EP0227874B1 - Toner for developing electrostatic latent images - Google Patents
Toner for developing electrostatic latent images Download PDFInfo
- Publication number
- EP0227874B1 EP0227874B1 EP19860100043 EP86100043A EP0227874B1 EP 0227874 B1 EP0227874 B1 EP 0227874B1 EP 19860100043 EP19860100043 EP 19860100043 EP 86100043 A EP86100043 A EP 86100043A EP 0227874 B1 EP0227874 B1 EP 0227874B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- toner
- acid
- resin
- parts
- zinc
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 4
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical group NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004135 Bone phosphate Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- DFYKHEXCUQCPEB-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C(C)=C DFYKHEXCUQCPEB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- -1 salicylic acid metal complex Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 2
- XBQCHPYJCIOWIX-UHFFFAOYSA-N 4-tert-butyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C(C)(C)C)=C(O)C(C(O)=O)=CC2=C1 XBQCHPYJCIOWIX-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PXOZAFXVEWKXED-UHFFFAOYSA-N chembl1590721 Chemical compound C1=CC(NC(=O)C)=CC=C1N=NC1=CC(C)=CC=C1O PXOZAFXVEWKXED-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- XGRZWVWRMKAQNU-UHFFFAOYSA-K 2-carboxyphenolate;chromium(3+) Chemical compound [Cr+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O XGRZWVWRMKAQNU-UHFFFAOYSA-K 0.000 description 1
- FOUQLSBYBRTDKN-UHFFFAOYSA-L 2-carboxyphenolate;cobalt(2+) Chemical compound [Co+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O FOUQLSBYBRTDKN-UHFFFAOYSA-L 0.000 description 1
- OZIKUNPJXSWSMD-UHFFFAOYSA-L 2-carboxyphenolate;manganese(2+) Chemical compound [Mn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O OZIKUNPJXSWSMD-UHFFFAOYSA-L 0.000 description 1
- DGOFDXKSKYTBGX-UHFFFAOYSA-L 2-carboxyphenolate;nickel(2+) Chemical compound [Ni+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O DGOFDXKSKYTBGX-UHFFFAOYSA-L 0.000 description 1
- 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 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 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 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UFCFPZYYZWIPDA-UHFFFAOYSA-N tert-butyl 2-hydroxybenzoate;cobalt Chemical compound [Co].CC(C)(C)OC(=O)C1=CC=CC=C1O UFCFPZYYZWIPDA-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 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
- G03G9/09783—Organo-metallic compounds
Definitions
- the present invention relates to a negatively chargeable toner of the dry type for developing electrostatic latent images in electrophotography, electrostatic recording, electrostatic printing as claimed in Claim 1.
- Electrostatic latent images can be developed into visible images with a toner which is caused to adhere to the image by electrostatic attraction.
- a toner which is caused to adhere to the image by electrostatic attraction.
- powder developers are widely used for developing electrostatic latent images.
- the powder developers are divided generally into two types: two-component developers comprising a toner having a mean particle size of 15 J.lm and a carrier of finely divided iron or ferrite mixed with the toner and 100 to 200 ⁇ m in particle size, the toner being composed of a natural resin or synthetic resin and a coloring agent, charge control agent, fluidizing agent, etc. dispersed in the resin; and one-component developers comprising a natural resin or synthetic resin, and a coloring agent, charge control agent, fluidizing agent and magnetic material which are dispersed in the resin.
- the toner is triboelectrically charged by the carrier and deposited on electrostatic images for development.
- the one-component developers heretofore known include toners which are chargeable by friction with a brush- or plate-like friction member serving the function of the carrier as a substitute therefor. Also made known in recent years is a toner which is chargeable by friction with a finely divided magnetic material which is maintained in a dispersed state. These developing toners are held positively or negatively charged in accordance with the polarity of the electrostatic latent image to be developed.
- these dyes and pigments as charge control agents are complex in structure and low in stability. They are susceptible to decomposition or degradation to lose charge control properties, owing for example to mechanical friction and impact, changes of temperature and humidity, electrical impact, irradiation with light, etc. Further one of their substantial defects is that these agents are colored substances and are therefore in conflict with the requirement that a colorless or substantially colorless charge control agent should be used for a toner having a particular color.
- the document DE-A 3 144 017 describes a toner containing a resin and, as a charge control agent, a Cr, Co or Fe complex of a substituted salicylic acid and of another aromatic hydroxycarboxylic acid having or not having a substituent.
- the metal complex is reported to have good compatibility with the resin component, to be substantially colorless, and to impart outstanding durability to the toner.
- the document DE-A 3 329 252 describes a toner containing an amorphous polyester having an acid number of 10 to 100 and being obtained by reacting an etherified diphenol with a benzene dicarboxylic acid or a mixture of benzene dicarboxylic acids, and a salicylic acid metal complex.
- the diphenol is either propoxylated or propoxylated and ethoxylated, wherein the content of propoxy groups is not less than 50 mole percent of the total content of the propoxy and ethoxy groups, and the benzene dicarboxylic acid or the mixture of benzene dicarboxylic acids contains up to 40 mole percent of a tribasic or higher-basic aromatic carboxylic acid.
- the metal complex is reported to react with and cross-link the polyester to improve the viscosity at melt and to prevent adhering of the toner to hot rollers during a fixing process.
- charge control agents such as metal-containing dyes and Nigrosin is described as being optional.
- the metal complex may be selected from zinc salicylate, chromium salicylate, manganese salicylate, nickel salicylate, cobalt salicylate, cobalt-t-butyl salicylate, chromium-3,5-di-t-butyl salicylate and nickel-3,5-di-t-butyl salicylate.
- the object of the present invention is to provide a toner containing a resin and, as a charge control agent capable of giving negative charges to the toner, a compound which remains thermally stable up to a temperature permitting thorough melting and kneading and which is colorless.
- the present invention provides a toner for developing electrostatic latent images, the toner containing a resin and, as a charge control agent, a metal complex of an aromatic hydroxycarboxylic acid having or not having a substituent.
- the toner is characterized in that the metal complex is a zinc complex, toners being excluded wherein the zinc complex is zinc salicylate and the resin is the specific amorphous polyester described in the document DE-A 3 329 252.
- Examples of useful aromatic hydroxycarboxylic acids which may have a substituent and which are capable of forming zinc complex compounds are alkyl(C4-C g )salicylic acids, 3,5-dialkyl(C 4 -Cs)salicylic acids, 2-hydroxy-3-naphthoic acid, alkyl(C 4 -Cs)-2-hydroxy-3-naphthoic acids, 5,6,7,8-tetrahalogen-2-hydroxy-3-naphthoic acids, etc.
- the zinc complex compound of the present invention can be prepared by dissolving a suitable hydroxycarboxylic acid in water with addition of a sufficient amount of alkali, adding to the solution a metallic zinc giving agent in the agent-to-acid mole ratio of 1:2, heating the mixture, adjusting the pH of the reaction mixture, filtering off the resulting precipitate, thoroughly wahing the precipitate with water and drying the precipitate.
- the product is represented by the formula wherein A and A ' are the residue of an aromatic hydroxycarboxylic acid which may have a substituent, and M is a counter ion.
- the counter ion can be changed by changing the condition for the aftertreatment of the reaction mixture. For example, when the reaction mixture is adjuted to a pH of up to 3, then filtered and thereafter washed until the pH becomes about 6 to about 7, the counter ion is hydrogen ion. If the pH is adjusted to neutrality to alkalinity with an alkali, alkali metal ion is obtained. Further if the mixture is treated with hydrochlorides of various amines, various ammonium salts are obtained.
- the complex compound of the formula (I) is incorporated into a toner generally in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, per 100 parts by weight of the component resin of the toner.
- the toner of the present invention is prepared by admixing the complex compound of the formula (I) with at least one of the resins heretofore known for use in toners, such as styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester resin, paraffin wax and the like.
- the resin to be used is determined in view of adhering properties, preservability, free-flowability, amenability to pulverization, etc.
- dyes and pigments are usable as coloring agents, especially suitable as coloring agents for toners for color copying are, for example, Benzidine Yellow, quinacridone, Copper Phthalocyanine Blue, Copper Phthalocyanine Green, etc.
- the toner is usually mixed with a carrier to provide a two-component developer, it is of course usable as a one-component developer.
- a 44.5 g (0.18 mole) quantity of 3,5-di-tert-butylsalicylic acid was completely dissolved in 400 g of 2% aqueous solution of caustic soda, and the solution was heated to about 70 ° C.
- Polyester resin (ATR-2010, product of Kao Soap Co., Ltd.) 100 parts Blue dye (Valifast Blue 2606, product of Orient Kagaku Kogyo Co., Ltd.) 2 parts Blue pigment (Copper Phthalocyanine) 4 parts Compound (1) 1 part
- the above ingredients were premixed uniformly by a ball mill to obtain a premix, which was kneaded in a molten state by heat rolls, then cooled, thereafter crushed by a vibrating mill and further pulverized by an air jet mill.
- the fine powder obtained was screened to obtain a blue toner 10 to 20 ⁇ m in particle size.
- the amount of initial blow-off charge on the developer was -28.3 ⁇ c/g.
- sharp blue toner images were obtained free from fog. Even after the toner was used for continuously making 50,000 copies, no reduction was observed in the quality of copies.
- Epoxy resin (Epikote 1004, product of Shell Chemical Co. Ltd.) 100 parts Carbon black 6 parts Compound (2) 2 parts
- the toner obtained Three parts of the toner obtained were admixed with 97 parts of a carrier of finely divided iron to prepare a developer.
- the amount of initial blow-off charge on the developer was -24.1 ⁇ c/g.
- sharp black toner images were obtained free from any fog.
- the toner exhibited no reduction in the quality of copies even after continuously making 50,000 copies.
- the toner obtained Three parts of the toner obtained were admixed with 97 parts of a carrier of finely divided iron to prepare a developer.
- the amount of initial blow-off charge on the developer was -25.2 l icfg.
- the developer When used for copying in the same manner as in Example 1, the developer produced toner images free from any fog and outstanding in reproducibility of thin lines.
- the toner exhibited no reduction in the quality of copies even after continuously making 50,000 copies.
- Styrene-n-butyl methacrylate copolymer resin 65/35) 100 parts Red dye (Valifast Pink 2310, product of Orient Kagaku Kogyo Co., Ltd.) 8 parts Compound (2) 2 parts
- a red toner was prepared from the above ingredients in the same manner as in Example 1. Three parts of the toner obtained were admixed with 97 parts of a carrier of finely divided iron to obtain a developer. The amount of initial blow-off charge on the developer was -22.9 I!c/g. When used for copying in the same manner as in Example 1, the developer produced sharp red toner images free from any fog. The toner exhibited no reduction in the quality of copies even after continuously making 50,000 copies.
- a yellow toner was prepared from the above ingredients in the same manner as in Example 1.
- the toner obtained Three parts of the toner obtained were admixed with 97 parts of a carrier of finely divided iron to obtain a developer.
- the amount of initial blow-off charge on the developer was -21.8 ⁇ c/g.
- the developer When used for copying in the same manner as in Example 1, the developer produced sharp yellow toner images free from any fog.
- the toner exhibited no reduction in the quality of copies even after continuously making 50,000 copies.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT86100043T ATE57025T1 (de) | 1986-01-03 | 1986-01-03 | Toner fuer die entwicklung elektrostatischer latenter bilder. |
| DE8686100043T DE3674562D1 (de) | 1986-01-03 | 1986-01-03 | Toner fuer die entwicklung elektrostatischer latenter bilder. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59191117A JPS6169073A (ja) | 1984-09-12 | 1984-09-12 | 静電荷像現像用トナ− |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0227874A1 EP0227874A1 (en) | 1987-07-08 |
| EP0227874B1 true EP0227874B1 (en) | 1990-09-26 |
Family
ID=16269146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19860100043 Expired EP0227874B1 (en) | 1984-09-12 | 1986-01-03 | Toner for developing electrostatic latent images |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0227874B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS6169073A (enrdf_load_stackoverflow) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762763A (en) * | 1985-12-19 | 1988-08-09 | Ricoh Co., Ltd. | Toner for developing electrostatic latent image |
| JP2572756B2 (ja) * | 1986-11-07 | 1997-01-16 | 三菱化学株式会社 | 静電荷像現像用トナ− |
| US4985328A (en) * | 1988-09-22 | 1991-01-15 | Hitachi Chemical Co., Ltd. | Dry toner, dry developer and process for forming electrophotographic images |
| US5153090A (en) * | 1990-06-28 | 1992-10-06 | Commtech International Management Corporation | Charge directors for use in electrophotographic compositions and processes |
| JPH03185457A (ja) * | 1989-12-15 | 1991-08-13 | Konica Corp | カラートナー |
| JP2609359B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電用電子写真用トナー |
| JP2609357B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電用電子写真用トナー |
| JP2609356B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電性電子写真用トナー |
| AU8897391A (en) * | 1990-12-12 | 1992-06-18 | Mitsubishi Kasei Corporation | Electrostatic image-developing toner |
| GB9306456D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Composition and use |
| SG73592A1 (en) | 1997-12-05 | 2000-06-20 | Canon Kk | Toner having negative triboelectric chargeability and developing method |
| DE69928159T2 (de) | 1998-04-10 | 2006-07-20 | Canon K.K. | Zweikomponenten-Entwickler und Bilderzeugungsverfahren |
| EP0961175B1 (en) | 1998-05-26 | 2006-01-25 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and image forming method |
| DE60300471T2 (de) | 2002-07-19 | 2006-02-23 | Ricoh Co., Ltd. | Toner welche Ladungskontrollmittel auf Basis von Zirkonium-Organometallischen Verbindungen enthalten und Bildgebungsverfahren |
| EP1978410A4 (en) | 2006-01-23 | 2011-09-28 | Hodogaya Chemical Co Ltd | PHOTO RECEPTOR FOR ELECTROPHOTOGRAPHY |
| WO2007111346A1 (ja) | 2006-03-29 | 2007-10-04 | Hodogaya Chemical Co., Ltd. | 混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| JP5343560B2 (ja) | 2006-04-13 | 2013-11-13 | 保土谷化学工業株式会社 | 酸化型混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| JP5759175B2 (ja) * | 2008-09-29 | 2015-08-05 | 日本碍子株式会社 | ガス吸着材料、その前駆体及びガス吸着材料の製造方法 |
| CN102741758A (zh) | 2010-02-26 | 2012-10-17 | 保土谷化学工业株式会社 | 电荷控制剂以及使用该电荷控制剂的调色剂 |
| JPWO2012035990A1 (ja) | 2010-09-13 | 2014-02-03 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| CN103238117A (zh) | 2010-09-14 | 2013-08-07 | 保土谷化学工业株式会社 | 电荷控制剂和使用其的调色剂 |
| US20130149641A1 (en) | 2010-09-15 | 2013-06-13 | Hodogaya Chemical Co., Ltd. | Charge controlling agent and toner using same |
| EP2669741A4 (en) | 2011-01-27 | 2016-05-11 | Hodogaya Chemical Co Ltd | LOAD CONTROLLER AND TONER THEREOF |
| JP2012177827A (ja) | 2011-02-28 | 2012-09-13 | Ricoh Co Ltd | トナー、このトナーを用いたフルカラー画像形成方法及びフルカラー画像形成装置 |
| WO2015046214A1 (ja) | 2013-09-24 | 2015-04-02 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| JP6720196B2 (ja) | 2015-09-17 | 2020-07-08 | 保土谷化学工業株式会社 | ピラゾロン誘導体または該誘導体の塩を用いた電荷制御剤およびトナー |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127726A (en) * | 1977-04-13 | 1978-11-08 | Canon Inc | Electrostatic image developing toner |
| JPS5779964A (en) * | 1980-11-06 | 1982-05-19 | Canon Inc | Developing method |
| JPS5841508B2 (ja) * | 1980-12-22 | 1983-09-12 | オリヱント化学工業株式会社 | 静電荷像現像用トナ− |
| JPS5929255A (ja) * | 1982-08-12 | 1984-02-16 | Canon Inc | 静電荷現像用トナ− |
| JPS5979256A (ja) * | 1982-10-29 | 1984-05-08 | Ricoh Co Ltd | 静電潜像現像用トナ− |
| JPS5988745A (ja) * | 1982-11-15 | 1984-05-22 | Hodogaya Chem Co Ltd | 電子写真用トナ− |
-
1984
- 1984-09-12 JP JP59191117A patent/JPS6169073A/ja active Granted
-
1986
- 1986-01-03 EP EP19860100043 patent/EP0227874B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0260183B2 (enrdf_load_stackoverflow) | 1990-12-14 |
| EP0227874A1 (en) | 1987-07-08 |
| JPS6169073A (ja) | 1986-04-09 |
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