Use of metal carboxylates and sulfonates as charge control agents

A method of controlling and improving the charge in electrophotographic toners and developers, in powder coating materials, in electret materials and in electrostatic separation processes, comprising adding thereto a metal carboxylate or metal sulfonate of the formula (1), (2) or (2a),

• in which
• A10 is an acid radical of acid A1 as defined below;
• A20 is an acid radical of acid A2 as defined below;
• A30 is as defined for A10 or A20;
• M2 is a divalent metal cation, and
• M3 is a trivalent metal cation,
• wherein
• A1 is
• a) an acid of fornulae (I) to (VIII)
• in which
• R1 is a linear or branched alkyl radical with 1 to 18 carbon atoms,
• R2 and R3 are identical or different and are hydrogen, C1-C8-alkyl, (C1-C18)-hydroxyalkylene, nitro, cyano, fluoro, chloro, bromo, C1-C4-acyl, C6-C10-aryl, heteroaryl, it being possible for aryl and heteroaryl to be substituted by from 1 to 3 of the radicals carboxyl, hydroxyl, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-acyl, halogen, hydroxy-(C1-C4)-alkyl and amino,
• in which
• R4, R5 and R6 are identical or different and are hydrogen, C1-C8-alkyl, (C1-C18)-hydroxyalkylene, nitro, cyano, fluoro, chloro, bromo, C1-C4-acyl, C6-C10-aryl, heteroaryl, it being possible for aryl and heteroaryl to be substituted from 1 to 3 of the radicals carboxyl, hydroxyl, C1-C4-alkoxy, C1-C4-alkyl, halogen, hydroxy-(C1-C4)-alkyl and amino,
• m is 1, 2 or 3, and
• n is O, 1 or 2;
• b) a heteroaromatic mono- or dicarboxylic acid;
• c) a polyanion-forning compound selected from the group consisting of poly(styrenesulfonic acid), poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(anetholesulfonic acid), poly(itaconic acid), poly(vinyl sulfate), poly(vinylsulfonic acid), poly(acrylic acid-co-maleic acid), poly(styrenesulfonic acid-co-maleic acid), poly(ethylene-co-acrylic acid), hectorite, bentonite, algic acid, pectic acid, kappa-, lambda-, and iota-carrageenans, xanthan, gum arabic, dextran sulfate, carboxymethyldextran, carboxymethylcellulose, cellulose sulfate, starch sulfate, lignosulfonates, gum karaya;
• polygalacturonic acid, polyglucuronic acid, polyguluronic acid, polymannuronic acid and copolymers thereof, chondroitin sulfate, heparin, heparan sulfate, hyaluronic acid, dermatan sulfate, keratan sulfate;
• and derivatives of starch, amylose, amylopectin, cellulose, guaran, gum arabic, gum karaya, guar gum, pullulan, xanthan, dextan, curdlan, gellan, carubin, agarose, chitin, and chitosan having the following functional groups:
• carboxymethyl, carboxyethyl, carboxypropyl, 2-carboxyvinyl, 2-hydroxy-3-carboxypropyl, 1,3dicarboxyisopropyl, sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, 5-sulfopentyl, 2-hydroxy-3-sulfopropyl, 2,2-disulfoethyl, 2-carboxy-2-sulfoethyl, maleate, succinate, phthalate, glutarate, aromatic and aliphatic dicarboxylates, xanthogenate, sulfate, phosphate, 2,3-dicarboxy, N,N-di(phosphatomethyl)aminoethyl, N-alkyl-N-phosphatomethyl-aminoethyl, it also being possible for these to contain methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl and 2-hydroxybutyl groups and also esters with aliphatic carboxylic acids (C2 to C18);
• and of the formula (X)
• where n=5 to 5×105;
• and R1, X, A and Y are each identical or different and defined as follows:
• R1=H or CH3;
• X=O or NH;
• A=branched or linear (C1-C18)alkylenes or arylenes;
• Y=SO3, COO, NρR32—A—COO, NρR2—A—SO3σ, N(2 R32—A—PO(OH)Oσ where R3=C1-C8)-alkyl;
• and also copolymers consisting of monomers of the abovementioned compounds and one or more of the following monomers:
• acrylic acid, methacrylic acid, acrylic acid alkyl-(C1-C18)-ester, methacrylic acid alkyl(C1-C18) ester, glycidyl methacrylate, acrylamide, acrylonitrile, methacrylonitrile, ethylene, styrene, α-methylstyrene, styrenesulfonic acid, butadiene, butene, isoprene, vinyl chloride, propylene, maleic anhydride, maleic acid, maleic acid monoalkyl(C1-C18) or dialkyl-(C1-C18) ester, alkyl-( C1-C18) vinyl ether, vinyl alcohol, vinyl acetate, vinylbutyral, vinylimidazole, N-vinyl-2-caprolactam, N-vinylpyrrolidone, mono- or dialkylated (C1-C30) N-vinylpyrrolidone, vinylsulfonic acid, diallydimethylammonium chloride, vinylidene chloride, poly(ethylene glycol) methacrylate, poly(ethylene glycol) acrylate;
• d) a carboxyl- and/or sulfo-containing polyester,
• A2 is an acid of formulae (I) to (VIII);
• an acid of formula (IX)
• in which R4 and R5 are as defined above;
• or a heteroaromatic mono- or dicarboxylic acid;
• or by reacting an acid A1 as defined in c) or d) with an acid A2in the definition of the formulae (I) to (IX) in which R1 to R6 have the definitions specified above and in addition the definition (C1-C18)-alkoxy, hydroxyl, amino, (C1-C18)alkylamino, di(C1-C18)alkylamino, (C1-C18)alkylene-NR7R8, in which R7 and R3 are hydrogen or C1-C8-alkyl;
• and the cation of the metal is divalent or trivalent.