US20100323289A1 (en) | 2010-12-23 |
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