# US 5,346,951 A · Releasing agents and resin compositions therewith > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,346,951 A - Document ID: US5346951A - Status: Granted - Kind: A - Application number: 08/091,255 - Filed: 1993-07-15 - Granted: 1994-09-13 - Earliest claimed: 1992-07-17 - Assignees: Sanyo Chemical Industries, Ltd. - Inventors: Ataru Suwada - Web page: https://patentgrep.com/patent/US5346951A ## CPC - C08G 77/442: containing vinyl polymer sequences - G03G 9/08773: {Polymers having silicon in the main chain, with or without sulfur, oxygen, nitrogen or carbon only} - G03G 9/08786: {Graft polymers} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract The present invention provides a releasing agent obtained by reacting of an organic polysiloxane having a hydroxyl group or an epoxy group with an ethylenically unsaturated dicarboxylic acid grafted polyolefin or a reaction product of said grafted polyolefin and an active hydrogen atom-containing compound selected from the group consisting of an alcohol, an amine and an aminoalcohol. This releasing agent can be used in a resin composition for use in electrophotographic toner. ## Claims ### Claim 1 A releasing agent obtained by reacting an orgainic polysiloxane comprising a hydroxyl group or an epoxy group with an ethylenically unsaturated dicarboxylic acid grafted polyolefin or with a reaction product of said grafted polyolefin and an active hydrogen atom-containing compound selected from the group consisting of an alcohol, an amine and an aminoalcohol. ### Claim 2 (depends on 1) The releasing agent according to claim 1, wherein said polyolefin is a low molecular weight polyolefin obtained by thermal degradation of a high molecular weight polyolefin. ### Claim 3 (depends on 1) The releasing agent according to claim 1, wherein said polyolefin is a polymer of ethylene. ### Claim 4 (depends on 1) The releasing agent according to claim 1, wherein said polyolefin has a number average molecular weight of 500 to 100,000. ### Claim 5 (depends on 1) The releasing agent according to claim 1, wherein said dicarboxylic acid is maleic anhydride. ### Claim 6 (depends on 1) The releasing agent according to claim 1, wherein said active hydrogen atom-containing compound is an aminoalcohol or a monohydric alcohol having 1 to 18 carbon atoms. ### Claim 7 (depends on 1) The releasing agent according to claim 1, wherein said polysiloxane has a epoxy equivalent of 200 to 10,000. ### Claim 8 (depends on 1) The releasing agent according to claim 1, wherein said reaction product of said grafted polyolefin and said alcohol is a half ester. ### Claim 9 (depends on 1) The releasing agent according to claim 1, which contains 0.1 to 5% by weight of a silicon atom, based on the total weight of said releasing agent. ### Claim 10 (depends on 1) The releasing agent according to claim 1, wherein said polysiloxane has a structure selected from one of the following formulae: ##STR2## wherein each of R.sub.1 to R.sub.7 is independently the same or different and is a monovalent group selected from the group consisting of methyl, propyl, dodecyl, phenyl, .beta.-phenylethyl or 3,3,3-trifluoropropyl; X is a an epoxy group or a hydroxyl group; and P and q are each independently 0 or an integer greater than 1, provided that the sum of P and q is an integer of from 10 to 1,000. ### Claim 11 (depends on 10) The releasing agent according to claim 10, wherein said epoxy group is selected from the group consisting of glycidyl, glycidyloxyalkyl and 3,4-oxocyclohexylalkyl. ### Claim 12 (depends on 10) The releasing agent according to claim 10, wherein said hydroxyl group is selected from the group consisting of hydroxypropyl, hydroxyisobutyl, hydroxyphenethyl, hydroxyethylpolyoxyethylenealkyl and hydroxypropylpolyoxypropylenealkyl. ### Claim 13 A resin composition comprising (i) 0.5 to 30% by weight, based on the total weight of said resin composition, of a releasing agent obtained by reacting an organic polysiloxane comprising a hydroxyl group or an epoxy group with an ethylenically unsaturated dicarboxylic acid grafted polyolefin or with a reaction product of said grafted polyolefin and an active hydrogen atom-containing compound selected from the group consisting of an alcohol, an amine and an aminoalcohol, and (ii) 70 to 99.5% by weight, based on the total weight of said resin composition, of a binder resin. ### Claim 14 (depends on 13) The resin composition according to claim 13, wherein said binder resin is a polymer of a styrenic monomer or a polyester. ### Claim 15 (depends on 13) The resin composition according to claim 13, wherein said binder resin is a polymer of a vinyl monomer selected from the group consisting of styrenic monomers, acrvlate esters, methacrylate esters, fumarate esters, acrylonitrile, methacrylic acid and methacrylamide, said polymer having a number average molecular weight of 2,000 to 15,000, a Z average molecular weight of at least 400,000 and a ratio of Z average molecular weight to number average molecular weight ranging from 50 to 600. ### Claim 16 (depends on 14) The resin composition according to claim 14, wherein said polymer of the styrenic monomer is a styrene-acrylate copolymer. ### Claim 17 (depends on 14) The resin composition according to claim 14, wherein said polyester comprises an alkylene oxide adduct of a phenolic resin and a polycarboxylic acid. ### Claim 18 (depends on 14) The resin composition according to claim 14, wherein said polyester comprises an alkylene oxide adduct of bisphenol A and a polycarboxylic acid. ### Claim 19 (depends on 15) The resin composition according to claim 15, wherein said polycarboxylic acid comprises trimetallitic acid. ### Claim 20 (depends on 13) A method of producing the resin composition according to claim 13, which comprises dissolving or dispersing said releasing agent into a solvent solution of said binder resin and removing said solvent. ### Claim 21 (depends on 20) The method according to claim 20, wherein said binder resin is a styrene-ethylenically unsaturated ester polymer. ### Claim 22 (depends on 1) A releasing agent according to claim 1, wherein said polyolefin is selected from the group consisting of polyethylene, ethylene-.alpha.-olefin copolymers, ethylene-vinyl acetate copolymers, ethylene-methacrylic acid copolymers, ethylene-acrylic acid copolymers, polypropylene, propylene-.alpha.-olefin copolymers, propylene-vinyl acetate copolymers, propylene-methacrylic acid copolymers, propylene-acrylic acid copolymers, polybutene, poly-4-methylpent-1-ene and mixtures thereof. ### Claim 23 (depends on 13) A resin composition according to claim 13, wherein said binder resin is selected from the group consisting of polyolefins, poly(vinylacetate), poly(vinylchloride), polyurethane, polyamides, poly(vinylbutyral), rosin, terpene resins, phenolic resins, petroleum resins, polymers of a vinyl monomer selected from the group consisting of styrenic monomers, acrylate esters, methacrylate esters, fumarate esters, acrylonitrile, methacrylic acid and methacrylamide, polyester resins and epoxy resins.