Hoechst Aktiengesellschaft

Jorg Gitzel

Hans-Tobias Macholdt

Erwin Dietz

Wolfgang Knaup

Frank Wehowsky

Detlef Wehle

Gunther Prossel

Hermann Fuchs

Siegfried Schiessler

Alexander Sieber

Rudiger Baur

Siegfried Schiebler

Wilfried Theiss

Tetraphenylborates are obtained in an industrially advantageous grade by spray drying an organic, aqueous or organic-aqueous extract of the tetraphenylborates obtainable in the tetraphenylborates synthesis. It is advantageous to treat the specified extract prior to spray drying with pH-controlling auxiliaries and adsorbents to remove byproducts or to limit their formation. The process gives tetraphenylborates in a homogeneous technical grade, i.e. in a narrow particle size distribution and in a particular particle shape, which improves the dispersibility in the medium to be used.

Process for isolating tetraphenylborates

Polymer ammonium borates having a molecular weight from about 5000 to about 500,000 and obtained by homopolymerization of monomers, such as, for example, diallyldialkylammonium chloride, and by copolymerization of mixtures of two monomers, such as, for example, diallyldimethylammonium chloride and diallylmethyloctylammonium chloride, having molar monomer ratios of about 0.5:0.5 to about 0.95:0.05 in the copolymer, followed, if desired, by anion exchange, and mixtures of these compounds. Polymer ammonium borates according to the invention are suitable as colorless charge-control agents in toners and developers for electrophotographic recording processes and as charge-improving agents in powders and coatings for surface coating.

Polymer ammonium borates and processes for their preparation

Biscationic acid amide and acid imide derivatives as charge controllers

Biscationic acid amide and imide derivatives and processes for their

Use of polymeric ammonium salts which have a molecular weight of about 5000 to about 500,000, and are obtained by homopolymerization of monomers, such as, for example, diallyldialkylammonium chloride, or by copolymerization of mixtures of two monomers, such as, for example, diethyldimethylammonium chloride and diallylmethyloctylammonium chloride, with molar monomer ratios of about 0.5:0.5 to about 0.95:0.05 in the copolymer, and if appropriate subsequent anion exchange, individually or in combination as charge control agents in electrophotographic toners and developers which are employed for copying or duplicating masters and for printing electronically, magnetically or optically stored information or in colorproofing, and as charge control agents in powders and powder coatings.

Polymeric ammonium compounds as charge control agents

Use of colorless highly fluorine-substituted phosphonium compounds as charge control agents for electrophotographic recording processes Use of highly fluorine-substituted phosphonium compounds of the formula (I) ##STR1## in which R.sub.1 to R.sub.4 are hydrogen atoms or organic radicals, at least one of the radicals R.sub.1 to R.sub.4 being a fluorine-substituted, unsaturated and/or saturated alkyl radical having 1 to 30 carbon atoms and 3 to 50 fluorine atoms, which can contain further substituents, or a fluorine-substituted aryl radical or an aralkyl radical which is fluorine-substituted on the aromatic ring, it being possible for the aryl or aralkyl radical to be additionally substituted on the aromatic ring, and in the case of an aralkyl radical the alkyl bridge between the phosphorus atom and the aromatic ring contains 1 to 30 carbon atoms, and not more than three of the radicals R.sub.1 and R.sub.4, independently of one another, are hydrogen atoms, unsaturated or saturated, substituted or unsubstituted alkyl radicals having 1 to 30 carbon atoms, aryl or aralkyl radicals which can be substituted on the aromatic ring, and X.sup.- is an anion, it being possible for the radicals R.sub.1 to R.sub.4 to contain a COO.sup.- or SO.sub.3.sup.- group as substituent and X.sup. - in this case becoming superfluous, individually or in combination as colorless charge control agents having a positive or negative control effect in toners and developers for electrophotographic recording processes.

Use of colorless highly fluorine-substituted phosphonium compounds as

The use of intensely fluorinated ammonium compounds of the general formula (I) ##STR1## in which R.sub.1 to R.sub.4 denote hydrogen atoms or organic radicals, at least one of the radicals R.sub.1 to R.sub.4 denoting a straight-chain or branched fluorine-containing alkyl radical or fluorine-containing alkenyl radical which contains 1 to 69 carbon atoms and 3 to 66 fluorine atoms and which may be substituted, and at most three of the radicals R.sub.1 to R.sub.4 are, independently of one another, hydrogen atoms, straight-chain or branched alkyl radicals or alkenyl radicals containing 1 to 30 carbon atoms, aryl radicals or aralkyl radicals, and X.sup.- denotes an organic or inorganic anion, and of intensely fluorinated iminium compounds of the general formula (II) ##STR2## in which R.sub.9 to R.sub.12 denote hydrogen atoms or organic radicals, at least one of the radicals R.sub.9 to R.sub.12 denoting a straight-chain or branched fluorine-containing alkyl radical or fluorine-containing alkenyl radical which contains 1 to 69 carbon atoms and 3 to 66 fluorine atoms and which may be substituted, and at most three of the radicals R.sub.9 to R.sub.12 denote, independently of one another, hydrogen, straight-chain or branched alkyl radicals or alkenyl radicals containing 1 to 30 carbon atoms, aryl or aralkyl radicals and Y.sup.- is an organic or inorganic anion, as colorless charge control agents having positive or negative control effect in toners and developers for electrophotographic recording processes.

Use of colorless, intensely fluorinated ammonium and iminium compounds

Phosphonium compounds of formula (I): ##STR1## in which at least one of the radicals R.sub.1 to R.sub.4 is a fluorine-substituted, saturated alkyl radical having 1 to 30 carbon atoms and 3 to 50 fluorine atoms, which can contain further substituents, or at least one of the radicals R.sub.1 to R.sub.4 is a fluorine-substituted aryl radical or an aralkyl radical substituted by fluorine on the aromatic ring, it being possible for the aryl or aralkyl radical to be further substituted on the aromatic ring, and the alkyl bridge between the phosphorus atom and the aromatic ring, in the case of an aralkyl radical, containing 1 to 30 carbon atoms, and at most three of the radicals R.sub.1 to R.sub.4 independently of the others are hydrogen atoms, unsaturated or saturated, substituted or unsubstituted C.sub.1 -C.sub.30 alkyl radicals or aryl or aralkyl radicals which can be substituted on the aromatic ring, and R.sub.5 to R.sub.8 are aryl radicals, aralkyl radicals or halogenoaryl radicals, and their preparation by reacting compounds of formula (II): ##STR2## in which R.sub.1 to R.sub.4 are as defined and X.sup.- is a halogen anion, with a borate salt, in water or mixtures of water and an organic solvent, at about 20.degree. C. to about 90.degree. C.

Phosphonium compounds and processes for their preparation

Ammonium compounds of the formula (I) ##STR1## in which at least one of the radicals R.sub.1 to R.sub.4 denotes a fluorine-containing alkyl radical having 4 to 30 carbon atoms and not more than three of the radicals R.sub.1 to R.sub.4 independently of one another denote hydrogen atoms or alkyl or hydroxyalkyl radicals having 1 to 30 carbon atoms, and R.sub.5 to R.sub.8 denote aryl, alkylaryl or halogenoaryl radicals or fluorine atoms, and iminium compounds of the formula (II) ##STR2## in which Q, together with the constituent ##STR3## forms a ring system having 4 to 17 carbon atoms, which can be interrupted by 1 to 4 hetero atoms and contain 2 to 9 double bonds, and which can be substituted by fluorine, chlorine, bromine or iodine atoms or alkyl (C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), nitro or amino groups, R.sub.9 denotes a fluorine-containing alkyl (C.sub.1 -C.sub.30) radical, R.sub.10 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom or an alkyl(C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), nitro or amino group and the radicals R.sub.11 to R.sub.14 denote aryl radicals, alkylaryl radicals, halogenoaryl radicals or fluorine atoms, and mixtures of these compounds and processes for their preparation.

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Hattersheim am Main, Germany

Jorg Gitzel