Binder resin for electrostatic image developing toner, binder resin liquid dispersion for electrostatic image developing toner, electrostatic image developing toner and production processes thereof

Abstract

A binder resin for an electrostatic image developing toner is obtained by a polycondensation reaction of a polycarboxylic acid and a polyol, wherein the polycarboxylic acid includes a compound represented by at least one of formula (1) and formula (2) as defined in the specification in an amount of from about 50 to about 100 mol %; the polyol includes a compound represented by formula (3) as defined in the specification in an amount of from about 10 to about 100 mol %; and a content of a catalyst-originated metal element in the binder resin is about 100 ppm or less.

Description

Claims

1. A binder resin for an electrostatic image developing toner, obtained by a polycondensation reaction of a polycarboxylic acid and a polyol, wherein the polycarboxylic acid comprises a compound represented by at least one of formula (1) and formula (2) in an amount of from about 50 to about 100 mol %;the polyol comprises a compound represented by formula (3) in an amount of from about 10 to about 100 mol %; anda content of a catalyst-originated metal element in the binder resin is about 100 ppm or less: R1OOCA1mB1nA1lCOOR1′  (1)wherein A1 represents a methylene group;B1 represents an aromatic hydrocarbon group;R1 and R1′ each independently represents a hydrogen atom or a monovalent hydrocarbon group;m and l each independently represents an integer satisfying 1≦m+l≦12; andn represents an integer satisfying 1≦n≦3; R2OOCA2pB2qA2rCOOR2′  (2)wherein A2 represents a methylene group;B2 represents an alicyclic hydrocarbon group;R2 and R2′ each independently represents a hydrogen atom or a monovalent hydrocarbon group; andp, q and r each independently represents an integer satisfying 0≦p≦6, 0≦r≦6 and 1≦q≦3, respectively; HOXh—Ph—Y—Ph—XkOH   (3)wherein X represents an alkylene oxide group;Y represents SO2 or C6H10; andh and k each independently represents an integer satisfying 1≦h≦3 and 1≦k≦3, respectively.

2. The binder resin for an electrostatic image developing toner according to claim 1, wherein in formula (1), m and 1 are the same number.

3. The binder resin for an electrostatic image developing toner according to claim 1, wherein in formula (3), h and k are the same number.

4. The binder resin for an electrostatic image developing toner according to claim 3, wherein the compound represented by formula (3) is at least one of a bisphenol S derivative and a bisphenol Z derivative.

5. The binder resin for an electrostatic image developing toner according to claim 1, wherein the polycondensation reaction of a polycarboxylic acid and a polyol is performed with a sulfur acid.

6. The binder resin for an electrostatic image developing toner according to claim 5, wherein the sulfur acid is an organic sulfur acid having a surface activating effect.

7. The binder resin for an electrostatic image developing toner according to claim 6, wherein the organic sulfur acid having a surface activating effect is a dodecylbenzenesulfonic acid.

8. A process for producing a binder resin for an electrostatic image developing toner, the process comprising: polycondensing a polycarboxylic acid and a polyol,wherein the polycarboxylic acid comprises a compound represented by at least one of formula (1) and formula (2) in an amount of from about 50 to about 100 mol %;the polyol comprises a compound represented by formula (3) in an amount of from about 10 to about 100 mol %; anda content of a catalyst-originated metal element in the binder resin is about 100 ppm or less: R1OOCA1mB1nA1lCOOR1′  (1)wherein A1 represents a methylene group;B1 represents an aromatic hydrocarbon group;R1 and R1′ each independently represents a hydrogen atom or a monovalent hydrocarbon group;m and l each independently represents an integer satisfying 1≦m+l≦12; andn represents an integer satisfying 1≦n≦3; R2OOCA2pB2qA2rCOOR2′  (2)wherein A2 represents a methylene group;B2 represents an alicyclic hydrocarbon group;R2 and R2′ each independently represents a hydrogen atom or a monovalent hydrocarbon group; andp, q and r each independently represents an integer satisfying 0≦p≦6, 0≦r≦6 and 1≦q≦3, respectively; HOXh—Ph—Y—Ph—XkOH   (3)wherein X represents an alkylene oxide group;Y represents SO2 or C6H10; andh and k each independently represents an integer satisfying 1≦h≦3 and 1≦k≦3, respectively.

9. The process for producing a binder resin for an electrostatic image developing toner according to claim 8, wherein the polycondensation reaction of a polycarboxylic acid and a polyol is performed with a sulfur acid.

10. The process for producing a binder resin for an electrostatic image developing toner according to claim 9, wherein the sulfur acid is an organic sulfur acid having a surface activating effect.

11. The process for producing a binder resin for an electrostatic image developing toner according to claim 10, wherein the organic sulfur acid having a surface activating effect is a dodecylbenzenesulfonic acid.

12. The process for producing a binder resin for an electrostatic image developing toner according to claim 8, which further comprises: rapidly cooling a resin after polymerization at about 1 to about 50° C./min.

13. A binder resin liquid dispersion for an electrostatic image developing toner, comprising: a binder resin for an electrostatic image developing toner dispersed in the binder resin liquid dispersion, wherein the binder resin is obtained by a polycondensation reaction of a polycarboxylic acid and a polyol,wherein the polycarboxylic acid comprises a compound represented by at least one of formula (1) and formula (2) in an amount of from about 50 to about 100 mol %;the polyol comprises a compound represented by formula (3) in an amount of from about 10 to about 100 mol %; anda content of a catalyst-originated metal element in the binder resin is about 100 ppm or less: R1OOCA1mB1nA1lCOOR1′  (1)wherein A1 represents a methylene group;B1 represents an aromatic hydrocarbon group;R1 and R1′ each independently represents a hydrogen atom or a monovalent hydrocarbon group;m and l each independently represents an integer satisfying 1≦m+l≦12; andn represents an integer satisfying 1≦n≦3; R2OOCA2pB2qA2rCOOR2′  (2)wherein A2 represents a methylene group;B2 represents an alicyclic hydrocarbon group;R2 and R2′ each independently represents a hydrogen atom or a monovalent hydrocarbon group; andp, q and r each independently represents an integer satisfying 0≦p≦6, 0≦r≦6 and 1≦q≦3, respectively; HOXh—Ph—Y—Ph—XkOH   (3)wherein X represents an alkylene oxide group;Y represents SO2 or C6H10; andh and k each independently represents an integer satisfying 1≦h≦3 and 1≦k≦3, respectively.

14. A process for producing an electrostatic image developing toner, comprising: aggregating a binder resin in a liquid dispersion comprising at least a binder resin liquid dispersion to obtain aggregate particles; andheating and coalescing the aggregate particles,wherein the binder resin liquid dispersion is a binder resin liquid dispersion for an electrostatic image developing toner according to claim 13.

15. An electrostatic image developing toner produced by a process according to claim 14.

16. An electrostatic image developing toner produced by kneading and pulverizing a mixture comprising a binder resin for an electrostatic image developing toner according to claim 1.

17. An electrostatic image developer comprising an electrostatic image developing toner according to claim 16 and a carrier.

18. An image forming method comprising: forming an electrostatic latent image on a surface of a latent image-holding member;developing the electrostatic latent image formed on the surface of the latent image-holding member with a toner form a toner image;transferring the toner image formed on the surface of the latent image-holding member to a surface of a transferee member; andheat-fixing the toner image transferred to the surface of the transferee member,wherein the toner is an electrostatic image developing toner according to claim 16.

19. An image forming method comprising: forming an electrostatic latent image on a surface of a latent image-holding member;developing the electrostatic latent image formed on the surface of the latent image-holding member with an electrostatic image developer to form a toner image;transferring the toner image formed on the surface of the latent image-holding member to a surface of a transferee member; andheat-fixing the toner image transferred to the surface of the transferee member,wherein the electrostatic image developer is an electrostatic image developer according to claim 17.