EP1598707A1 - Toner mit Pulverrundkorn und Verfahren - Google Patents
Toner mit Pulverrundkorn und Verfahren Download PDFInfo
- Publication number
- EP1598707A1 EP1598707A1 EP05010089A EP05010089A EP1598707A1 EP 1598707 A1 EP1598707 A1 EP 1598707A1 EP 05010089 A EP05010089 A EP 05010089A EP 05010089 A EP05010089 A EP 05010089A EP 1598707 A1 EP1598707 A1 EP 1598707A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- toner powder
- powder according
- pigment
- metallocene
- toner
- 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.)
- Withdrawn
Links
- 239000000843 powder Substances 0.000 title claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000002245 particle Substances 0.000 claims abstract description 22
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 239000000049 pigment Substances 0.000 claims description 133
- 239000001993 wax Substances 0.000 claims description 40
- 229920000098 polyolefin Polymers 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000112 cooling gas Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003570 air Substances 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000007751 thermal spraying Methods 0.000 claims description 2
- 239000007921 spray Substances 0.000 abstract description 2
- 239000002826 coolant Substances 0.000 abstract 1
- -1 cyclopentadienyl radicals Chemical class 0.000 description 14
- 239000000975 dye Substances 0.000 description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [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 5
- 239000012860 organic pigment Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000019241 carbon black Nutrition 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019239 indanthrene blue RS Nutrition 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 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 3
- 229940099800 pigment red 48 Drugs 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-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
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SOFRHZUTPGJWAM-UHFFFAOYSA-N 3-hydroxy-4-[(2-methoxy-5-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound COc1ccc(cc1N=Nc1c(O)c(cc2ccccc12)C(=O)Nc1cccc(c1)[N+]([O-])=O)[N+]([O-])=O SOFRHZUTPGJWAM-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- XCZXLLSPCNNZMM-UHFFFAOYSA-N antimony(3+) chromium(3+) oxygen(2-) titanium(4+) Chemical class [O--].[O--].[O--].[O--].[O--].[Ti+4].[Cr+3].[Sb+3] XCZXLLSPCNNZMM-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000004161 brilliant blue FCF Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical class [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002508 contact lithography Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-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
- 239000001054 red pigment Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical class [S-2].[Zn+2] DRDVZXDWVBGGMH-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
- G03G9/0827—Developers with toner particles characterised by their shape, e.g. degree of sphericity
-
- 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
- G03G9/0802—Preparation methods
-
- 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
- G03G9/0802—Preparation methods
- G03G9/0808—Preparation methods by dry mixing the toner components in solid or softened state
-
- 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
- G03G9/0802—Preparation methods
- G03G9/081—Preparation methods by mixing the toner components in a liquefied state; melt kneading; reactive mixing
-
- 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
- G03G9/0819—Developers with toner particles characterised by the dimensions of the particles
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08704—Polyalkenes
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08775—Natural macromolecular compounds or derivatives thereof
- G03G9/08782—Waxes
Definitions
- the present invention relates to a toner powder, a method for the same Production and its use.
- toner powdered print media
- Electrophotographic processes transferred to the documents to be printed and then - usually thermally - fixed.
- the stated toners are usually made of a resin component, a colorant, usually a pigment and functional additives, which the Support processing, built.
- CPT called chemically produced toner
- round particles are obtained which subsequently first from the liquid polymerization medium by filtration and drying be separated and then classified into the desired grain size.
- the present invention therefore relates to a toner powder which is characterized characterized in that the powder particles have a round shape.
- the particle diameter of the powder particles is preferably 1 to 50 ⁇ m, preferably 5 to 20 microns and more preferably 8 to 15 microns.
- the toner powder contains at least one metallocene wax.
- the toner powder contains at least one metallocene wax and at least a pigment.
- the toner powder contains at least one metallocene wax, at least one pigment and at least one additive.
- the additive is a charge control agent.
- the metallocene waxes are polyolefin waxes, preferably to homopolymers of ethylene or propylene or copolymers of Ethylene or propylene with each other or with one or more 1-olefins with 4 to 50, preferably with 4 to 20 C atoms.
- the metallocene waxes are polyolefin waxes having a dropping point between 90 and 160 ° C, preferably between 100 and 155 ° C, a melt viscosity at 140 ° C between 10 and 10,000 mPa.s, preferably between 50 and 5000 mPa.s and a Density at 20 ° C between 0.89 and 0.96 cm 3 / g, preferably between 0.91 and 0.94 cm 3 / g.
- the metallocene waxes are polar modified.
- the invention also relates to a process for the preparation of the invention Toner powder, which is characterized in that a metallocene wax melts and then using a thermal spray method above the Melting point of the metallocene wax first atomized to droplets and then in a cooling gas atmosphere to solidify to round particles
- the gas of the cooling gas atmosphere is air, Nitrogen or mixtures thereof.
- the thus obtained round particles are preferably introduced by a Classified fractionation process.
- the upper and lower grain fractions of the classified powder are preferred again melted and returned to the process.
- the invention also relates to the use of the toner powder according to the invention for the production of printed matter.
- the invention also relates to the use of the toner powder according to the invention in or for digital printing.
- the invention also relates to the use of the toner powder according to the invention in or for photocopiers and printing presses.
- the present invention thus relates to the use of a polyolefin which a dropping point between 40 and 160 ° C, a melt viscosity of 2 to 20,000 mPa.s, and having a needle penetration number of 1 to 50.
- the dropping point is according to DIN 51801, Edition 1980-12, the melt viscosity after DIN 53018-1 and -2, Issue 1976-03 and the needle penetration number after DIN 51579, issue 1965-05 determined.
- polyolefin waxes are homopolymers of ethylene or propylene or Copolymers of ethylene or propylene with each other or with one or several 1-olefins in question.
- 1-olefins are linear or branched olefins with 4-18 C-atoms, preferably 4-6 C-atoms used. Examples are 1-butene, 1-hexene, 1-octene or 1-octadecene, furthermore styrene.
- Preferred are Copolymers of ethylene with propene or 1-butene. The copolymers are too 70-99.9, preferably to 80-99 wt .-% of ethylene.
- Metallocene catalysts for the preparation of the polyolefin waxes are chiral or nonchiral transition metal compounds of the formula M 1 L x .
- the transition metal compound M 1 L x contains at least one metal central atom M 1 , to which at least one ⁇ ligand, for example a cyclopentadienyl ligand, is bound.
- substituents such as halogen, alkyl, alkoxy or aryl groups may be bonded to the central metal atom M 1 .
- M 1 is preferably an element of III., IV., V. or VI.
- Cyclopentadienyl ligand is understood as meaning unsubstituted cyclopentadienyl radicals and substituted cyclopentadienyl radicals, such as methylcyclopentadienyl, indenyl, 2-methylindenyl, 2-methyl-4-phenylindenyl, tetrahydroindenyl or octahydrofluorenyl radicals.
- the ⁇ ligands may be bridged or unbridged, with single and multiple bridging - including ring systems - are possible.
- the term metallocene also includes compounds having more than one metallocene fragment, so-called polynuclear metallocenes. These can have any substitution patterns and bridging variants.
- the individual metallocene fragments of such polynuclear metallocenes may be both the same and different. Examples of such polynuclear metallocenes are described, for example, in EP-A-0 632 063.
- polar modified metallocene waxes are also suitable.
- the polar Modification of these polyolefin waxes can be achieved by oxidation with oxygen or oxygen-containing gases below or above the melting point.
- the wax is in the molten state at temperatures between the melting point of the wax and 200 ° C by introducing Oxygen or oxygen-containing gases, preferably air, oxidized.
- Oxidation modified waxes have acid numbers between 0.1 and 100, preferably 1 and 30 mg KOH / g, melt viscosities, measured at 170 ° C, from 5 to 10000 mPa.s, preferably 20 to 5000 mPa.s and softening points of 80 to 160 ° C on.
- oxidates such as by their esterification with mono- or polyhydric aliphatic or aromatic Alcohols, e.g. Ethanol, propanols, butanols, ethanediol, butanediols, glycerol, Trimethylolpropane, pentaerythritol or benzyl alcohol can be produced.
- Ethanol propanols, butanols, ethanediol, butanediols, glycerol, Trimethylolpropane, pentaerythritol or benzyl alcohol
- further derivatization is such Ester, for example, by esterification with acid components such as acrylic acid or Methacrylic acid possible.
- polar modification is the implementation of the Polyolefin wax with ⁇ , ⁇ -unsaturated carboxylic acids or their derivatives, optionally in the presence of a radical initiator.
- ⁇ , ⁇ -unsaturated carboxylic acids may be mentioned acrylic acid, methacrylic acid, Crotonic acid and maleic acid.
- derivatives of ⁇ , ⁇ -unsaturated Carboxylic acids are their esters or amides or anhydrides, e.g. Acrylic acid alkyl esters, acrylic acid amides, maleic acid diesters or diesters, Maleic anhydride or amides of maleic acid, e.g. Maleimide or N-alkyl substituted Called maleinimides.
- maleic acid and its derivatives especially preferred is maleic anhydride.
- the ⁇ , ⁇ -unsaturated carboxylic acids or their Derivatives come in an amount, based on polyolefin wax, from 0.1-20% by weight. The preparation of such radically generated polar Reaction products are described for example in EP 0941257.
- melt viscosities measured at 170 ° C, of 5 to 10,000 mPa.s, preferably 10 to 5000 mPa.s, saponification numbers of 0.1 to 100 mg KOH / g, preferably 2 to 80 mg KOH / g and softening points of 80 to 160 ° C, preferably 100 to 155 ° C on.
- wax products by Free radical conversion of polyolefin waxes with styrene in an amount of 0.1 - 30 wt .-%, based on the polyolefin wax used were prepared.
- the powder according to the invention may contain at least one further wax.
- These are preferably polyolefins, with Ziegler catalysts were made to natural waxes such as candelilla waxes, or beeswax Carnauba Waxes, or around montan waxes and their derivatives, Fischer-Tropsch Synthesized waxes, whether or not in polar modified form Polysiloxane-modified alkyls.
- the powder of the invention may further contain resins which are natural Origin or synthetically produced.
- Resins as they are in According to the invention can be contained powder, are hydrocarbon resins Base of abietic acid or based on cumarone-indene.
- Synthetic resins are based on ethylene-vinyl acetate copolymer, styrene-acrylate, polyester or Constructed polysiloxanes.
- the usable resins of the invention have a softening point of 30 - 150 ° C.
- pigments in the context of the present invention Inclusion pigments as used for ceramic paints.
- Suitable pigment is also a finely divided organic or inorganic Pigment and / or an organic dye or a mixture of different organic and / or inorganic pigments and / or organic dyes.
- the pigments can be in the form of dry powder as well water-moist press cake are used.
- phthalocyanine quinacridone, Perylene, perinone, thioindigo, anthanthrone, anthraquinone, flavanthrone, Indanthrone, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, Is
- Suitable inorganic pigments are, for example, titanium dioxides, zinc sulfides, Iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, Cobalt oxides and bismuth vanadates.
- Organic dyes include acid dyes, direct dyes, Sulfur dyes and their leuco form, metal complex dyes or Reactive dyes into consideration, wherein in the case of reactive dyes with Nucleophiles reacted dyes can be used.
- those are suitable whose use a blue scale determined light fastness with a grade greater than 5, in particular greater than 6 is judged.
- those for the preparation of the preparations pigments used to be as finely divided as possible, with preference 95% and more preferably 99% of the pigment particles have a particle size ⁇ 500 nm.
- the mean particle size is ideally at a value ⁇ 150 nm.
- the morphology of the Pigment particles very much different, and accordingly, the Viscosity behavior of the pigment preparations as a function of the particle shape be very different. Preference is given to pure or subsequently purified Pigments with as few organic or inorganic impurities as possible used.
- organic pigments there are carbon black pigments, such as e.g. Gas or furnace carbon black; Monoazo and disazo pigments, especially the color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow 83, Pigment Yellow 87, Pigment Yellow 97, Pigment Yellow 111, Pigment Yellow 126, Pigment Yellow 127, Pigment Yellow 128, Pigment Yellow 155, Pigment Yellow 174, Pigment Yellow 176, Pigment Yellow 191, Pigment Red 38, Pigment Red 144, Pigment Red 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 or Pigment Brown 41; ⁇ -naphthol and naphthol AS pigments, in particular the Color Index pigments Pigment Red 2, Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 9,
- organic dyes are the color index dyes acid Yellow 17, Acid Yellow 23, Direct Yellow 86, Direct Yellow 98, Direct Yellow 132, Reactive Yellow 37, Acid Red 52, Acid Red 289, Reactive Red 23, Reactive Red 180, Acid Blue 9, Direct Blue 199 and those reacted with nucleophiles To name reactive dyes.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004024700 | 2004-05-19 | ||
| DE102004024700A DE102004024700A1 (de) | 2004-05-19 | 2004-05-19 | Pulverrundkorn |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1598707A1 true EP1598707A1 (de) | 2005-11-23 |
Family
ID=34936318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05010089A Withdrawn EP1598707A1 (de) | 2004-05-19 | 2005-05-10 | Toner mit Pulverrundkorn und Verfahren |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20050260513A1 (ja) |
| EP (1) | EP1598707A1 (ja) |
| JP (1) | JP2005331953A (ja) |
| DE (1) | DE102004024700A1 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4788361B2 (ja) * | 2006-01-31 | 2011-10-05 | 日本ゼオン株式会社 | 電子写真用トナー |
| US8097391B2 (en) | 2006-01-31 | 2012-01-17 | Zeon Corporation | Toner for developing electrostatic image |
| JP5033590B2 (ja) * | 2007-11-12 | 2012-09-26 | 株式会社リコー | トナーの製造方法並びにトナー |
| US20150104741A1 (en) * | 2013-10-10 | 2015-04-16 | Xerox Corporation | Toner additives for tunable gloss |
| EP3289027B1 (de) * | 2015-04-29 | 2020-01-15 | Clariant International Ltd | Kurzkettige polyethylen-homopolymere mit verbesserter mahlbarkeit |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212837A (en) * | 1977-05-04 | 1980-07-15 | Tokyo Shibaura Electric Co., Ltd. | Method and apparatus for forming spherical particles of thermoplastic material |
| US4535049A (en) * | 1982-08-04 | 1985-08-13 | Mita Industrial Co., Ltd. | Pressure-fixing toner for electrophotography and process for preparation thereof |
| EP0843222A1 (en) * | 1995-08-02 | 1998-05-20 | Hoechst Research & Technology Deutschland GmbH & Co. KG | Electrophotographic toner |
| US6197468B1 (en) * | 1998-08-26 | 2001-03-06 | Konica Corporation | Toner and image forming method |
| EP1176470A2 (en) * | 2000-07-28 | 2002-01-30 | Canon Kabushiki Kaisha | Dry toner, image forming method and process cartridge |
| EP1249735A2 (en) * | 2001-04-10 | 2002-10-16 | Canon Kabushiki Kaisha | Dry toner, toner production process, image forming method and process cartridge |
| EP1318433A2 (de) * | 2001-12-06 | 2003-06-11 | Clariant GmbH | Verwendung von polar modifizierten Polyolefinwachsen in elektrophotographischen Tonern |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL300538A (ja) * | 1962-11-24 | |||
| JP2612568B2 (ja) * | 1986-03-07 | 1997-05-21 | 東洋インキ製造株式会社 | 電子写真用トナー |
| US6462128B1 (en) * | 2000-07-14 | 2002-10-08 | Clariant International Ltd. | Process of making finely divided opaque particles |
| JP4385517B2 (ja) * | 2000-11-24 | 2009-12-16 | コニカミノルタビジネステクノロジーズ株式会社 | 静電荷像現像用トナー |
| US6495302B1 (en) * | 2001-06-11 | 2002-12-17 | Xerox Corporation | Toner coagulant processes |
-
2004
- 2004-05-19 DE DE102004024700A patent/DE102004024700A1/de not_active Withdrawn
-
2005
- 2005-05-10 EP EP05010089A patent/EP1598707A1/de not_active Withdrawn
- 2005-05-18 JP JP2005145098A patent/JP2005331953A/ja not_active Withdrawn
- 2005-05-19 US US11/132,820 patent/US20050260513A1/en not_active Abandoned
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212837A (en) * | 1977-05-04 | 1980-07-15 | Tokyo Shibaura Electric Co., Ltd. | Method and apparatus for forming spherical particles of thermoplastic material |
| US4535049A (en) * | 1982-08-04 | 1985-08-13 | Mita Industrial Co., Ltd. | Pressure-fixing toner for electrophotography and process for preparation thereof |
| EP0843222A1 (en) * | 1995-08-02 | 1998-05-20 | Hoechst Research & Technology Deutschland GmbH & Co. KG | Electrophotographic toner |
| US6197468B1 (en) * | 1998-08-26 | 2001-03-06 | Konica Corporation | Toner and image forming method |
| EP1176470A2 (en) * | 2000-07-28 | 2002-01-30 | Canon Kabushiki Kaisha | Dry toner, image forming method and process cartridge |
| EP1249735A2 (en) * | 2001-04-10 | 2002-10-16 | Canon Kabushiki Kaisha | Dry toner, toner production process, image forming method and process cartridge |
| EP1318433A2 (de) * | 2001-12-06 | 2003-06-11 | Clariant GmbH | Verwendung von polar modifizierten Polyolefinwachsen in elektrophotographischen Tonern |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005331953A (ja) | 2005-12-02 |
| DE102004024700A1 (de) | 2005-12-15 |
| US20050260513A1 (en) | 2005-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1204005B1 (de) | Verwendung von gecoateten Pigmentgranulaten in elektrophotographischen Tonern und Entwicklern, Pulverlacken und Ink-Jet-Tinten | |
| EP2020420B1 (de) | Hochkristalline Polypropylenwachse | |
| DE10204304A1 (de) | Pigmentgranulate | |
| EP1598707A1 (de) | Toner mit Pulverrundkorn und Verfahren | |
| JP2009544775A (ja) | 有色水性ポリマー分散物、及びそれの製造及び使用 | |
| DE69124042T2 (de) | Körniger Farbstoff und dessen Herstellungsverfahren | |
| KR100837180B1 (ko) | 안료 과립의 제조 방법 | |
| JP2002317054A (ja) | 着色樹脂組成物の製造方法およびその利用 | |
| EP1332183B1 (de) | Phthalsäureimide als synergisten zur verbesserung der eigenschaften wässriger pigmentpräparationen | |
| EP3289027B1 (de) | Kurzkettige polyethylen-homopolymere mit verbesserter mahlbarkeit | |
| EP2486099B1 (de) | Leicht dispergierbare pigmentzubereitung auf basis von c.i. pigment yellow 155 | |
| JPH10251533A (ja) | 易分散キナクリドン顔料およびその製造方法 | |
| EP1163294B1 (de) | Purpurfarbene pigmentzusammensetzung und deren verwendung | |
| JP3996388B2 (ja) | 微粒子状着色樹脂の製造方法、微粒子状着色樹脂および物品の着色方法 | |
| US7300512B2 (en) | Method of making pigment dispersion containing a carrier such as castor oil or vegetable wax | |
| DE68922292T2 (de) | Verfahren zur Herstellung von pulverförmigen Zusammensetzungen, die Farbstoffe und/oder Pigmente enthalten und die unter Verwendung dieser Zusammensetzungen erthaltenen Produkte. | |
| DE2619878A1 (de) | Pelletisierbares pigmentkonzentrat | |
| EP0101666B1 (de) | Mahlen von organischen Pigmenten | |
| JP3562185B2 (ja) | 顔料組成物およびそれを用いた被覆剤 | |
| JPH02175770A (ja) | 顔料樹脂組成物の製造方法 | |
| JP4713821B2 (ja) | 微粒子状光硬化性樹脂の製造方法、微粒子状光硬化性樹脂および物品の表面処理方法 | |
| DE102009034914A1 (de) | Pigmentkonzentrate | |
| EP1417265A2 (en) | Liquid colour compositions with acyglycerols as dispersants | |
| JP2985211B2 (ja) | 固形描画材の製造方法 | |
| DE1571883A1 (de) | Verfahren zur Herstellung von Russdispersionen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR |
|
| AX | Request for extension of the european patent |
Extension state: AL BA HR LV MK YU |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH |
|
| 17P | Request for examination filed |
Effective date: 20060523 |
|
| AKX | Designation fees paid |
Designated state(s): DE ES FR GB IT NL |
|
| 17Q | First examination report despatched |
Effective date: 20080318 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Effective date: 20080911 |