Rosin-based resin and toner containing same

• US 8,580,472 B2
• Filed: 05/16/2011
• Issued: 11/12/2013
• Est. Priority Date: 01/17/2011
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Zhou, Ke, Sacripante, Guerino G, Carlini, Rina, Farrugia, Valerie M, Gerroir, Paul J
• Primary Examiner(s): RODEE, CHRISTOPHER D
• Application Number:
  US13/108,166
• Publication Number:
  US 20120183897A1
• Time in Patent Office: 911 Days
• Field of Search: 430/109.4, 528/306, 527/600, 527/604
• US Class Current: 430/109.4
• CPC Class Codes: C08G 63/553 Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
• CPC Class Codes: G03G 9/0804 whereby the components are brought together in a liquid dispersing medium
• CPC Class Codes: G03G 9/08755 Polyesters
• CPC Class Codes: G03G 9/08775 Natural macromolecular compounds or derivatives thereof
• CPC Class Codes: G03G 9/08797 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature

Abstract

Disclosed is a polyester resin comprising the polycondensation product of (a) at least one diacid, acid ester, or diester; and (b) at least one diol; wherein either (i) at least one diacid, acid ester, or diester comprises a rosin diacid, rosin acid ester, or rosin diester; or (ii) at least one diol comprises a rosin diol, and wherein at least one of the rosin diacid, rosin acid ester, rosin diester, or rosin diol is either (A) an ester of a functionalized rosin or an ester of a reduced functionalized rosin, or (B) a dimerized rosin. Also disclosed is a toner composition comprising particles which comprise the disclosed polyester resin and an optional colorant.

Claims

1. A polyester resin comprising the polycondensation product of:

(a) at least one diacid, acid ester, or diester; and

(b) at least one first diol which is a C36 dimer diol, isosorbide, or mixtures thereof;

wherein either

(i) at least one diacid, acid ester, or diester comprises a rosin diacid, rosin acid ester, or rosin diester;

or

(ii) at least one second diol comprises a rosin diol; and

wherein at least one of the rosin diacid, rosin acid ester, rosin diester, or rosin diol is either

(A) an ester of a functionalized rosin or an ester of a reduced functionalized rosin;

or

(B) a dimerized rosin.

2. A polyester resin according to claim 1 wherein at least one diacid, acid ester, or diester comprises a rosin diacid, rosin acid ester, or rosin diester.

3. A polyester resin according to claim 2 wherein the rosin diacid, acid ester, or diester is the reaction product of (A) abietic acid, neoabietic acid, palustric acid, pimaric acid, levo-pimaric acid, isopimaric acid, dehydroabietic acid, sandaracopimaric acid, or a mixture thereof;

with (B) acrylic acid, maleic acid, fumaric acid, itaconic acid, or a mixture thereof.

4. A polyester resin according to claim 1 wherein the ester of a functionalized rosin or ester of a reduced functionalized rosin is of the formula

5. A polyester resin according to claim 1 wherein the dimerized rosin is of the formula

6. A polyester resin according to claim 1 wherein the ester of a functionalized rosin or ester of a reduced functionalized rosin is of the formula

7. A toner composition comprising particles which comprise:

(1) a polyester resin; and

(2) an optional colorant.

8. A toner composition according to claim 7 wherein the polyester resin is amorphous.

9. A toner composition according to claim 8 further comprising a crystalline polyester resin.

10. A toner composition according to claim 9 wherein the crystalline polyester resin is (A) of the formula

11. A toner composition according to claim 7 wherein:

(a) the particles have a volume average diameter of at least about 3 μ

m;

(b) the particles have a volume average diameter of no more than about 12 μ

m; and

(c) the particles have a particle size distribution of no more than about 1.35.

12. A toner composition according to claim 7 wherein the toner is an emulsion aggregation toner.

13. A toner composition according to claim 7 having a core-shell structure.

14. A toner composition according to claim 7 wherein the ester of a functionalized rosin or ester of a reduced functionalized rosin is of the formula

15. A toner composition according to claim 7 wherein the ester of a functionalized rosin or ester of a reduced functionalized rosin is of the formula

16. A polyester resin comprising the polycondensation product of:

(a) at least one diacid, acid ester, or diester; and

(b) at least one diol;

wherein

(i) at least one diacid, acid ester, or diester comprises a rosin diacid, rosin acid ester, or rosin diester; and

(ii) at least one diol comprises a rosin diol; and

wherein at least one of the rosin diacid, rosin acid ester, rosin diester, or rosin diol is either

(A) an ester of a functionalized rosin or an ester of a reduced functionalized rosin;

or

(B) a dimerized rosin.

17. A polyester resin comprising the polycondensation product of:

(a) at least one diacid, acid ester, or diester; and

(b) at least one diol;

wherein at least one diol comprises a rosin diol; and

wherein at least one of the rosin diacid, rosin acid ester, rosin diester, or rosin diol is either

(A) an ester of a functionalized rosin or an ester of a reduced functionalized rosin;

or

(B) a dimerized rosin.

18. A polyester resin according to claim 17, wherein at least one diol is 1,2-propanediol, 1,3-propanediol, propylene glycol, dimer diol, isosorbide, or mixtures thereof.

19. A toner composition comprising particles which comprise:

(1) a polyester resin according to claim 17; and

(2) an optional colorant.