Charge control agent and toner for electrostatic image development

Abstract

A charge control agent of the present invention comprises aggregate particles of an azo-type iron complex salt represented by the following chemical formula [I] in the chemical formula [I], R 1 —, R 2 —, R 3 —, R 4 —, R 5 — and R 6 — are same or different to each other, n is 0.7 to 0.99, the aggregate particles have an average particle size of 1 to 4 microns and an average particle size of a primary particulate crystalline, that is fined the aggregate particles with ultrasonic irradiation, is at most 3 microns. A toner for developing an electrostatic image comprises a resin for the toner and the charge control agent.

1 . A charge control agent comprising aggregate particles of an azo-type iron complex salt represented by the following chemical formula [I]:  
     
       
         
         
             
             
         
       
       in the chemical formula [I], R 1− , R 2− , R 3− , and R 4−  are same or different to each other, and one thereof is selected from the groups consisting of a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, an alkenyl group having a straight to branch chain of 2 to 18 carbon atoms, a sulfonamide group being to have substitutional groups, a mesyl group, a hydroxyl group, an alkoxyl group of 1 to 18 carbon atoms, an acytlamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group being to have substitutional groups; R 5−  is a hydrogen atom, an alkyl group having a straight or branch chain fo 1 to 18 carbon atoms, a hydroxyl group or an alkoxyl group of 1 to 18 carbon atoms; R 6−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl, group, a carboxyl group, a halogen atom, or an alkoxyl group of 1 to 18 carbon atoms; n is 0.7 to 0.99,  
       said aggregate particles have an average size of 1 to 4 microns and an average particle size of a primary particulate crystalline that is fined the aggregate particles with ultrasonic irradiation, is at most 3 microns.  
     
   
   
       2 . The charge control agent according to  claim 1 , wherein a primary particle of said azo-type iron complex salt has a size of at most 4 microns.  
   
   
       3 . The charge control agent according to  claim 1 , wherein said azo-type iron complex salt is represented by the following chemical formula [II] 
     
       
         
         
             
             
         
       
       in the chemical formula [II], n is the same above.  
     
   
   
       4 . The charge control agent according to  claim 1 , wherein said aggregate particles of the azo-type iron complex salt are almost uniform platy-shape.  
   
   
       5 . The charge control agent according to  claim 1 , wherein a specific surface area determined from said average particle size of the primary particulate crystalline is at least 10 m 2 /g  
   
   
       6 . The charge control agent according to  claim 1 , wherein allowable residual sulfate ion is at most 100 ppm, and allowable residual chloride ion is at most 200 ppm.  
   
   
       7 . The charge control agent according to  claim 1 , further comprising butanol of an amount of 0.01 to 1.00% by weight.  
   
   
       8 . A method for manufacturing a charge control agent comprising steps of: 
 a diazotization coupling reaction step for preparing monoazo comound represented by the following chemical formula [III]                         (in the chemical formula [III], R 1− , R 2− , R 3− , and R 4−  are same or different to each other, and one thereof is selected from the groups consisting of a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, an alkenyl group having a straight or branch chain of 2 to 18 carbon atoms, a sulfonamide group being to have substitutional, a mesyl group, a hydroxyl group, an alkoxyl group of 1 to 18 carbon atoms, an acytlamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group being to have substitutional groups; R 5−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl group or an alkoxyl group of 1 to 18 carbon atoms; R 6−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom or an alkoxyl group of 1 to 18 carbon atoms):    a step for iron-complexing with said monoazo compound:    a counter ion-exchanging step for preparing an azo-type iron complex salt represented by the following chemical formula [I]                         (in the chemical formula [I], R 1− , R 2− , R 3− , and R 4−  are same or different to each other, and one thereof is selected from the groups consisting of a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, an alkenyl group having a straight to branch chain of 2 to 18 carbon atoms, a sulfonamide group being to have substitutional groups, a mesyl group, a hydroxyl group, an alkoxyl group of 1 to 18 carbon atoms, an acytlamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group being to have substitutional groups; R 5−  is a hydrogen atom, an alkyl group having a straight or branch chain fo 1 to 18 carbon atoms, a hydroxyl group or an alkoxyl group of 1 to 18 carbon atoms; R 6−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl, group, a carboxyl group, a halogen atom, or an alkoxyl group of 1 to 18 carbon atoms; n is 0.7 to 0.99), and    a step for filtrating and drying the azo-type iron complex salt: at least one of said step for the iron-complexing and said counter ion-exchanging step is carried out in mixed solvent of a lower alcohol having 1 to 6 carbon atoms and water included at least 70% by weight thereof,    and said charge control agent comprises aggregate particles of said azo-type iron complex salt that said aggregate particles have an average particle size of 1 to 4 microns and an average particle size of a primary particulate crystalline, that is fined the aggregate particles with ultrasonic irradiation, is at most 3 microns.    
   
   
       9 . The method according to  claim 7 , wherein said mixed solvent includes the lower alcohol of 0.5 to 9.0% by weight.  
   
   
       10 . The method according to  claim 8 , wherein said lower alcohol is butanol.  
   
   
       11 . A charge control agent manufactured from a method comprising steps: 
 a diazotization coupling reaction step for preparing monoazo compound represented by the following chemical formula [III]                         (in the chemical formula [III], R 1− , R 2− , R 3− , and R 4−  are same or different to each other, and one thereof is selected from the groups consisting of a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, an alkenyl group having a straight or branch chain of 2 to 18 carbon atoms, a sulfonamide group being to have substitutional, a mesyl group, a hydroxyl group, an alkoxyl group of 1 to 18 carbon atoms, an acytlamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group being to have substitutional groups; R 5−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl group or an alkoxyl group of 1 to 18 carbon atoms; R 6−  is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom or an alkoxyl group of 1 to 18 carbon atoms):    a step for iron-complexing with said monoazo compound:    a counter ion-exchanging step for preparing an azo-type iron complex salt represented by the following chemical formula [I]                         (in the chemical formula [I], R 1− , R 2− , R 3− , R 4− , R 5−  and R 6−  are the same above, n is 0.7 to 0.99): and    a step for filtrating and drying he azo-type iron complex salt: at least one of said step for the ion-complexing and said counter ion-exchanging step is carried out in mixed solvent of a lower alcohol having 1 to 6 carbon atoms and water included at least 70% by weight thereof,    and said charge control agent comprises aggregate particles of said azo-type iron complex salt that said aggregate particles have an average particle size of 1 to 4 microns and an average particle size of a primary particulate crystalline, that is fined the aggregate particles with ultrasonic irradiation, is at most 3 microns.    
   
   
       12 . The charge control agent to  claim 11 , wherein said mixed solvent includes the lower alcohol of 0.5 to 9.0% by weight.  
   
   
       13 .- 23 . (canceled)