Quarternary ammonium sulfate or sulfonate charge control agents for electrophotographic developers compatible with viton fuser

Abstract

This invention is directed to a dry electrostatic toner composition containing a resin, a colorant or pigment, and an organic sulfate or sulfonate charge control additive of the following formula: ##STR1## wherein R 1 is an alkyl radical containing from about 12 carbon atoms to about 22 carbon atoms, and preferably from about 14 carbon atoms to 18 carbon atoms, R 2 and R 3 are independently selected from alkyl groups containing from about 1 carbon atom to about 5 carbon atoms, R 4 is an alkylene group containing from about 1 carbon atom to about 5 carbon atoms, R 5 is a tolyl group or an alkyl group containing from about 1 carbon atom to about 3 carbon atoms and n is the number 3 or 4. Such toners, especially when combined with carrier materials, are useful for causing the development of images in an electrophotographic system.

What is claimed is: 
     
       1. A dry electrostatic toner composition comprised of toner particles containing resin particles and pigment particles, and .Iadd.dispersed therein as a charge enhancing additive .Iaddend.from about 0.1 to about 10 percent based on the weight of the toner particles of an organic .[.sulfate or.]. sulfonate composition of the following formula: ##STR5## wherein R 1  is an alkyl radical containing from about 12 carbon atoms to about 22 carbon atoms, R 2  and R 3  are independently selected from alkyl groups containing from about 1 carbon atom to about 5 carbon atoms, R 4  is an alkylene group containing from about 1 carbon atom to about 5 carbon atoms, R 5  is a tolyl group .[.or an alkyl group containing from about 1 carbon atom to about 3 carbon atoms.]. and n is the number 3 .[.or 4.].. 
     
     
       2. A toner composition in accordance with claim 1 wherein R 1  is an alkyl group containing from about 14 to about 18 carbon atoms, R 2 , R 3 , are alkyl groups having from 1 to about 5 carbon atoms, R 4  is an alkylene group, R 5  is a tolyl radical, and n is the number 3. 
     
     
       3. A toner composition in accordance with claim 1 wherein R 1  is stearyl, R 2 , R 3 , are methyl, .Iadd.and .Iaddend.R 4  is methylene or ethylene .[., R 5  is methyl, and n is the number 4.].. 
     
     
       4. A toner composition in accordance with claim 1 wherein the organic sulfonate compound is stearyl dimethyl benzyl ammonium para-toluene sulfonate. .[. 
     
     
       5.  A toner composition in accordance with claim 1 wherein the organic sulfate compound is stearyl dimethyl benzyl ammonium methyl sulfate..]. .[.6. A toner composition in accordance with claim 1 wherein the organic sulfate compound is stearyl dimethyl phenethyl ammonium methyl sulfate..]. 
     
     
        . A toner composition in accordance with claim 1 wherein the organic sulfonate compound is stearyl dimethyl phenethyl ammonium paratoluene 
     
     
        sulfonate. 8. A toner composition in accordance with claim 1 wherein the organic sulfonate material is cetyl diethyl benzyl ammonium para-toluene 
     
     
        sulfonate. 9. A method of imaging comprising forming a negative electrostatic latent image on a photoreceptor surface, contacting the resulting image with a developer composition comprised of positively charged toner particles and carrier particles, the toner particles being comprised of resin particles, pigment particles, and .Iadd.dispersed therein as a charge enhancing additive .Iaddend.from about 0.1 to about 10 weight percent based on the weight of the toner particles of an organic .[.sulfate or.]. sulfonate composition of the following formula: ##STR6## followed by subsequently transferring the developed latent image to a substrate, and permanently affixing the image thereto, wherein R 1  is .[.analkyl.]. .Iadd.an alkyl .Iaddend.radical containing from about 12 carbon atoms to about 22 carbon atoms, R 2  and R 3  are independently selected from alkyl groups containing from about 1 carbon atom to about 5 carbon atoms, R 4  is an alkylene group containing from about 1 carbon atom to about 5 carbon atoms, R 5  is tolyl group .[.or an alkyl group containing from about 1 carbon atom to about 3 carbon 
     
     
        atoms.]. and n is the number 3 .[.or 4.].. 10. A method of imaging in accordance with claim 9 wherein R 1  is an alkyl group containing from about 14 to about 18 carbon atoms, R 2 , R 3  are alkyl groups having from about 1 carbon atoms to about 5 carbon atoms, R 4  is an alkylene group containing 1 to 3 carbon atoms, R 5  is a tolyl and n is 
     
     
        the number 3. 11. A method of imaging in accordance with claim 9 wherein R 1  is stearyl, R 2 , R 3 , and R 5  are methyl, .Iadd.and .Iaddend.R 4  is methylene or ethylene .[.and n is the number 4.].. .[.12. A method of imaging in accordance with claim 9 wherein the charge control additive is stearyl dimethyl benzyl ammonium methyl sulfate..]. .[.13. A method of imaging in accordance with claim 9 wherein the charge control additive is stearyl dimethyl phenethyl ammonium methyl sulfate..]. 
     
     
        4. A method of imaging in accordance with claim 9 wherein the charge control agent is stearyl dimethyl phenethyl ammonium para-toluene 
     
     
        sulfonate. 15. A method of imaging in accordance with claim 9 wherein the charge control agent is cetyl diethyl benzyl ammonium para-toluene 
     
     
        sulfonate. 16. A method of imaging in accordance with claim 9 wherein there is used as the fusing mechanism a soft roll fuser wherein contamination and decomposition of the materials on the fuser roll are not 
     
     
        adversely affected. 17. A dry electrostatic developer composition comprised of toner particles and carrier particles, the toner particles being comprised of resin particles, and pigment particles, said developer composition further including .Iadd.dispersed in the toner particles as a charge enhancing additive .Iaddend.from about 0.1 to about 10 percent based on the weight of the toner particles of an organic .[.sulfate or.]. sulfonate composition of the following formula: ##STR7## wherein R 1  is an alkyl radical containing from about 12 carbon atoms to about 22 carbon atoms, R 2  and R 3  are independently selected from alkyl radicals containing from about 1 carbon atom to about 5 carbon atoms, R 4  is an alkylene group containing from about 1 carbon atom to about 5 carbon atoms, R 5  is a tolyl group .[.or an alkyl group containing from about 1 carbon atom to about 3 carbon atoms.]., and n is 
     
     
        the number 3 .[.or 4.].. 18. A developer composition in accordance with claim 17 wherein the carrier is comprised of a steel core coated with a perfluoralkoxy fluoropolymer resin, or with a vinylidene fluoride resin. 
     
     
          . A developer composition in accordance with claim 17 wherein from about 
     
     
        1 part of toner to 200 parts of carrier particles are employed. 20. A developer composition in accordance with claim 17 wherein R 1  is an alkyl group containing from about 14 carbon atoms to about 18 carbon atoms, R 3  are alkyl radicals having from 1 to about 5 carbon atoms, R 4  is an alkylene group, R 5  is a tolyl radical, and n is the 
     
     
        number 3. 21. A developer composition in accordance with claim 17 wherein the organic sulfonate compound is strearyl dimethyl benzyl ammonium paratoluene sulfonate. .[.22. A developer composition in accordance with claim 17 wherein the organic sulfate compound is stearyl dimethyl benzyl ammonium methyl sulfate..]. .[.23. A developer composition in accordance with claim 17 wherein the organic sulfate compound is stearyl dimethyl 
     
     
        phenthyl ammonium methyl sulfate..]. 24. A developer composition in accordance with claim 17 wherein the organic sulfonate compound is stearyl 
     
     
        dimethyl phenethyl ammonium para-toluene sulfonate. 25. A method of imaging in accordance with claim 9 wherein the image is permanently affixed to a substrate utilizing a fusing mechanism comprised of a soft 
     
     
        roll fuser. 26. A method of imaging in accordance with claim 25 wherein the soft roll fuser is comprised of lead oxide coated with a vinylidene 
     
     
        fluoride hexafluoropropylene copolymer resin. 27. A developer composition in accordance with claims 1 or 17 wherein the resin is a styrene acrylate 
     
     
        copolymer, or a styrene butadiene copolymer. 28. A developer composition in accordance with claim 27 wherein the styrene acrylate copolymer is a styrene butylmethacrylate copolymer, and the styrene butadiene copolymer comprises from about 80 percent to about 90 percent of styrene, and from 
     
     
        about 10 percent to about 20 percent of butadiene. 29. A developer composition in accordance with claim 28 wherein the styrene butylmethacrylate copolymer is a styrene n-butylmethacrylate copolymer comprised of from about 55 weight percent styrene to about 70 weight percent styrene, and from about 45 weight percent n-butylmethacrylate to 
     
     
        about 30 weight percent of n-butylmethacrylate. 30. A developer composition in accordance with claim 29 wherein the resin is comprised of a styrene n-butylmethacrylate copolymer resin containing 65 percent by 
     
     
        weight of styrene, and 35 percent by weight of n-butylmethacrylate. 31. A developer composition in accordance with claim 30 wherein the styrene n-butylmethacrylate copolymer resin is comprised of 58 percent by weight 
     
     
        of styrene, and 42 percent by weight of n-butylmethacrylate. 32. A developer composition in accordance with claims 1 or 17 wherein the 
     
     
        pigment is carbon black. .Iadd.33.  A two-component electrophotographic developer comprising magnetic carrier particles and a dry particulate electrophotographic toner comprising a major amount of binder polymer and dispersed therein as a charge control agent in an amount of from 0.1 to 10 weight percent of the particulate toner, a quaternary ammonium salt of the formula: ##STR8## wherein R is an alkyl group of 12 to 22 carbon atoms and X is the anion R 5  SO n  wherein R 5  is a tolyl group, and n is the number 3. 
     
     
        .Iaddend. .Iadd.34.  A developer according to claim 33 wherein the binder polymer also has a colorant dispersed therein and R is a straight chain alkyl of 14 to 18 carbon atoms and X is a 1 to about 3 carbon atom alkyl sulfonate ion, or a tolyl sulfonate ion. .Iaddend. .Iadd.35. A developer according to claim 34 wherein R is octadecyl. .Iaddend. .Iadd.36. A developer according to claim 34 wherein the binder polymer is a styrene 
     
     
        acrylic copolymer. .Iaddend. .Iadd.37.  A developer according to claim 36 wherein the binder polymer is cross-linked, styrene-butylacrylate copolymer and the colorant is a carbon black. .Iaddend. .Iadd.38. A developer according to claim 37 wherein the toner contains 0.5 to 5 parts by weight of said quaternary ammonium salt and about 6 parts by weight of carbon black per hundred parts of polymer. .Iaddend. .Iadd.39. An electrophotographic developer according to claim 38 comprising a mixture of ferromagnetic carrier particles coated with a fluorocarbon polymer and said particulate toner. .Iaddend. .Iadd.40. A two-component electrophotographic developer comprising magnetic carrier particles and a dry particulate electrophotographic toner comprising a major amount of binder polymer and dispersed therein as a charge control agent in an amount of from 0.1 to 10 weight percent of the particulate toner, a quaternary ammonium salt of the formula: ##STR9## wherein R is an alkyl group of 12 to 24 carbon atoms, and X is a 1 to about 3 carbon alkyl sulfonate ion or a tolyl sulfonate ion. .Iaddend. 
     
     
        .Iadd.41.  A developer according to claim 40, wherein R is an alkyl group of 14 to 18 carbon atoms. .Iaddend. .Iadd.42. A developer composition in accordance with claim 40 wherein the charge control agent is present in an amount of 0.1 to 3 weight percent. .Iaddend. .Iadd.43. A developer composition in accordance with claim 40 wherein the binder polymer has a colorant dispersed therein. .Iaddend. .Iadd.44. A dry electrostatic toner composition comprised of toner particles containing resin particles and pigment particles, and dispersed in the toner paticles from about 0.1 to about 10 percent based on the weight of the toner particles a charge enhancing additive selected from the group consisting of stearyl dimethyl benzyl ammonium paratoluene sulfonate and stearyl dimethyl phenethyl ammonium paratoluene sulfonate. .Iaddend. .Iadd.45. A toner composition in accordance with claim 44 wherein the pigment particles are carbon black. .Iaddend. .Iadd.46. A toner composition in accordance with claim 44 wherein the resin particles are selected from the group consisting of styrene acrylate copolymers and styrene butadiene copolymers. .Iaddend. .Iadd.47. A developer composition comprised of the toner composition of claim 44, and carrier particles. .Iaddend. .Iadd.48. A developer composition in accordance with claim 47 wherein the carrier is comprised 
     
     
        of a steel core. .Iaddend. .Iadd.49.  A developer composition in accordance with claim 47 wherein the developer contains thereover a polymeric coating. .Iaddend. .Iadd.50. A developer composition in accordance with claim 49 wherein the polymeric coating is a perfluoroalkoxy fluoropolymer resin or a vinylidene fluoride resin. .Iaddend. .Iadd.51. A dry electrostatic toner composition comprised of toner particles containing resin particles and pigment particles, and dispersed in the toner particles as a charge enhancing additive from about 0.1 to about 10 percent based on the weight of the toner particles stearyl dimethyl phenethyl ammonium methyl sulfate. .Iaddend. .Iadd.52. A toner composition in accordance with claim 51 wherein the pigment particles are carbon black. .Iaddend. .Iadd.53. A developer composition comprised of the toner composition of claim 51, and carrier particles. .Iaddend.