Diallylammonium compounds, processes for their preparation and their use
AssigneeHoechst Aktiengesellschaft
InventorsRudiger Baur, Hans-Tobias Macholdt
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Abstract
Ionic monomeric diallylammonium compounds having a targeted combination of diallylammonium cations with selected anions have particularly high and constant charge control properties and very good heat stabilities and dispersibilities. The compounds according to the invention are outstandingly suitable for use as colorless charge control agents in toners and developers for electrophotographic recording processes and for use as charge-improving agents in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.
Claims17
An ionic monomeric diallylammonium compound of the formula (I) ##STR6## or mixture thereof, in which the radicals R.sub.1 to R.sub.12 independently of one another are each a hydrogen atom, a halogen atom, a hydroxyl radical, a primary, secondary or tertiary amino radical, a carboxylic acid or carboxylic acid ester radical, an acyl radical, a sulfonic acid or sulfonic acid ester radical, a cyano radical or a nitro radical, or are in each case a radical based on an aliphatic or aromatic hydrocarbon, a polyoxyalkylene radical of the formula (alkylene (C.sub.1 -C.sub.5)--O.sub.)n --R, in which R is a hydrogen atom, an alkyl(C.sub.1 -C.sub.4) radical or an acyl radical and n is a number from 1 to 10, a pyridyl radical, alkoxy radical, aralkoxy radical, or a combination thereof, and wherein R.sub.1 and R.sub.2 may together form a pyridinium, morpholinium or quinolinium ring system;
- and A.sup.- is in each case the stoichiometric equivalent of an inorganic anion with the proviso that in the case of a compound A.sup.- is not Cl.sup.-, Br.sup.-, thiocyanate, NO.sub.3.sup.- or SO.sub.4.sup.2-, and in the case of a mixture in at least one compound in the mixture A.sup.- is not Cl.sup.-, Br.sup.-, or SO.sub.4.sup.2-, and with the further proviso that di(2-propenyl)-ammoniumtetrafluoroborate, di(2-propenyl)ammoniumfluoride and di(2-propenyl)ammoniumtosylate are excluded;
- or is the stoichiometric equivalent of a molybdatophosphate, tungstophosphate or a silicomolybdate or of a borate of the formula (II) ##STR7## in which the radicals R.sub.13 to R.sub.16 on the borate anion independently of one another are aliphatic or cycloaliphatic radicals, or aryl or pyridyl or arylalkyl radicals, fluorophenyl, chlorophenyl, tolyl, methoxyphenyl, biphenyl, benzyl, or are fluorine atoms;
- or of an organic anion,
- wherein the organic anion is based on a phenolate, olefinic, aliphatic or aromatic carboxylate, sulfonate, thiolate or sulfate, in which the alkyl, alkenyl or aryl radicals optionally are perfluorinated, or based on a disulfo-pyrrolidinium-betaine of the formula (III) ##STR8## in which R.sub.1 and R.sub.2 have the above meaning and X and Y are in each case a straight-chain or branched aliphatic, saturated or unsaturated alkyl(C.sub.1 -C.sub.18) radical or alkoxy(C.sub.1 -C.sub.18) radical,
- or A.sup.- is a combination of these anions;
- or a mixture of such compounds.
Dependencies are inferred from the claim text.