Bio-based amorphous polyester resins for emulsion aggregation toners

• US 8,163,459 B2
• Filed: 03/01/2010
• Issued: 04/24/2012
• Est. Priority Date: 03/01/2010
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Farrugia, Valerie M., Sacripante, Guerino, Zhou, Ke, Zwartz, Edward G., Hawkins, Michael S.
• Primary Examiner(s): LE, HOA VAN
• Application Number:
  US12/714,677
• Publication Number:
  US 20110212396A1
• Time in Patent Office: 785 Days
• Field of Search: 525/18, 430/137.14
• US Class Current: 430/137.14
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08G 63/85 Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof C08G63/823 takes precedence
• CPC Class Codes: G03G 9/0804 whereby the components are brought together in a liquid dispersing medium
• CPC Class Codes: G03G 9/0819 characterised by the dimensions of the particles
• CPC Class Codes: G03G 9/0827 characterised by their shape, e.g. degree of sphericity
• CPC Class Codes: G03G 9/08755 Polyesters
• CPC Class Codes: G03G 9/08795 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
• CPC Class Codes: G03G 9/08797 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature

Abstract

Disclosed are amorphous polyesters that contain only renewable resources designed for emulsion aggregation toner fabrication. The amorphous polyesters may be obtained from the mixture of three different monomers: 1,4:3,6-dianhydro-D-sorbitol (isosorbide), nonanedioic acid (azelaic acid), and butanedioic acid (succinic acid). Different polymer properties may be achieved depending on the ratio of these three monomers. By altering the ratio, polymers of high to low acid value can be obtained, as well as different ranges of glass transition temperatures.

Claims

1. A method of making an amorphous polyester resin, the method comprising:

synthesizing isosorbide from D-glucose;

obtaining a mixture comprising a succinic acid obtained by a submerged culture anaerobic fermentation process, and an azelaic acid produced by oxidative cleavage of oleic acid with chromic acid or by ozonolysis; and

polycondensing the isosorbide synthesized from D-glucose with the mixture of succinic acid and azelaic acid in the presence of a catalyst to obtain the amorphous polyester resin;

wherein;

the ratio of isosorbide to the mixture of succinic acid and azelaic acid in the polyester resin is from about 40;

60 to about 60;

40 mol % of the polyester resin;

the succinic acid is present in an amount of from about 30 to about 60 mol % of the polyester resin;

the azelaic acid is present in an amount of from about 5 to about 20 mol % of the polyester resin; and

a total amount of succinic acid and azelaic acid present in the polyester resin is from about 40 to 60 mol %.

2. The method of claim 1, wherein the polyester resin has a glass transition temperature of from about 30°

C. to about 120°

C.

3. The method of claim 1, wherein the polyester resin has a softening point temperature of from about 90°

C. to about 150°

C.

4. The method of claim 1, wherein the polyester resin has an acid value from about 2 to about 30 mgKOH/g.

5. A method of forming toner particles, the method comprising:

forming a slurry by mixing together;

an emulsion containing an amorphous polyester resin obtained from a method comprising;

synthesizing isosorbide from D-glucose;

obtaining a mixture comprising a succinic acid obtained by a submerged culture anaerobic fermentation process, and an azelaic acid produced by oxidative cleavage of oleic acid with chromic acid or by ozonolysis; and

polycondensing the isosorbide synthesized from D-glucose with the mixture of succinic acid and azelaic acid in the presence of a catalyst to obtain the amorphous polyester resin;

optionally a wax;

optionally a colorant;

optionally a surfactant;

optional a coagulant; and

one or more additional optional additives;

heating the slurry to form aggregated particles in the slurry;

freezing aggregation of the particles by adjusting the pH; and

heating the aggregated particles in the slurry to coalesce the particles into toner particles;

wherein;

the ratio of isosorbide to the mixture of succinic acid and azelaic acid in the polyester resin is from about 40;

60 to about 60;

40 mol % of the polyester resin;

the succinic acid is present in an amount of from about 30 to about 60 mol % of the polyester resin;

the azelaic acid is present in an amount of from about 5 to about 20 mol % of the polyester resin; and

a total amount of succinic acid and azelaic acid present in the polyester resin is from about 40 to 60 mol %.

6. The method of claim 5, wherein the polyester resin has a glass transition temperature of from about 45°

C. to about 75°

C.

7. The method of claim 5, wherein the polyester resin has a softening point temperature of from about 95°

C. to about 125°

C.

8. The method of claim 5, wherein the polyester resin has an acid value from about 5 to about 30 mgKOH/g.

9. The method of claim 5, wherein the toner particles have a circularity of from about 0.920 to about 0.999.

10. The method of claim 5, wherein the toner particles have a volume average diameter of from about 3 to about 25 μ

m.