Abstract: Charge control agent comprising a metal complex salt compound of Formula (I) containing substantially no monoazo compound constituting the ligand thereof, toner containing the charge control agent, and process for manufacturing a metal complex salt compound of Formula (I), which comprises a metallizing reaction for metallizing a monoazo compound of Formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound, in which metallizing reaction a monohydric or dihydric alcohol is used as a reaction-promoting solvent: 1

Abstract: Charge control agent comprising a metal complex salt compound of Formula (I) containing substantially no monoazo compound constituting the ligand thereof, toner containing the charge control agent, and process for manufacturing a metal complex salt compound of Formula (I), which comprises a metallizing reaction for metallizing a monoazo compound of Formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound, in which metallizing reaction a monohydric or dihydric alcohol is used as a reaction-promoting solvent: wherein the substituents are as defined in the disclosure.

Abstract: Charge control agent comprising a metal complex salt compound having a monoazo compound as a ligand, wherein the metal complex salt compound is amorphous, and which is excellent in charge control properties, heat resistance and light fastness, good in dispersibility in, and wettability with, toner resins, hardly damages the photoreceptor when used in a toner, and is unlikely to drop from toner particles during charging; process for manufacturing the charge control agent, comprising subjecting a crystalline metal complex salt compound having a monoazo compound as a ligand to wet milling in an organic solvent, or dissolving the crystalline metal complex salt compound in an organic solvent, and subsequently re-dispersing it in water; and toner for developing electrostatic images comprising said charge control agent, a toner resin, and a coloring agent, and method of use thereof.

Abstract: Monoazo metal compound of formula [I] which is excellent in charge control or charge-enhancing property, and toner for developing electrostatic images and powdery paint for electrostatic painting incorporating thereof:D.sub.3 (Met).sub.2 [I]D is a ligand based on a monoazo compound of formula [II] or [III], Met is a metal atom, and the 3 molecules of D are coordinated to the 2 atoms of Met: ##STR1## R.sup.1 -R.sup.10, and R.sup.21 -R.sup.28 are each H, halogen, nitro, alkyl or haloalkyl, aryl, aralkyl, --SO.sub.2 N(R.sup.11).sub.2 (R.sup.11 is H, alkyl, aryl, aralkyl), --N(R.sup.12).sub.2 (R.sup.12 is H, lower alkyl, aryl, aralkyl, acyl), --CONH(R.sup.13) (R.sup.13 is H, a lower alkyl, aryl, aralkyl); 2 or more of R.sup.1 -R.sup.10 and/or R.sup.21 -R.sup.28 may bind together to form an aromatic or aliphatic ring.

Abstract: Metal compound of formula [I] which is excellent in charge control or charge-enhancing property, and toner for developing electrostatic images and powdery paint for electrostatic painting incorporating thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent a hydrogen, a linear or branched alkyl group, or a linear or branched unsaturated alkyl group; R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, and R.sup.3 and R.sup.4 may bind together to form an aromatic or aliphatic ring which may have one or more substituents of a linear or branched alkyl group, or a linear or branched unsaturated alkyl group; M represents a metal; m represents an integer of 3 or more; n represents an integer of 2 or more.

Abstract: Metal compound of formula [I] which is excellent in charge control or charge-enhancing property, and toner for developing electrostatic images and powdery paint for electrostatic painting incorporating thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent a hydrogen, a linear or branched alkyl group, or a linear or branched unsaturated alkyl group; R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, and R.sup.3 and R.sup.4 may bind together to form an aromatic or aliphatic ring which may have one or more substituents of a linear or branched alkyl group, or a linear or branched unsaturated alkyl group; M represents a metal; m represents an integer of 3 or more; n represents an integer of 2 or more.

Abstract: Monoazo metal compound of formula ?I! which is excellent in charge control or charge-enhancing property, and toner for developing electrostatic images and powdery paint for electrostatic painting incorporating thereof:D.sub.3 (Met).sub.2 ?I!D is a ligand based on a monoazo compound of formula ?II! or ?III!, Met is a metal atom, and the 3 molecules of D are coordinated to the 2 atoms of Met: ##STR1## R.sup.1 -R.sup.10 and R.sup.21 -R.sup.28 are each H, halogen, nitro, alkyl or haloalkyl, aryl, aralkyl, --SO.sub.2 N(R.sup.11).sub.2 (R.sup.11 is H, alkyl, aryl, aralkyl), --N(R.sup.12).sub.2 (R.sup.12 is H, lower alkyl, aryl, aralkyl, acyl), --CONH(R.sup.13) (R.sup.13 is H, a lower alkyl, aryl, aralkyl); 2 or more of R.sup.1 -R.sup.10 and/or R.sup.21 -R.sup.28 may bind together to form an aromatic or aliphatic ring.