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AssigneeHoechst Aktiengesellschaft
InventorsJorg Gitzel, Hans-Tobias Macholdt, Alexander Sieber, Frank Wehowsky, Gunther Prossel
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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.
A method for effecting in toners and developers a positive or negative charge control effect (for electrophotographic recording processes) comprising the step of incorporating the compounds of the formula (I) ##STR8## 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 radial or fluorine-containing alkenyl radical which contains 1 to 69 carbon atoms and 3 to 66 fluorine atoms and which may contain hydroxyl and/or chloromethyl and/or carboxylic acid amide and/or sulfonic acid amide and/or urethane and/or amino and/or R.sub.5 --O--R.sub.6 and/or R.sub.7 --C(O)--O--R.sub.8 groups in which R.sub.5, R.sub.6, R.sub.7 and R.sub.8 and (C.sub.1 -C.sub.30) alkyl radicals 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 alyl radicals or alkenyl radicals containing 1 to 30 carbon atoms, aryl radicals or aralkyl radicals which may be substituted by (D.sub.1 -C.sub.30) alkyl, (C.sub.1 -C.sub.30) alkoxy or hydroxyl groups or halogen atoms, it being possible for two of the radicals R.sub.1 to R.sub.4 to join together to form a mono- or polynuclear ring system containing 4 to 12 carbon atoms which may be interrupted by 1 to 4 hetro atoms and may contain 0 to 6 double bonds and also be substituted by fluorine, chlorine, bromine or iodine atoms, (C.sub.1-C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy, nitro or amino groups, and X.sup.- denotes an organic or inorganic anion, it being possible for the radicals R.sub.1 to R.sub.4 to be substituted by a COO.sup.- or SO.sub.3.sup.- group and X.sup.- ceasing in this case to be applicable, and of intensely fluorinated iminium compounds of the formula (II) ##STR9## 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 contain hydroxyl and/or chloromethyl and/or carboxylic acid amide and/or sulfonic acid amide and/or urethane and/or amino and/or R.sub.5--O--R.sub.6 and/or R.sub.7 C(O)--O--R.sub.8 groups, in which R.sub.5,R.sub.6, R.sub.7 and R.sub.8 have the abovementioned meanings, and at most three of the radicals R.sub.9 to R.sup.12 denote, independently of one another, hydrogen atoms, straight-chain or branched alkyl radicals or alkenyl radicals containing 1 to 30 carbon atoms, it being possible for the aryl radials or aralkyl radicals to be substituted on the aromatic nucleus by (C.sub.1 -C.sub.30) alkyl, (C.sub.1 -C.sub.30) alkoxy, hydroxyl groups or halogen atoms, and for two of the radicals R.sub.9 to R.sup.12 to join together to form a mono- or polynuclear ring system containing 4 to 17 carbon atoms which may be interrupted by 1 to 4 heteroatoms and may contain 2 to 9 double bonds and also be substituted by fluorine, chlorine, bromine or iodine atoms, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) akloxy, nitro or amino groups, and Y.sup.- is an organic or inorganic anion, it being possible for the radicals R.sub.9 to R.sub.12 to be substituted by a COO.sup.- or SO.sub.3.sup.- group and Y.sup.- in this case ceasing to be applicable, as colorless charge control agents having positive or negative charge control effect in toners and developers for electrophotographic recording processes.
A method for effecting in toners and developers a positive or negative charge control effect comprising the step of incorporating the compounds of the formula (I) ##STR11## 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 radicals or fluorine-containing alkenyl radicals which contains 1 to 69 carbon atoms and 3 to 66 fluorine atoms and which may contain hydroxyl and/or chloromethyl and/or carboxylic acid amide and/or sulfonic acid amide and/or urethane and/or amino and/or R.sub.5 --O--R.sub.6 and/or R.sub.7 --C(O)--O--R.sub.8 groups in which R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are (C.sub.1 -C.sub.30) alkyl radicals 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 which may be substituted by (C.sub.1 -C.sub.30) alkyl, (C.sub.1 -C.sub.30) alkoxy or hydroxyl groups or halogen atoms, it being possible for two of the radicals R.sub.1 to R.sub.4 to join together to form a mono- or polynuclear ring system containing 4 to 12 carbon atoms which may be interrupted by 1 to 4 hetero atoms and may contain 0 to 6 double bonds and also be substituted by fluorine, chlorine, bromine or iodine atoms, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy, nitro or amino groups, and X.sup.- denotes an organic or inorganic anion, it being possible for the radicals R.sub.1 to R.sub.4 to be substituted by a COO.sup.- or SO.sub.3.sup.- group and X.sup.- ceasing in this case to be applicable, or an intensely fluorinate iminium compound of the formula ##STR12## 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 radial which contains 1 to 69 carbon atoms and 3 to 66 fluorine atoms and which may contain hyroxyl and/or chloromethyl and/or carboxylic acid amide and/or sulfonic acid amide and/or urethane and/or amino and/or R.sub.5 --O--R.sub.6 and/or R.sub.7 C(O)--O--R.sub.8 groups, in which R.sub.5, R.sub.6, R.sub.7, and R.sub.8 have the abovementioned meanings, and at most three of the radicals R.sub.9 to R.sub.12 denote, independently of one another, hydrogen atoms, straight-chain or branched alkyl radicals or alkenyl radicals containing 1 to 30 carbon atoms, it being possible for the aryl radicals or aralkyl radicals to be substituted on the aromatic nucleus by (C.sub.1 -C.sub.30) alkyl, (C.sub.1 -C.sub.30) alkoxy, hydroxyl groups or halogen atoms, and for two of the radicals R.sub. 9 to R.sub.12 to join together to from a monoor polynuclear ring system containing 4 to 17 carbon atoms which may be interrupted by 1 to 4 heteroatoms and may contain 2 to 9 double bonds and also be substituted by fluorine, chlorine, bromine or iodine atoms, (C.sub.1-C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy, nitro or amino groups, and Y.sup.- is an organic or inorganic anion, it being possible for the radicals R.sub.9 to R.sub.12 to be substituted by COO.sup.- or SO.sub.3.sup.- group and Y.sup.- in this case ceasing to be applicable, or a combination of a said compound of formula (I) and a said compound of formula II, as colorless charge control agents having positive or negative charge control effect in toners and developers for electrophotographic recording processes.
Dependencies are inferred from the claim text.