TONER COMPOSITION AND PROCESS

• US 20170248859A1
• Filed: 02/25/2016
• Published: 08/31/2017
• Est. Priority Date: 02/25/2016
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Sacripante, Guerino G., Nosella, Kimberly D., Pawlak, John Lawrence
• Granted Patent: US 9,760,032 B1
• Time in Patent Office: Days
• CPC Class Codes: G03G 9/0804 whereby the components are brought together in a liquid dispersing medium
• CPC Class Codes: G03G 9/081 by mixing the toner components in a liquefied state; melt kneading; reactive mixing
• CPC Class Codes: G03G 9/08755 Polyesters
• CPC Class Codes: G03G 9/08782 Waxes
• CPC Class Codes: G03G 9/08795 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
• CPC Class Codes: G03G 9/09321 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03G 9/09371 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03G 9/09378 Non-macromolecular organic compounds
• CPC Class Codes: G03G 9/09385 Inorganic compounds
• CPC Class Codes: G03G 9/09392 Preparation thereof

Abstract

A toner composition comprising (a) a first lower molecular weight amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof present in an amount of from about 5 to about 15 weight percent, based on the total weight of the first amorphous polyester; (b) a second higher molecular weight amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof, and a branching agent derived from a polyacid or polyol component; wherein the dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof is present in the second amorphous polyester in an amount of from about 5 to about 15 weight percent, based on the total weight of the second amorphous polyester; (c) a crystalline polyester resin; (d) a wax; and (e) optionally, a colorant.

Claims

1. A toner composition comprising:

(a) a first amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof;

wherein the first amorphous polyester is generated by the catalytic polymerization of monomers of an organic diol, an organic diacid, and dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof;

wherein the dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, is present in the first amorphous polyester in an amount of from about 5 to about 15 weight percent, based on the total weight of the first amorphous polyester;

(b) a second amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof, and a branching agent derived from a polyacid or polyol component;

wherein the second amorphous polyester is generated by the catalytic polymerization of monomers of an organic diol, an organic diacid, dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, and the branching agent;

wherein the dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof is present in the second amorphous polyester in an amount of from about 5 to about 15 weight percent, based on the total weight of the second amorphous polyester;

(c) a crystalline polyester resin;

(d) a wax; and

(e) optionally, a colorant.

2. The toner of claim 1, wherein the first amorphous polyester resin is a low molecular weight polyester having a molecular weight of from about 15,000 to about 25,000 grams per mole;

and

wherein the first amorphous polyester resin has a glass transition temperature of from about 55 to about 65°

C.

3. The toner of claim 1, wherein the first amorphous polyester resin comprises dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, in an amount of from about 9 to about 13 weight percent, based on the total weight of the first amorphous polyester.

4. The toner of claim 1, wherein the first amorphous polyester resin is selected from the group consisting of fumaric acid, terephthalic acid, dodecenyl succinic acid, dodecenyl succinic anhydride, propoxylated bisphenol A and ethoxylated bisphenol A.

5. The toner of claim 1, wherein the second amorphous polyester resin is a high molecular weight polyester having a molecular weight of from about 50,000 to about 150,000 grams per mole;

and

wherein the second amorphous polyester resin has a glass transition temperature of from about 52 to about 62°

C.

6. The toner of claim 1, wherein the second amorphous polyester resin comprises dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, in an amount of from about 9 to about 13 weight percent, based on the total weight of the second amorphous polyester.

7. The toner of claim 1, wherein the second amorphous polyester resin is generated with a branching agent selected from the group consisting of trimellitic acid, trimellitic anhydride, and glycerol.

8. The toner of claim 1, wherein the second amorphous polyester resin is selected from the group consisting of terephthalic acid, dodecenyl succinic acid, dodecenyl succinic anhydride, trimellitic acid, propoxylated bisphenol A and ethoxylated bisphenol A.

9. The toner of claim 1, wherein the crystalline polyester resin is selected from the group consisting of poly(1,2-propylene-diethylene-terephthalate), poly(ethylene-terephthalate), poly(propylene-terephthalate), poly(butylene-terephthalate), poly(pentylene-terephthalate), poly(hexylene-terephthalate), poly(heptylene-terephthalate), poly(octylene-terephthalate), poly(ethylene-sebacate) (10:

2), poly(propylene-sebacate) (10;

3), poly(butylene-sebacate) (10;

4), poly(hexylene-sebacate) (10;

6), poly(nonylene-sebacate) (10;

9), poly(decylene-sebacate) (10;

10), poly(dodecylene-sebacate) (10;

12), poly(ethylene-adipate) (6;

2), poly(propylene-adipate) (6;

3), poly(butylene-adipate) (6;

4), poly(pentylene-adipate) (6;

4), poly(hexylene-adipate) (6;

6), poly(heptylene-adipate) (6;

7), poly(octylene-adipate) (6;

8), poly(ethylene-glutarate) (5;

2), poly(propylene-glutarate) (5;

3), poly(butylene-glutarate) (5;

4), poly(pentylene-glutarate) (5;

5), poly(hexylene-glutarate) (5;

6), poly(heptylene-glutarate) (5;

7), poly(octylene-glutarate) 5;

8), poly(ethylene-pimelate) (7;

2), poly(propylene-pimelate) (7;

3), poly(butylene-pimelate) (7;

4), poly(pentylene-pimelate) (7;

5), poly(hexylene-pimelate) (7;

6), poly(heptylene-pimelate) (7;

7), poly(1,2-propylene itaconate), poly(ethylene-succinate) (4;

2), poly(propylene-succinate) (4;

3), poly(butylene-succinate) (4;

4), poly(pentylene-succinate) (4;

5), poly(hexylene-succinate) (4;

6), poly(octylene-succinate) (4;

8), poly(ethylene-dodecanoate) (12;

2), poly(propylene-dodecanoate) (12;

3), poly(butylene-dodecanoate) (12;

4), poly(pentylene-dodecanoate) (12;

5), poly(hexylene-dodecanoate) (12;

6), poly(nonylene-dodecanoate) (12;

9), poly(decylene-dodecanoate) (12;

10), poly(dodecylene-dodecanoate) (12;

12), copoly(ethylene-fumarate)-copoly(ethylene-sebacate), copoly(ethylene-fumarate)-copoly(ethylene-decanoate), copoly(ethylene-fumarate)-copoly(ethylene-dodecanoate), and mixtures thereof.

10. The toner of claim 1, wherein the crystalline polyester has an oligomer unit with a carbon to oxygen ratio of from about 3 to about 7.

11. The toner of claim 1, wherein the crystalline polyester has an oligomer unit having from about 12 to about 28 carbon atoms.

12. The toner of claim 1, wherein the first amorphous polyester resin comprises dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, in an amount of from about 9 to about 13 weight percent, based on the total weight of the first amorphous polyester;

wherein the second amorphous polyester resin comprises dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, in an amount of from about 9 to about 13 weight percent, based on the total weight of the second amorphous polyester; and

wherein the crystalline polyester has an oligomer unit with a carbon to oxygen ratio of from about 3 to about 7.

13. The toner of claim 1, wherein the wax is present in an amount of from about 2 to about 13 percent by weight, based on the total weight of the toner.

14. The toner of claim 1, wherein the wax is selected from the group consisting of polyethylene, polypropylene, and mixtures thereof.

15. The toner of claim 1, wherein the toner comprises a core and a shell disposed thereover;

wherein the core comprises the crystalline resin, the first and second amorphous polyester resin, the colorant, and the wax; and

wherein the shell comprises at least one of the first amorphous polyester, the second amorphous polyester, or a combination of both the first amorphous polyester and the second amorphous polyester.

16. A process comprising:

mixing

(a) a first amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof;

wherein the first amorphous polyester is generated by the catalytic polymerization of monomers of an organic diol, an organic diacid, and dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof;

wherein the dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, is present in the first amorphous polyester in an amount of from about 5 to about 15 weight percent, based on the total weight of the first amorphous polyester;

(b) a second amorphous polyester resin comprising a polyester derived from dodecenyl succinic acid, dodecenyl succinic anhydride, or a combination thereof, and a branching agent derived from a polyacid or polyol component;

wherein the second amorphous polyester is generated by the catalytic polymerization of monomers of an organic diol, an organic diacid, dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof, and the branching agent;

wherein the dodecenyl succinic acid, dodecenyl succinic anhydride, or combination thereof is present in the second amorphous polyester in an amount of from about 5 to about 15 weight percent, based on the total weight of the second amorphous polyester;

(c) a crystalline polyester resin;

(d) a wax; and

(e) optionally, a colorant;

aggregating; and

coalescing to form toner particles.

17. The process of claim 16, wherein the first amorphous polyester resin is a low molecular weight polyester having a molecular weight of from about 15,000 to about 25,000 grams per mole;

and

wherein the first amorphous polyester resin has a glass transition temperature of from about 55 to about 65°

C.

18. The process of claim 16, wherein the second amorphous polyester resin is a high molecular weight polyester having a molecular weight of from about 50,000 to about 150,000 grams per mole;

and

wherein the second amorphous polyester resin has a glass transition temperature of from about 55 to about 62°

C.

19. The process of claim 16, wherein the crystalline polyester resin is selected from the group consisting of poly(1,2-propylene-diethylene-terephthalate), poly(ethylene-terephthalate), poly(propylene-terephthalate), poly(butylene-terephthalate), poly(pentylene-terephthalate), poly(hexylene-terephthalate), poly(heptylene-terephthalate), poly(octylene-terephthalate), poly(ethylene-sebacate) (10:

2), poly(propylene-sebacate) (10;

3), poly(butylene-sebacate) (10;

4), poly(hexylene-sebacate) (10;

6), poly(nonylene-sebacate) (10;

9), poly(decylene-sebacate) (10;

10), poly(dodecylene-sebacate) (10;

12), poly(ethylene-adipate) (6;

2), poly(propylene-adipate) (6;

3), poly(butylene-adipate) (6;

4), poly(pentylene-adipate) (6;

4), poly(hexylene-adipate) (6;

6), poly(heptylene-adipate) (6;

7), poly(octylene-adipate) (6;

8), poly(ethylene-glutarate) (5;

2), poly(propylene-glutarate) (5;

3), poly(butylene-glutarate) (5;

4), poly(pentylene-glutarate) (5;

5), poly(hexylene-glutarate) (5;

6), poly(heptylene-glutarate) (5;

7), poly(octylene-glutarate) 5;

8), poly(ethylene-pimelate) (7;

2), poly(propylene-pimelate) (7;

3), poly(butylene-pimelate) (7;

4), poly(pentylene-pimelate) (7;

5), poly(hexylene-pimelate) (7;

6), poly(heptylene-pimelate) (7;

7), poly(1,2-propylene itaconate), poly(ethylene-succinate) (4;

2), poly(propylene-succinate) (4;

3), poly(butylene-succinate) (4;

4), poly(pentylene-succinate) (4;

5), poly(hexylene-succinate) (4;

6), poly(octylene-succinate) (4;

8), poly(ethylene-dodecanoate) (12;

2), poly(propylene-dodecanoate) (12;

3), poly(butylene-dodecanoate) (12;

4), poly(pentylene-dodecanoate) (12;

5), poly(hexylene-dodecanoate) (12;

6), poly(nonylene-dodecanoate) (12;

9), poly(decylene-dodecanoate) (12;

10), poly(dodecylene-dodecanoate) (12;

12), copoly(ethylene-fumarate)-copoly(ethylene-sebacate), copoly(ethylene-fumarate)-copoly(ethylene-decanoate), copoly(ethylene-fumarate)-copoly(ethylene-dodecanoate), and mixtures thereof.

20. The process of claim 16, wherein the crystalline polyester has an oligomer unit with a carbon to oxygen ratio of from about 3 to about 7.