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

Claim 2

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.]..

Claim 3

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.

Claim 4

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.]..

Claim 5

A toner composition in accordance with claim 1 wherein the organic sulfonate compound is stearyl dimethyl benzyl ammonium para-toluene sulfonate. .[.

Claim 6

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..].

Claim 7

. A toner composition in accordance with claim 1 wherein the organic sulfonate compound is stearyl dimethyl phenethyl ammonium paratoluene

Claim 8

sulfonate. 8. A toner composition in accordance with claim 1 wherein the organic sulfonate material is cetyl diethyl benzyl ammonium para-toluene

Claim 9

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

Claim 10

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

Claim 11

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

Claim 12

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..].

Claim 13

A method of imaging in accordance with claim 9 wherein the charge control agent is stearyl dimethyl phenethyl ammonium para-toluene

Claim 14

sulfonate. 15. A method of imaging in accordance with claim 9 wherein the charge control agent is cetyl diethyl benzyl ammonium para-toluene

Claim 15

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

Claim 16

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

Claim 17

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

Claim 18

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.

Claim 19

. A developer composition in accordance with claim 17 wherein from about

Claim 20

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

Claim 21

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

Claim 22

phenthyl ammonium methyl sulfate..]. 24. A developer composition in accordance with claim 17 wherein the organic sulfonate compound is stearyl

Claim 23

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

Claim 24

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

Claim 25

fluoride hexafluoropropylene copolymer resin. 27. A developer composition in accordance with claims 1 or 17 wherein the resin is a styrene acrylate

Claim 26

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

Claim 27

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

Claim 28

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

Claim 29

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

Claim 30

of styrene, and 42 percent by weight of n-butylmethacrylate. 32. A developer composition in accordance with claims 1 or 17 wherein the

Claim 31

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.

Claim 32

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.

Claim 33

.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

Claim 34

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.

Claim 35

.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

Claim 36

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.