TONER PARTICLES HAVING A REDUCED CONTENT OF ARYL AMINES OR N-ARYLACETOACETAMIDES AND OXIDATION METHODS FOR PRODUCING THE SAME

1 . A method comprising:

providing toner particles comprising an N-arylacetoacetarylide pigment composition, the N-arylacetoacetarylide pigment composition comprising a diazonium coupling product of a first aryl amine and an N-arylacetoacetamide formed from a second aryl amine;

wherein the N-arylacetoacetarylide pigment composition comprises at least some residual N-arylacetoacetamide that has not undergone diazonium coupling and/or at least some residual second aryl amine that has not reacted to form the N-arylacetoacetamide and/or has hydrolyzed from the N-arylacetoacetamide; and

contacting the toner particles with an oxidant in an aqueous phase at a temperature and for a time sufficient to decrease a concentration of at least the residual second aryl amine in the toner particles.

2 . The method of claim 1 , wherein the toner particles are core-shell toner particles and/or are prepared by an emulsion aggregation-coalescence process.

3 . The method of claim 2 , wherein the toner particles are prepared by the emulsion aggregation-coalescence process and are contacted with the oxidant during at least a portion of a coalescence stage of the emulsion aggregation-coalescence process.

4 . The method of claim 3 , wherein the coalescence stage takes place at a temperature above a glass transition temperature of the toner particles.

5 . The method of claim 1 , wherein the toner particles are obtained as a toner slurry from a toner production process, and the toner slurry is contacted with the oxidant.

6 . The method of claim 1 , wherein the toner particles are isolated as a solid prior to being contacted with the oxidant.

7 . The method of claim 1 , wherein the oxidant comprises a persulfate salt, a hypochlorite salt, or any combination thereof.

8 . The method of claim 1 , wherein a hydroxide compound, a carbonate salt, a bicarbonate salt, or any combination thereof is present in combination with the oxidant.

9 . The method of claim 1 , wherein the oxidant comprises a persulfate salt, and the temperature is about 25° C. to about 95° C.

10 . The method of claim 9 , wherein the time is about 0.5 hours to about 24 hours.

11 . The method of claim 1 , wherein the oxidant comprises a hypochlorite salt, and the temperature is about 25° C. to about 50° C.

12 . The method of claim 1 , wherein the N-arylacetoacetarylide pigment composition comprises an N-arylacetoacetarylide selected from the group consisting of Pigment Yellow 17, Pigment Yellow 74, Pigment Yellow 83, Pigment Yellow 180, and any combination thereof.

13 . The method of claim 1 , wherein the second aryl amine is o-anisidine.

14 . The method of claim 1 , wherein the temperature and time are sufficient to decrease the concentration of the second aryl amine by at least about 70% on a mass basis relative to an amount of the second aryl amine in the toner particles.

15 . A toner composition comprising:

toner particles comprising an N-arylacetoacetarylide pigment composition, the N-arylacetoacetarylide pigment composition comprising a diazonium coupling product of a first aryl amine and an N-arylacetoacetamide formed from a second aryl amine;

wherein a concentration of residual second aryl amine in the toner particles is about 20 ppm or below.

16 . The toner composition of claim 15 , wherein the toner particles are core-shell toner particles and/or are prepared by an emulsion aggregation-coalescence process.

17 . The toner composition of claim 15 , wherein the N-arylacetoacetarylide pigment composition comprises an N-arylacetoacetarylide selected from the group consisting of Pigment Yellow 17, Pigment Yellow 74, Pigment Yellow 83, Pigment Yellow 180, and any combination thereof.

18 . The toner composition of claim 15 , wherein the second aryl amine is o-anisidine.