Toner and method for producing toner

• US 10,078,281 B2
• Filed: 09/01/2017
• Issued: 09/18/2018
• Est. Priority Date: 09/06/2016
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Ida, Hayato, Tamura, Junichi, Murayama, Ryuji, Shibata, Takaho, Yamashita, Daisuke, Hirasa, Takashi
• Primary Examiner(s): Chapman, Mark A
• Application Number:
  US15/693,662
• Publication Number:
  US 20180067411A1
• Time in Patent Office: 382 Days
• Field of Search: 4301093
• CPC Class Codes: G03G 9/0806 whereby chemical synthesis of at least one of the toner components takes place
• CPC Class Codes: G03G 9/08706 Polymers of alkenyl-aromatic compounds
• CPC Class Codes: G03G 9/08724 Polyvinylesters
• CPC Class Codes: G03G 9/08737 Polymers derived from conjugated dienes
• CPC Class Codes: G03G 9/08793 Crosslinked polymers

Abstract

A toner having a toner particle containing a resin component, wherein the resin component contains an olefin copolymer having ester group and the like, which has a unit (1), and a unit Y2 that is at least one selected from (2) and (3), the content of the copolymer in the resin component is at least 50 mass % with respect to the total mass of the resin component, and the content of the monomer unit Y2 is 3 to 35 mass % with respect to the total mass of the copolymer;

• • in formulas (1) to (3), R¹, R² and R⁴ each independently represent H or CH₃, and R³ and R⁵ each independently represent CH₃ or C₂H₅.

Claims

1. A toner comprising a toner particle containing a resin component,

wherein

the resin component contains an olefin copolymer having ester group and a crosslinked body from an aliphatic hydrocarbon resin having unsaturated bond,

the olefin copolymer having ester group has:

a monomer unit Y1 represented by the following formula (1); and

a monomer unit Y2 that is at least one selected from the group consisting of monomer units represented by the following formula (2) and monomer units represented by the following formula (3),

a content of the olefin copolymer having ester group in the resin component is at least 50 mass % with respect to the total mass of the resin component, and

a content of the monomer unit Y2 is at least 3 mass % and not more than 35 mass % with respect to the total mass of the olefin copolymer having ester group

2. The toner according to claim 1, wherein the value of (l+m+n)/W for the olefin copolymer having ester group in the resin component is at least 0.80, where W is the total mass of the olefin copolymer having ester group, l is the mass of monomer units represented by formula (1), m is the mass of monomer units represented by formula (2), and n is the mass of monomer units represented by formula (3).

3. The toner according to claim 1, wherein a content of the crosslinked body from the aliphatic hydrocarbon resin having unsaturated bond is at least′

1.0 mass % and not more than 8.0 mass % with respect to the total mass of the resin component.

4. The toner according to claim 1, wherein the aliphatic hydrocarbon resin having unsaturated bond is polybutadiene.

5. The toner according to claim 4, wherein a weight-average molecular weight of the polybutadiene is at least 10,000 and not more than 300,000.

6. The toner according to claim 4, wherein

the polybutadiene has a 1,2-polybutadiene structure,

a content of the 1,2polybutadiene structure in the polybutadiene is at least 70 mass %, and

at least 50 mass % of the 1,2-polybutadiene structure is a syndiotactic structure.

7. The toner according to claim 4, wherein a melting point of the polybutadiene is at least 60°

C. and not more than 80°

C.

8. The toner according to claim 1, wherein the resin component further contains at least one of an ethylene-methacrylic acid copolymer and an ethylene-acrylic acid copolymer.

9. The toner according to claim 1, wherein

the olefin copolymer having ester group contains an olefin copolymer A having ester group having a softening point of at least 120°

C. and not more than 160°

C., and an olefin copolymer B having ester group having a softening point of at least 70°

C. and not more than 100°

C.

10. The toner according to claim 1, wherein the toner particle contains an aliphatic hydrocarbon having a melting point of at least 50°

C. and not more than 100°

C., and a content of the aliphatic hydrocarbon is at least 1 part by mass and not more than 40 parts by mass with respect to 100 parts by mass of the resin component.

11. The toner according to claim 1, wherein the toner particle contains a silicone oil, and

a content of the silicone oil is at least 1 part by mass and not more than 20 parts by mass with respect to 100 parts by mass of the resin component.

12. The toner according to claim 1, wherein the olefin copolymer having ester group is an ethylene-vinyl acetate copolymer.

13. A method for producing a toner having a toner particle containing a resin component,

the resin component containing an olefin copolymer having ester group and a crosslinked, body from an aliphatic hydrocarbon resin having unsaturated bond,

the method comprising:

a preparation step of preparing a resin fine particle dispersion in which resin fine particles that form the resin component are dispersed in an aqueous medium; and

a crosslinking step of crosslinking, using a crosslinking agent, the aliphatic hydrocarbon resin having unsaturated bond present in the resin fine particles,

wherein

the olefin copolymer having ester group has;

a monomer unit Y1 represented by the following formula (1); and

a monomer unit Y2 that is at least one selected from the group consisting of monomer units represented by the following formula (2) and monomer units represented by the following formula (3),

a content of the olefin copolymer having ester group in the resin component is at least 50 mass % with respect to the total mass of the resin component, and

a content of the monomer unit Y2 is at least 3 mass % and not more than 35 mass % with respect to the total mass of the olefin copolymer having ester group

14. The method for producing the toner according to claim 13, further comprising, after the preparation step of preparing a resin fine particle dispersion:

an aggregation step of aggregating the resin fine particles to form an aggregated particle; and

a fusion step of fusing the aggregated particle by heating,

wherein

the crosslinking step is a step of crosslinking, using the crosslinking agent, the aliphatic hydrocarbon resin having unsaturated bond present in the resin fine particles, the crosslinking step being provided between the preparation step of preparing a resin fine particle dispersion and the aggregation step.

15. The method for producing the toner according to claim 14, wherein

the resin fine particles include a resin fine particle A and a resin fine particle B,

the resin fine particle A contains an olefin copolymer having ester group and does not contain an aliphatic hydrocarbon resin having unsaturated bond,

the resin fine particle B contains an olefin copolymer having ester group and an aliphatic hydrocarbon resin having unsaturated bond, and a median diameter on a volume basis of the resin fine particle B is at least 50 nm and not more than 1,000 nm,

the crosslinking step is a step of crosslinking, using the crosslinking agent, the aliphatic hydrocarbon resin having unsaturated bond present in the resin fine particle B, the crosslinking step being provided after completion of the preparation step of preparing a resin fine particle dispersion and prior to start of the aggregation step, and

the aggregation step is a step of forming an aggregated particle by aggregating the resin fine particle A with the resin fine particle B that has been subjected to the crosslinking step.

16. The method for producing the toner according to claim 14, wherein a content of the aliphatic hydrocarbon resin having unsaturated bond in the resin fine particle B is at least 5 mass % and not more than 20 mass % with respect to the total amount of resin constituting the resin fine particle B.

17. The method for producing the toner according to claim 13, wherein

the olefin copolymer having ester group is an ethylene-vinyl acetate copolymer, and

the aliphatic hydrocarbon resin having unsaturated bond is polybutadiene.