Monoazo metal compound, composition thereof, charge control agent, toner and powdery paint

A toner for developing electrostatic images comprising a coloring agent, a resin and a monoazo metal compound represented by the formula ›IV! below as charge control agent

• D.sub.6 (Met).sub.4 ›IV!
• wherein D represents a ligand based on a monoazo compound having 2 metallizable --OH groups represented by formula ›II! or ›III! below, Met represents a metal atom, and the 6 molecules of D are coordinated to the 4 atoms of Met:
• ##STR15## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.11).sub.2 (the two R.sup.11 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.12).sub.2 (the two R.sup.12 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.13) (R.sup.13 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.1 through R.sup.10 may bind together to form an aromatic or aliphatic ring;
• ##STR16## wherein R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27 and R.sup.28 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.29).sub.2 (the two R.sup.29 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.30).sub.2 (the two R.sup.30 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.31) (R.sup.31 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.21 through R.sup.28 may bind together to form an aromatic or aliphatic ring.

A toner for developing electrostatic images comprising a coloring agent, a resin and a composition as charge control agent comprising 2 or 3 monoazo metal compounds selected from the group consisting of monoazo metal compounds represented by formula ›VI! below, monoazo metal compounds represented by formula ›VII! below, and monoazo metal compounds represented by formula ›VIII! below ##STR19## in formulas ›VI!, ›VII! and ›VIII!, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.11).sub.2 (the two R.sup.11 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.12).sub.2 (the two R.sup.12 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.13) (R.sup.13 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);

• 2 or more of R.sup.1 through R.sup.10 may bind together to form an aromatic or aliphatic ring;
• Met represents a metal atom;
• and in formula ›VIII!, A.sup.+ represents a cation.

A toner for developing electrostatic images comprising a coloring agent, a resin and a composition as charge control agent comprising 2 or 3 monoazo metal compounds selected from the group consisting of monoazo metal compounds represented by formula ›IX! below, monoazo metal compounds represented by formula ›X! below, and monoazo metal compounds represented by formula ›XI! below ##STR21## In formulas ›IX!, ›X! and ›XI!, R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27 and R.sup.28 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.29 ).sub.2 (the two R.sup.29 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.30).sub.2 (the two R.sup.30 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.31) (R.sup.31 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);

• 2 or more of R.sup.21 through R.sup.28 may bind together to form an aromatic or aliphatic ring;
• Met represents a metal atom;
• and in formula ›XI!, A.sup.+ represents a cation.

A powdery paint for electrostatic painting comprising a resin and a monoazo metal compound as charge enhancer represented by the formula ›I! below

• D.sub.3 (Met).sub.2 ›I!
• wherein D represents a ligand based on a monoazo compound having 2 metallizable --OH groups represented by formula (II! or ›III! below, Met represents a metal atom, and the 3 molecules of D are coordinated to the 2 atoms of Met ##STR22## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.11).sub.2 (the two R.sup.11 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.12).sub.2 (the two R.sup.12 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.13) (R.sup.13 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.1 through R.sup.10 may bind together to form an aromatic or aliphatic ring ##STR23## wherein R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27 and R.sup.28 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.29 ).sub.2 (the two R.sup.29 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sub.30).sub.2 (the two R.sup.30 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.31) (R.sup.31 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.21 through R.sup.28 may bind together to form an aromatic or aliphatic ring.

A powdery paint for electrostatic painting comprising a resin and a monoazo metal compound as charge enhancer represented by the formula ›IV! below

• D.sub.6 (Met).sub.4 ›IV!
• wherein D represents a ligand based on a monoazo compound having 2 metallizable --OH groups represented by formula ›II! or ›III! below, Met represents a metal atom, and the 6 molecules of D are coordinated to the 4 atoms of Met ##STR24## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.11).sub.2 (the two R.sup.11 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.12).sub.2 (the two R.sup.12 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.13) (R.sup.13 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.1 through R.sup.10 may bind together to form an aromatic or aliphatic ring ##STR25## wherein R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27 and R.sup.28 independently represent a hydrogen, a halogen, a nitro group, an alkyl or haloalkyl group having 1 to 20 carbon atoms, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, --SO.sub.2 N(R.sup.29).sub.2 (the two R.sup.29 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution), --N(R.sup.30).sub.2 (the two R.sup.30 groups, whether identical or not, represent a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, an aralkyl group having or not having nuclear substitution, or an acyl group), or --CONH(R.sup.31) (R.sup.31 represents a hydrogen, a lower alkyl group, an aryl group having or not having nuclear substitution, or an aralkyl group having or not having nuclear substitution);
• 2 or more of R.sup.21 through R.sup.28 may bind together to form an aromatic or aliphatic ring.