Electric charge controlling agent, toner for developing electrostatic charge image containing the same, and method for forming image using the toner

A method for manufacturing a charge control agent of aggregate particles including an azo-type iron complex salt comprising:

• a diazotization coupling reaction step for preparing monoazo compound represented by the following chemical formula [V]
• wherein in the chemical formula [V], R1—, R2—, R3— and R4— are same or different to each other, and each one thereof is selected from the group 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, mesyl group, a hydroxyl group, an alkoxyl group having 1 to 18 carbon atoms, an acetylamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group having no substitutional groups or one or more substitutional groups selected from the group consisting of hydroxyl group, alkyl group, aryl group, and halogen atom;
• R5— 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 having 1 to 18 carbon atoms;R6— 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 having 1 to 18 carbon atoms;
• an iron-complexing step with said monoazo compound for preparing a counter ion to obtain the azo-type iron complex salt represented by the following chemical formula [I]
• wherein the chemical formula [I], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [V];
• x is mole ratio and is 0.6 to 0.9;
• or the following chemical formula [II]
• wherein the chemical formula [II], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [V];
• y is mole ratio and 0<y≦0.2;
• a step for filtrating, washing and drying the azo-type iron complex salt, said iron-complexing step with the monoazo compound is carried out in a mixed solvent of water and 0.1 to 30% by weight of a lower alcohol having 1to 6 carbon atoms.

A charge control agent of aggregate particles including an azo-type iron complex salt manufactured by a method comprising:

• a diazotization coupling reaction step for preparing monoazo compound represented by the following chemical formula [V]
• wherein in the chemical formula [V], R1—, R2—, R3— and R4— are same or different to each other, and each one thereof is selected from the group 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, a mesyl group, a hydroxyl group, an alkoxyl group having 1 to 18 carbon atoms, an acetylamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group having no substitutional groups or one or more substitutional groups selected from the group consisting of hydroxyl group, alkyl group, aryl group, and halogen atom;
• R5— is a hydrogen atom, an alkyl group having a straight or branch chain of 1 to 18 carbon atoms, a hydrogen group or an alkoxyl group having 1 to 18 carbon atoms;
• R6— 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 having 1 to 18 carbon atoms;
• an iron-complexing step with said monoazo compound for preparing a counter ion to obtain the azo-type iron complex salt represented by the following chemical formula [I]
• wherein the chemical formula [I], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [V ];
• x is mole ratio and 0.6 to 0.9;
• or the following chemical formula [II]
• wherein the chemical formula [II], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [V ];
• y is mole ratio and 0<y≦0.2;
• a step for filtrating, washing and drying the azo-type iron complex salt, said iron-complexing step with said monoazo compound is carried out in mixed solvent of water and 0.1 to 30% by weight of a lower alcohol having 1 to 6 carbon atoms, and said aggregate particles have 0.5 to 5.0 microns of an average particle size.

A toner for developing an electrostatic image comprising:

• a resin for the toner:
• and
• a charge control agent of aggregate particles including an azo-type iron complex salt represented by the following chemical formula [I]
• wherein in the chemical formula [I], R1—, R2—, R3— and R4— are same or different to each other, and each one thereof is selected from the group 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, a mesyl group, a hydroxyl group, an alkoxyl group having 1 to 18 carbon atoms, an acetylamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group having no substitutional groups or one or more substitutional groups selected from the group consisting of hydroxyl group, alkyl group, aryl group, and halogen atom;
• R5— 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 having 1 to 18 carbon atoms;
• R6— 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 having 1 to 18 carbon atoms;
• x is mole ratio and 0.6 to 0.9;
• or the following chemical formula [II]
• wherein in the chemical formula [II], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [V];
• y is mole ratio and 0<y≦0.2;
• and said aggregate particles have 0.5 to 5.0 microns of an average particle size.

An image formation process of electrophotography comprising:

• developing an electrostatic latent image on an electrostatic latent image frame by a developer including a toner, said toner comprises a resin for the toner and a charge control agent of aggregate particles comprising an azo-type iron complex salt represented by the following chemical formula [I]
• wherein the chemical formula [I], R1—, R2—, R3— and R4— are same or different to each other, and each one thereof is selected from the group 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, a mesyl group, a hydroxyl group, an alkoxyl group having 1 to 18 carbon atoms, an acetylamino group, a benzoylamino group, a halogen atom, a nitro group and an aryl group having no substitutional groups or one or more substitutional groups selected from the group consisting of hydroxyl group, alkyl group, aryl group, and halogen atom;
• R5— 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 having 1 to 18 carbon atoms;
• R6— 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 having 1 to 18 carbon atoms;
• x is mole ratio and 0.6 to 0.9;
• or the following chemical formula [II]
• wherein in the chemical formula [II], R1—, R2—, R3—, R4—, R5— and R6— are the same as in chemical formula [I];
• y is mole ratio and 0<y≦0.2;
• and said aggregate particles have 0.5 to 5.0 microns of an average particle size.