Sustainable toners

• US 8,765,345 B2
• Filed: 11/07/2012
• Issued: 07/01/2014
• Est. Priority Date: 10/25/2011
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Zhou, Ke, Sacripante, Guerino G., Wang, Yulin, D'Amato, Michael
• Primary Examiner(s): LE, HOA VAN
• Application Number:
  US13/670,879
• Publication Number:
  US 20140127621A1
• Time in Patent Office: 601 Days
• Field of Search: 430/109.4, 527/600, 527/604, 528/306
• US Class Current: 430/109.4
• CPC Class Codes: B32B 5/16 characterised by features of a layer formed of particles, e.g. chips, powder or granules layer formed of natural mineral particles B32B19/00; layer being formed of wood fibres, chips or particles B32B21/02
• CPC Class Codes: C08G 63/553 Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
• 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 9/08791 characterised by the presence of specified groups or side chains
• 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
• CPC Class Codes: Y10T 428/2982 Particulate matter [e.g., sphere, flake, etc.]

Abstract

Disclosed is a polyester resin containing the polycondensation product of (a) at least one diacid, acid ester, or diester, and (b) at least two diols. The at least two diols include a disproportionated rosin diol and 2,2-bis(4-hydroxyphenyl)propane. Also disclosed is a toner composition having particles which include the disclosed polyester resin. Further disclosed is a method of preparing the disclosed polyester resin, and a method of forming toner particles that includes the disclosed polyester resin.

Claims

1. A polyester resin comprising a polycondensation product of:

(a) at least one compound selected from the group consisting of diacids, acid esters, and diesters; and

(b) at least two diols;

wherein the at least two diols comprise a disproportionated rosin diol and 2,2-bis(4-hydroxyphenyl)propane.

2. The polyester resin according to claim 1, wherein the disproportionated rosin diol is derived from a disproportionated distilled rosin acid.

3. The polyester resin according to claim 2, wherein the disproportionated distilled rosin acid has an acid value of from about 176 mg KOH to about 180 mg KOH.

4. The polyester resin according to claim 2, wherein the disproportionated distilled rosin acid is obtained by disproportionation and distillation of a crude rosin acid.

5. The polyester resin according to claim 1, wherein the disproportionated rosin diol is derived from a rosin acid and glycerine carbonate.

6. The polyester resin according to claim 1, wherein the polyester resin has a glass transition temperature of from about 50°

C. to about 65°

C.

7. The polyester resin according to claim 1, wherein the polyester resin has a softening point temperature of from about 110°

C. to about 130°

C.

8. The polyester resin according to claim 1, wherein the polyester resin has an acid value of from about 5 mg KOH/g to about 30 mg KOH/g.

9. The polyester resin according to claim 1, wherein the polyester resin has a polydispersity index (Mw/Mn) of from about 3 to about 100.

10. The polyester resin according to claim 1, wherein the at least one compound selected from the group consisting of diacids, acid esters, and diesters is selected from the group consisting of succinic acid, sebacic acid, and isophthalic acid.

11. A toner composition comprising toner particles comprising:

a polyester resin comprising the polycondensation product of;

(a) at least one compound selected from the group consisting of diacids, acid esters, and diesters; and

(b) at least two diols;

wherein

the at least two diols comprise a rosin diol and 2,2-bis(4-hydroxyphenyl)propane.

12. The toner composition according to claim 11, wherein the polyester resin is amorphous.

13. The toner composition according to claim 12, further comprising a crystalline polyester resin.

14. The toner composition according to claim 11, wherein the toner particles have a particle size of from about 3 μ

m to about 20 μ

m.

15. The toner composition according to claim 11, wherein the toner particles have a circularity of from about 0.93 to about 0.99.

16. The toner composition according to claim 11, wherein the at least one compound selected from the group consisting of diacids, acid esters, and diesters is selected from the group consisting of succinic acid, sebacic acid, and isophthalic acid.

17. The toner composition according to claim 11, wherein a heat cohesion of the toner composition at a temperature of from about 50°

C. to about 55°

C. is from 0 to about 20 weight percent.

18. A method of preparing a polyester resin, the method comprising polycondensing

(a) at least one compound selected from the group consisting of diacids, acid esters, and diesters;

and

(b) at least two diols;

wherein the at least two diols comprise a rosin diol and 2,2-bis(4-hydroxyphenyl)propane.

19. The method according to claim 18, wherein the rosin diol is synthesized from a rosin acid and glycerine carbonate.

20. The method according to claim 19, wherein the rosin acid is obtained by disproportionation and distillation of a crude rosin acid, and the rosin acid has an acid value of from about 176 mg KOH to about 180 mg KOH.