# US 5,348,830 A · Poliymide toner and developer compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,348,830 A - Document ID: US5348830A - Status: Granted - Kind: A - Application number: 08/144,455 - Filed: 1993-09-20 - Granted: 1994-09-20 - Earliest claimed: 1993-09-20 - Assignees: Xerox Corporation - Inventors: Guerino G. Sacripante - Web page: https://patentgrep.com/patent/US5348830A ## CPC - G03G 9/08759: {Polyethers} - G03G 9/08768: {Other polymers having nitrogen in the main chain, with or without oxygen or carbon only} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract A toner composition comprised of a pigment, and thermotropic liquid crystalline polyimide of the formula ##STR1## wherein m represents the number of monomer segments present; X is a symmetrical moiety independently selected from the group consisting of phenyl, naphthyl, cyclohexyl, or bicycloaliphatic; and R is independently selected from the group consisting of alkyl, oxyakylene and polyoxyalkylene. ## Claims ### Claim 1 A toner comprised of a pigment, and a thermotropic liquid crystalline polyimide of the formula ##STR11## wherein m represents the number of monomer segments present; X is a symmetrical moiety independently selected from the group consisting of phenyl, naphthyl, cyclohexyl, or bicycloaliphatic; and R is independently selected from the group consisting of alkyl, oxyalkylene and polyoxyalkylene. ### Claim 2 (depends on 1) A toner in accordance with claim 1 wherein R is alkyl with from 1 to about 25 carbon atoms. ### Claim 3 (depends on 1) A toner in accordance with claim 1 wherein R is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, stearyl, lauryl, or mixtures thereof. ### Claim 4 (depends on 1) A toner in accordance with claim 1 wherein X is selected from the group consisting of bicyclo[2.2.2]oct-7-ene, perylene, and mixtures thereof. ### Claim 5 (depends on 1) A toner in accordance with claim 1 wherein R is an oxyalkylene selected from the group consisting of diethylene oxide, dipropylene oxide, triethylene oxide, tripropylene oxide, tetraethylene oxide, tetrapropylene oxide, pentaethylene oxide, pentapropylene oxide, polypropylene oxide, and mixtures thereof. ### Claim 6 (depends on 1) A toner in accordance with claim 1 wherein the thermotropic liquid crystalline polyimide resin is selected from the group consisting of poly(2-methylpentyl pyromellitimide), poly(hexyl pyromellitimide), poly(octyl pentyl pyromellitimide), poly(dodecyl pentyl pyromellitimide), poly(trimethylhexyl pyromellitimide), poly(diethoxy pyromellitimide), poly(triethoxy pyromellitimide), poly(diisopropoxy pyromellitimide), poly(trisopropoxy pyromellitimide), poly(tetraisopropoxy pyromellitimide), poly(pentisopropoxy pyromellitimide), poly(dodecyl pyromellitimide), poly(2-methylpentyl bicyclo[2.2.2]oct-7-ene-2,3,5,6-diimide), poly(dodecyl bicyclo[2.2.2]oct-7-ene-2,3,5,6-diimide), poly(polyisopropoxy bicyclo[2.2.2]oct-7-ene-2,3,5,6-diimide), poly(polyisopropoxy 1,2,4,5-cyclohexanediimide), poly(2-methylpentyl 1,2,4,5-cyclohexanediimide), poly(dodecyl 1,2,4,5-cyclohexanediimide), poly(dioxypropylene-pyromellitimide), poly(dioxypropylene-pyromellitimide), and mixtures thereof. ### Claim 7 (depends on 1) A toner in accordance with claim 1 wherein the thermotropic liquid crystalline polyimide has a M.sub.n of from about 1,500 to about 20,000, and an M.sub.w of from about 2,500 to about 100,000. ### Claim 8 (depends on 1) A toner in accordance with claim 1 which possesses a low fixing temperature of from about 120.degree. C. to about 145.degree. C. and a broad fusing latitude of from about 40.degree. C. to about 120.degree. C. ### Claim 9 (depends on 1) A toner in accordance with claim 1 wherein the thermotropic liquid crystalline polyimide is obtained from the reaction of from about 0.40 mole equivalent to about 0.55 mole equivalent of a dianhydride, from about 0.40 mole equivalent to about 0.55 mole equivalent of a diamine, and optionally of from about 0.05 mole equivalent to about 0.2 mole equivalent of a kinking nonsymmetrical monomer. ### Claim 10 (depends on 9) A toner in accordance with claim 9 wherein the dianhydride is selected from the group consisting of pyromellitic dianhydride, pyromellitic tetracarboxylic acid, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic acid, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, and 5-(2,5-dioxotetrahydrol)-3-methyl-3-cyclohexene-1,2-dicarboxylic dianhydride. ### Claim 11 (depends on 9) A toner in accordance with claim 9 wherein the diamine selected from the group consisting of diaminoethane, diaminopropane, 2,3-diaminopropane, diaminobutane, diaminopentane, diamino-2-methylpentane diaminohexane, diaminotrimethylhexane, diaminoheptane, diaminooctane, diaminononane, diaminodecane, diaminododecane, diaminoterminated diethyleneoxide, diaminoterminated triethyleneoxide, and a polyoxyalkylene of the formula ##STR12## wherein R represents a hydrogen or alkyl group; and n represents the number of monomer segments, and is a number of from about 1 to about 10. ### Claim 12 (depends on 9) A toner in accordance with claim 9 wherein the kinking monomer is selected from the group consisting of 1,3-diaminocyclohexane, 2,4-toluene diamine, p-phenylene diamine, 2,2'-bis(4-aminophenyl) hexafluoropropane, 2,2-bis(3-amino-4-methylphenyl) hexafluoropropane, 2,2-bis(3-amino-4-hydroxy-phenyl) hexafluoropropane, 3,3'-diamino-4,4'-dihydroxy-biphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,4'-oxydianiline, 3,3-diamino-diphenylsulfone, 9,9-bis(4-aminophenyl) fluorene, and mixtures thereof; and n is a number of from about 1 to about 0.3 mole equivalent of the polyimide resin. ### Claim 13 (depends on 1) A toner composition in accordance with claim 1 with a glass transition temperature thereof of from about 50.degree. C. to about 65.degree. C. ### Claim 14 (depends on 1) A toner composition in accordance with claim 1 with a relative humidity sensitivity of from about 1.01 to about 2.3. ### Claim 15 (depends on 1) A toner composition in accordance with claim 1 further including a charge enhancing additive incorporated into the toner, or present on the surface of the toner. ### Claim 16 (depends on 1) A toner composition in accordance with claim 1 further containing a wax component with a weight average molecular weight of from about 1,000 to about 10,000. ### Claim 17 (depends on 1) A toner composition in accordance with claim 1 further containing as external additives metal salts of a fatty acid, colloidal silicas, or mixtures thereof. ### Claim 18 (depends on 1) A toner composition in accordance with claim 1 wherein the pigment is carbon black, magnetites, or mixtures thereof, cyan, magenta, yellow, red, blue, green, brown, or mixtures thereof. ### Claim 19 (depends on 1) A developer composition comprised of the toner composition of claim 1 and carrier particles. ### Claim 20 (depends on 19) A developer composition in accordance with claim 19 wherein the carrier particles are ferrites, steel, or an iron powder with an optional coating. ### Claim 21 (depends on 1) A method of imaging which comprises formulating an electrostatic latent image on a negatively charged photoreceptor, affecting development thereof with the toner composition of claim 1, and thereafter transferring the developed image to a suitable substrate. ### Claim 22 (depends on 1) A toner in accordance with claim 1 wherein m is a number of from about 10 to about 10,000. ### Claim 23 (depends on 1) A toner in accordance with claim 1 wherein m is a number of from about 10 to about 100, and oxalkylene and polyoxyalkylene contain from about 1 to about 15 carbon atoms.