# US 5,700,617 A · Toner for developing electrostatic images and charge-controlling agent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,700,617 A - Document ID: US5700617A - Status: Granted - Kind: A - Application number: 08/727,219 - Filed: 1996-10-08 - Granted: 1997-12-23 - Earliest claimed: 1995-10-12 - Assignees: Canon Kabushiki Kaisha - Inventors: Tsuyoshi Takiguchi; Kenji Okado; Masaaki Taya; Ryoichi Fujita; Makoto Kanbayashi; Wakashi Iida; Tetsuya Ida - Web page: https://patentgrep.com/patent/US5700617A ## CPC - G03G 9/09733: {Organic compounds (G03G9/08782 takes precedence)} - G03G 9/09708: {Inorganic compounds} - G03G 9/09783: {Organo-metallic compounds} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract A toner for developing an electrostatic image is formed from toner particles containing a binder resin, a colorant, and a charge-controlling agent. The charge-controlling agent comprises an aromatic oxycarboxylic acid, a metal compound of the aromatic oxycarboxylic acid, and an inorganic compound formed from an inorganic anion and an inorganic cation. The aromatic oxycarboxylic acid, the metal compound of the aromatic carboxylic acid and the inorganic anion are contained in proportions of A (wt. %), B (wt. %) and C (ppm), respectively, satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.20/80, and 10.sup.2 .ltoreq.C. Because of the inclusion of an inorganic compound providing a sufficient amount of inorganic anion, the charge-controlling agent shows a stable charge-controlling characteristic, and the resultant toner exhibits a stable developing performance and transferability in continuous image formation in various environmental conditions. ## Claims ### Claim 1 A toner for developing an electrostatic image, comprising toner particles containing a binder resin, a colorant, and a charge-controlling agent; wherein the charge-controlling agent comprises an aromatic oxycarboxylic acid, a metal compound of the aromatic oxycarboxylic acid, and an inorganic compound formed from an inorganic anion and an inorganic cation, and the aromatic oxycarboxylic acid, the metal compound of the aromatic carboxylic acid and the inorganic anion are contained in proportions of A (wt. B (wt. %) and C (ppm), respectively, satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.20/80, and 10.sup.2 .ltoreq.C. ### Claim 2 (depends on 1) The toner according to claim 1, wherein A (wt. %) and B (wt. %) satisfy the following condition: 1/99.ltoreq.A/B.ltoreq.15/85. ### Claim 3 (depends on 1) The toner according to claim 1, wherein A (wt. %) and B (wt. %) satisfy the following condition: 1/99.ltoreq.A/B.ltoreq.10/90. ### Claim 4 (depends on 1) The toner according to claim 1, wherein the aromatic oxycarboxylic acid, the metal compound of the aromatic oxycarboxylic acid, the inorganic anion and the inorganic cation are contained in proportions of A (wt. %), B (wt. %), C (ppm) and D (ppm), respectively, satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.20/80, 10.sup.2 .ltoreq.C, and 3.times.10.sup.2 .ltoreq.C+D. ### Claim 5 (depends on 4) The toner according to claim 4, wherein C (ppm) is at least 2.times.10.sup.2 (ppm). ### Claim 6 (depends on 4) The toner according to claim 4, wherein A (wt. %), B (wt. %) and C (ppm) satisfy the following conditions: 1/99.ltoreq.A/B.ltoreq.15/85, and C.gtoreq.2.times.10.sup.2. ### Claim 7 (depends on 4) The toner according to claim 4, wherein A (wt. %), B (wt. %) and C (ppm) satisfy the following conditions: 1/99.ltoreq.A/B.ltoreq.10/90, and C.gtoreq.2.times.10.sup.2. ### Claim 8 (depends on 1) The toner according to claim 1, wherein the inorganic cation of the inorganic compound is an alkali metal ion. ### Claim 9 (depends on 1) The toner according to claim 1, wherein the inorganic anion of the inorganic compound is a sulfate ion or a halide ion. ### Claim 10 (depends on 1) The toner according to claim 1, wherein the aromatic oxycarboxylic acid is a substituted aromatic hydroxycarboxylic acid or a substituted aromatic alkoxycarboxylic acid. ### Claim 11 (depends on 10) The toner according to claim 10, wherein the aromatic oxycarboxylic acid has an alkyl group substituent. ### Claim 12 (depends on 1) The toner according to claim 1, wherein the aromatic oxycarboxylic acid is a compound selected from the group consisting of salicylic acid, alkylsalicylic acid, dialkylsalicylic acid, hydroxynaphthoic acid, and alkylhydroxynaphthoic acid. ### Claim 13 (depends on 1) The toner according to claim 1, wherein the aromatic oxycarboxylic acid is 3,5-di-tert-butylsalicylic acid or 5-tert-octylsalicylic acid. ### Claim 14 (depends on 1) The toner according to claim 1, wherein the metal compound of the aromatic oxycarboxylic acid comprises a metal having a valence of at least 2. ### Claim 15 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid aluminum compound, sodium ion and sulfate ion. ### Claim 16 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid chromium compound, sodium ion and sulfate ion. ### Claim 17 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid zinc compound, sodium ion and sulfate ion. ### Claim 18 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent comprises 5-tert-octylsalicylic acid, 5-tert-octylsalicylic acid aluminum compound, sodium ion and sulfate ion. ### Claim 19 (depends on 1) The toner according to claim 1, wherein the binder resin comprises a polymer selected from the group consisting of styrene copolymer, polyester resin and epoxy resin. ### Claim 20 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent is contained in an amount of 0.5-15 wt. parts per 100 wt. parts of the binder resin. ### Claim 21 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent is contained in an amount of 1-10 wt. parts per 100 wt. parts of the binder resin. ### Claim 22 (depends on 1) The toner according to claim 1, wherein the toner particles are negatively chargeable. ### Claim 23 (depends on 1) The toner according to claim 1, wherein the charge-controlling agent has a volume resistivity of at most 9.5.times.10.sup.8 ohm.cm. ### Claim 24 A charge-controlling agent, comprising an aromatic oxycarboxylic acid, a metal compound of the aromatic oxycarboxylic acid, and an inorganic compound formed from an inorganic anion and an inorganic cation, wherein the aromatic oxycarboxylic acid, the metal compound of the aromatic carboxylic acid and the inorganic anion are contained in proportions of A (wt. B (wt. %) and C (ppm), respectively, satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.20/80, and 10.sup.2 .ltoreq.C. 25. ### Claim 25 (depends on 24) The charge-controlling agent according to claim 24, wherein A (wt. %) and B (wt. %) satisfying the following condition: 1/99.ltoreq.A/B.ltoreq.15/85. ### Claim 26 (depends on 24) The charge-controlling agent according to claim 24, wherein A (wt. %) and B (wt. %) satisfying the following condition: 1/99.ltoreq.A/B.ltoreq.10/90. ### Claim 27 (depends on 24) The charge-controlling agent according to claim 24, wherein the aromatic oxycarboxylic acid, the metal compound of the aromatic oxycarboxylic acid, the inorganic anion and the inorganic cation are contained in proportions of A (wt. %), B (wt. %), C (ppm) and D (ppm), respectively, satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.20/80, 10.sup.2 .ltoreq.C, and 3.times.10.sup.2 .ltoreq.C+D. ### Claim 28 (depends on 27) The charge-controlling agent according to claim 27, wherein C (ppm) is at least 2.times.10.sup.2 (ppm). ### Claim 29 (depends on 27) The charge-controlling agent according to claim 27, wherein A (wt. %), B (wt. %) and C (ppm) satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.15/85, and C.gtoreq.2.times.10.sup.2. ### Claim 30 (depends on 27) The charge-controlling agent according to claim 27, wherein A (wt. %), B (wt. %) and C (ppm) satisfying the following conditions: 1/99.ltoreq.A/B.ltoreq.10/90, and C.gtoreq.2.times.10.sup.2. ### Claim 31 (depends on 24) The charge-controlling agent according to claim 24, wherein the inorganic cation of the inorganic compound is an alkali metal ion. ### Claim 32 (depends on 24) The charge-controlling agent according to claim 24, wherein the inorganic anion of the inorganic compound is a sulfate ion or a halide ion. ### Claim 33 (depends on 24) The charge-controlling agent according to claim 24, wherein the aromatic oxycarboxylic acid is a substituted aromatic hydroxycarboxylic acid or a substituted aromatic alkoxycarboxylic acid. ### Claim 34 (depends on 33) The charge-controlling agent according to claim 33, wherein the aromatic oxycarboxylic acid has an alkyl group substituent. ### Claim 35 (depends on 24) The charge-controlling agent according to claim 24, wherein the aromatic oxycarboxylic acid is a compound selected from the group consisting of salicylic acid, alkylsalicylic acid, dialkylsalicylic acid, hydroxynaphthoic acid, and alkylhydroxynaphthoic acid. ### Claim 36 (depends on 24) The charge-controlling agent according to claim 24, wherein the aromatic oxycarboxylic acid is 3,5-di-tert-butylsalicylic acid or 5-tert-octylsalicylic acid. ### Claim 37 (depends on 24) The charge-controlling agent according to claim 24, wherein the metal compound of the aromatic oxycarboxylic acid comprises a metal having a valence of at least 2. ### Claim 38 (depends on 24) The charge-controlling agent according to claim 24, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid aluminum compound, sodium ion and sulfate ion. ### Claim 39 (depends on 24) The charge-controlling agent according to claim 24, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid chromium compound, sodium ion and sulfate ion. ### Claim 40 (depends on 24) The charge-controlling agent according to claim 24, wherein the charge-controlling agent comprises di-tert-butylsalicylic acid, di-tert-butylsalicylic acid zinc compound, sodium ion and sulfate ion. ### Claim 41 (depends on 24) The charge-controlling agent according to claim 24, wherein the charge-controlling agent comprises 5-tert-octylsalicylic acid, 5-tert-octylsalicylic acid aluminum compound, sodium ion and sulfate ion. ### Claim 42 (depends on 24) The charge-controlling agent according to claim 24, having a negative charge-controllability. ### Claim 43 (depends on 24) The charge-controlling agent according to claim 24, having a volume resistivity of at most 9.5.times.10.sup.8 ohm.cm.