Toner comprising reactive charge control agent

1. An emulsion aggregation toner comprising:

a toner particle comprising at least one resin; an optional colorant; an optional wax; and

a reactive charge control agent disposed on a surface of the toner particle;

wherein the reactive charge control agent comprises at least one positive charging compound, wherein the at least one positive charging compound comprises a member selected from the group consisting of an amine compound having at least 3 carbon atoms, an ammonium compound having at least 3 carbon atoms, a phosphonium compound having at least 3 carbon atoms, a boronium compound having at least 3 carbon atoms, and combinations thereof; at least one reactive anchoring compound, wherein the at least one reactive anchoring compound comprises a member selected the group consisting of amino, epoxy, carboxylic, hydroxyl, silanol, cyanide, anhydride, aldehyde, ketone, vinyl, and combinations thereof; and wherein the charge control agent optionally further comprises a negative charging compound, wherein the negative charging compound comprises a member selected from the group consisting of aromatic carboxylic acid, silanol, phenol, pyranone, furanone, and combinations thereof;

wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, aminopropyl-silsesquioxane, and combinations thereof.

2. The emulsion aggregation toner of claim 1 , wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, and combinations thereof.

3. The emulsion aggregation toner of claim 1 , wherein the reactive charge control agent comprises aminopropyl-silsesquioxane.

4. The emulsion aggregation toner of claim 1 , wherein the positive charging compound is selected from a member of the group consisting of an aromatic amine compound, an aromatic ammonium compound, an aromatic phosphonium compound, an alkyl amine compound having at least 3 to about 50 carbon atoms, an alkyl ammonium compound having at least 3 to about 50 carbon atoms, an alkyl phosphonium compound having at least 3 to about 50 carbon atoms, an alkyl boronium compound having at least 3 to about 50 carbon atoms, and combinations thereof.

5. The emulsion aggregation toner of claim 1 , wherein the toner particle comprises a core shell structure; and

wherein the reactive charge control agent is disposed on a surface of the toner particle shell.

6. The emulsion aggregation toner of claim 1 , wherein the toner is free of TiO 2 .

7. 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 reactive charge control agent disposed on a surface of the toner particle;

wherein the reactive charge control agent comprises at least one positive charging compound, wherein the at least one positive charging compound comprises a member selected from the group consisting of an amine compound having at least 3 carbon atoms, an ammonium compound having at least 3 carbon atoms, a phosphonium compound having at least 3 carbon atoms, a boronium compound having at least 3 carbon atoms, and combinations thereof; at least one reactive anchoring compound, wherein the at least one reactive anchoring compound comprises a member selected the group consisting of amino, epoxy, carboxylic, hydroxyl, silanol, cyanide, anhydride, aldehyde, ketone, vinyl, and combinations thereof; and wherein the charge control agent optionally further comprises a negative charging compound, wherein the negative charging compound comprises a member selected from the group consisting of aromatic carboxylic acid, silanol, phenol, pyranone, furanone, and combinations thereof-;

wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, aminopropyl-silsesquioxane, and combinations thereof.

8. The developer of claim 7 , wherein the toner particle comprises a core shell structure; and

wherein the reactive charge control agent is disposed on a surface of the toner particle shell.

9. The developer of claim 7 , wherein the charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, and combinations thereof.

10. The developer of claim 7 , wherein the charge control agent comprises aminopropyl-silsesquioxane.

11. The developer of claim 7 , wherein the positive charging compound is selected from a member of the group consisting of an aromatic amine compound, an aromatic ammonium compound, an aromatic phosphonium compound, an alkyl amine compound having at least 3 to about 50 carbon atoms, an alkyl ammonium compound having at least 3 to about 50 carbon atoms, an alkyl phosphonium compound having at least 3 to about 50 carbon atoms, an alkyl boronium compound having at least 3 to about 50 carbon atoms, and combinations thereof.

12. The developer of claim 7 , wherein the toner particle is free of TiO 2 .

13. An emulsion aggregation toner comprising:

a toner particle comprising at least one resin; an optional colorant; an optional wax; and

a reactive charge control agent disposed on a surface of the toner particle;

wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, aminopropyl-silsesquioxane, aminopropyl/methylsilsesquioxane, and combinations thereof.

14. 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 reactive charge control agent disposed on a surface of the toner particle;

wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, aminopropyl-silsesquioxane, aminopropyl/methylsilsesquioxane, and combinations thereof.

15. An emulsion aggregation toner process comprising:

obtaining a latex of at least one resin;

obtaining an aqueous dispersion of a colorant;

obtaining an aqueous dispersion of a wax;

forming a mixture of the latex of at least one resin, the aqueous dispersion of the colorant, and the aqueous dispersion of the 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 forming emulsion aggregation toner particles;

cooling, optionally washing, optionally drying, and recovering the emulsion aggregation toner particles;

introducing a reactive charge control agent to the emulsion aggregation toner particles, forming emulsion aggregation toner particles containing the reactive charge control agent; wherein the reactive charge control agent comprises at least one positive charging compound, wherein the at least one positive charging compound comprises a member selected from the group consisting of an amine compound having at least 3 carbon atoms, an ammonium compound having at least 3 carbon atoms, a phosphonium compound having at least 3 carbon atoms, a boronium compound having at least 3 carbon atoms, and combinations thereof; at least one reactive anchoring compound, wherein the at least one reactive anchoring compound comprises a member selected the group consisting of amino, epoxy, carboxylic, hydroxyl, silanol, cyanide, anhydride, aldehyde, ketone, vinyl, and combinations thereof; and wherein the charge control agent optionally further comprises a negative charging compound, wherein the negative charging compound comprises a member selected from the group consisting of aromatic carboxylic acid, silanol, phenol, pyranone, furanone, and combinations thereof

wherein the reactive charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, aminopropyl-silsesquioxane, and combinations thereof.

16. The emulsion aggregation toner process of claim 15 , further comprising:

combining the emulsion aggregation toner particles with a toner carrier to form a developer.

17. The emulsion aggregation toner process of claim 15 , wherein the charge control agent comprises a member of the group consisting of phenylsilane, amino-silsesquioxane, and combinations thereof.

18. The emulsion aggregation toner process of claim 15 , wherein the charge control agent comprises aminopropyl-silsesquioxane.

19. The emulsion aggregation toner process of claim 15 , wherein the toner particle is free of TiO 2 .