Super low melt toner having small molecule plasticizers

A method for making emulsion aggregation toner particles comprising:

• admixing polymeric amorphous resin emulsion, optionally at least one colorant emulsion, an optional wax emulsion, and a small molecule crystalline organic compound emulsion, the small molecule crystalline organic compound being selected from the group consisting of small molecule crystalline aromatic ethers having the formula
• wherein R1 and R2 are independently selected from the group consisting of an alkyl group, an arylalkyl group, an alkylaryl group, and an aromatic group, wherein at least one of R1 and R2 is an aromatic group, and wherein p is 0 or 1;
• and
• adding an aggregating agent to the composite emulsion to form emulsion aggregation toner particles;
• wherein a mixture of the amorphous resin and the small molecule crystalline organic compound is characterized by a reduction in glass transition temperature from that of the polymeric amorphous resin and by the lack of a significant solid to liquid phase transition peak for the small molecule crystalline organic compound as determined by differential scanning calorimetry, the enthalpy of fusion for the small molecule crystalline organic compound in the mixture being measured to be less than 10% of the enthalpy of fusion of the small molecule crystalline organic compound in pure form.

An emulsion aggregation (EA) toner comprising,

• an amorphous polymeric resin;
• optionally a colorant;
• and
• a small molecule crystalline organic compound being selected from the group consisting of small molecule crystalline monoesters having the formula:
• wherein R1 and R2 are aromatic groups;
• wherein a mixture of the amorphous polymeric resin and the small molecule crystalline organic compound is characterized by a reduction in glass transition temperature from that of the amorphous polymeric resin and by the lack of a significant solid to liquid phase transition peak for the small molecule crystalline organic compound as determined by differential scanning calorimetry, the enthalpy of fusion for the small molecule crystalline organic compound in the mixture being measured to be less than 10% of the enthalpy of fusion of the small molecule crystalline organic compound in pure form.