# US 5,330,871 A · Toner for developing electrostatic image > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,330,871 A - Document ID: US5330871A - Status: Granted - Kind: A - Application number: 07/797,915 - Filed: 1991-11-26 - Granted: 1994-07-19 - Earliest claimed: 1990-11-29 - Assignees: Canon Kabushiki Kaisha - Inventors: Hirohide Tanikawa; Masaki Uchiyama; Yoshinobu Joh; Yasutaka Akashi; Masaaki Taya; Makoto Unno - Web page: https://patentgrep.com/patent/US5330871A ## CPC - G03G 9/0821: {characterised by physical parameters (magnetic parameters G03G9/083)} - G03G 9/08797: {characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract A toner for developing an electrostatic image is constituted by a binder resin and a colorant. The binder resin is characterized by containing at least 20 wt. % of an extraction residue after 6 hours of extraction and below 20 wt. % of an extraction residue after 72 hours of extraction respectively by Soxhlet extraction with tetrahydrofuran. The toner shows a dynamic modulus and a loss modulus, respectively at 200.degree. C. and 0.1 Hz, which are substantially unchanging with time. The properties provide the toner with a harmonization of anti-offset characteristic and fixability as well as stable viscoelasticity under heating. ## Claims ### Claim 1 A toner for developing an electrostatic image, comprising: a binder resin, a metal-containing compound reactive with said binder resin and a colorant, wherein the binder resin contains (a) a first component of a low molecular weight in amounts of less than 80 wt. % detectable as an extract in 6 hours of extraction, and (b) a second component in amounts of at least 20 wt. % detectable as an extraction residue after 6 hours of extraction , said second component including (c) a third component of a tetrahydrofuran-non-extractable matter in amounts of below 20 wt. % detectable as an extraction residue after 72 hours of extraction; each said extraction being a Soxhlet extraction with tetrahydrofuran, wherein the toner shows a dynamic modulus and a loss modulus, respectively at 200.degree. C. and 0.1 Hz, which are substantially unchanging with time. ### Claim 2 (depends on 1) The toner according to claim 1, wherein the extraction residue after 6 hours is at least 2 times the extraction residue after 72 hours. ### Claim 3 (depends on 1) The toner according to claim 1, wherein the toner shows a dynamic modulus of 1.times.10.sup.3 -1.times.10.sup.5 dyn/cm.sup.2 and a loss modulus of 1.times.10.sup.2 -5.times.10.sup.4 dyn/cm.sup.2 as respectively measured at 200.degree. C. and 0.1 Hz, and the dynamic modulus is larger than the loss modulus. ### Claim 4 (depends on 1) The toner according to claim 1, wherein the extraction residue after 6 hours is 20-80 wt. % of the binder resin. ### Claim 5 (depends on 1) The toner according to claim 1, wherein the extraction residue after 6 hours is 25-70 wt. % of the binder resin. ### Claim 6 (depends on 1) The toner according to claim 1, wherein the extraction residue after 72 hours is below 15 wt. % of the binder resin. ### Claim 7 (depends on 1) The toner according to claim 1, wherein the extraction residue after 6 hours is 2-30 times the extraction residue after 72 hours. ### Claim 8 (depends on 1) The toner according to claim 1, wherein the moduli measured after holding the toner for 60 min. at 200.degree. C. are below two times the moduli before the holding. ### Claim 9 (depends on 1) The toner according to claim 1, wherein the moduli measured after holding the toner for 60 min. at 200.degree. C. are within the range of from 0.5 to below 2 times the moduli before the holding. ### Claim 10 (depends on 1) The toner according to claim 1, wherein the moduli measured after holding the toner for 60 min. at 200.degree. C. are within the range of 0.8-1.8 times the moduli before the holding. ### Claim 11 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a vinyl polymer, a vinyl copolymer, or a mixture thereof. ### Claim 12 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a crosslinked vinyl polymer, a crosslinked vinyl copolymer, or a mixture thereof. ### Claim 13 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a styrene polymer, a styrene copolymer, or a mixture thereof. ### Claim 14 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a crosslinked styrene polymer, a crosslinked styrene copolymer, or a mixture thereof. ### Claim 15 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a vinyl polymer, a vinyl copolymer or a mixture thereof having a JIS acid value of at most 100 mgKOH/g. ### Claim 16 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a vinyl polymer, a vinyl copolymer or a mixture thereof having a JIS acid value of 2-70 mgKOH/g. ### Claim 17 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a vinyl polymer, a vinyl copolymer or a mixture thereof having a JIS acid value of 5-60 mgKOH/g. ### Claim 18 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a polyester resin. ### Claim 19 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a polyester resin having a JIS acid value of at most 100 mgKOH/g. ### Claim 20 (depends on 1) The toner according to claim 1, wherein said binder resin comprises a polyester resin having a JIS acid value of at most 50 mgKOH/g. ### Claim 21 (depends on 1) The toner according to claim 1, wherein said binder resin contains an ultra-high molecular weight component formed by melt-kneading a resin material containing a THF-insoluble and highly crosslinked high molecular weight having a carboxyl group together with said metal-containing compound linkable with the carboxyl group to sever the crosslinked high molecular weight component and cause re-crosslinking of the severed crosslinked high-molecular weight component with the metal-containing compound. ### Claim 22 (depends on 1) The toner according to claim 1, wherein said metal-containing compound is an azo metal complex represented by the following formula: ##STR11## wherein M denotes a coordination center metal, inclusive of metal elements having a coordination number of 6, such as Sc, Ti, V, Cr, Co, Ni and Fe; Ar denotes an aryl group, such as phenyl or naphthyl, capable of having a substituent, examples of which may include: nitro, halogen, carboxyl, anilide, and alkyl and alkoxy having 1-18 carbon atoms; X, X', Y and Y' independently denote --O--, --CO--, --NH--, or --NR-- (wherein R denotes an alkyl having 1-4 carbon atoms; and A.sup..sym. denotes hydrogen, sodium, potassium, ammonium or aliphatic ammonium. ### Claim 23 (depends on 1) The toner according to claim 1, wherein said metal-containing an organic acid metal complex represented by the following formula: ##STR12## wherein M denotes a coordination center metal, inclusive of metal elements having a coordination number of 6, such as Cr, Co, Ni and Fe; A denotes ##STR13## capable of having a substituent, ##STR14## (X denotes hydrogen, halogen, or nitro), ##STR15## (R denotes hydrogen, C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.18 alkenyl); Y.sup..sym. denotes a counter ion, such as hydrogen, sodium, potassium, ammonium, or aliphatic ammonium; and Z denotes --O-- or --CO.O--. ### Claim 24 (depends on 1) The toner according to claim 1, wherein the third component is contained in an amount of 1 to 14.2 wt. % based on the binder resin.