Toner Comprising Charge Control Agent

A developer comprising:

• an emulsion aggregation toner particle, and a toner carrier;
• wherein the emulsion aggregation toner particle comprises:
• at least one resin;
• an optional colorant;
• an optional wax;
• and a charge control agent disposed on a surface of the toner particle;
• wherein the charge control agent comprises a complex formed from a metal ion donor and at least one of a ligand selected from a member of the group consisting of a polyaromatic acid comprising humic acid, a pyranone based ligand, a furanone based ligand, or a combination thereof;
• and
• optionally, wherein the toner particle further comprises a surface additive disposed on a surface of the toner particle shell, wherein the surface additive is selected from a member of the group consisting of fumed silica, colloidal silica, polydimethylsiloxane treated silica, strontium titanate, cerium oxide, titanium dioxide, polydimethylsiloxane treated titanium dioxide, and combinations thereof.

An emulsion aggregation toner process comprising:

• obtaining a latex of at least one resin;
• optionally, obtaining an aqueous dispersion of an optional colorant;
• optionally, obtaining an aqueous dispersion of an optional wax;
• forming a mixture of the latex of at least one resin, the aqueous dispersion of the optional colorant, and the aqueous dispersion of the optional wax;
• heating the mixture to a first temperature;
• maintaining the first temperature to form aggregated toner particles;
• adding a latex of shell resin to form a shell over the aggregated particles;
• optionally, adding a solution of a chelating agent;
• stopping further aggregation and raising the temperature to a second temperature that is higher than the first temperature to coalesce the aggregated particles;
• cooling, optionally washing, optionally drying, and recovering the emulsion aggregation toner particles;
• precipitating a charge control agent onto a surface of the emulsion aggregation toner particles by adding a metal ion donor and at least one of a ligand selected from a member of the group consisting of a polyaromatic acid comprising humic acid, a pyranone based ligand, a furanone based ligand, or a combination thereof, to the emulsion aggregation toner particles, wherein the metal ion donor and polyaromatic acid comprising humic acid ligand, pyranone based ligand, furanone based ligand, or combination thereof, form the charge control agent, forming emulsion aggregation toner particles containing the internal charge control agent;
• and
• optionally, disposing a surface additive on a surface of the toner particle shell, wherein the surface additive is selected from a member of the group consisting of fumed silica, colloidal silica, polydimethylsiloxane treated silica, strontium titanate, cerium oxide, titanium dioxide, polydimethylsiloxane treated titanium dioxide, and combinations thereof.