Hoechst Aktiengesellschaft

Cassella Aktiengesellschaft

Frank Wehowsky

Rolf Kleber

Wolfgang Knaup

Lothar Jaeckel

Hans-Tobias Macholdt

Karl Hintermeier

Jorg Gitzel

Gunter Prossel

Manfred Muller

Heinrich Bathelt

Gunther Prossel

Alexander Sieber

Werner Lotz

Winfried Ehrl

Manfred Seidel

Hans Wagener

Norbert Schmitt

Jan-Hilbert Mast

Hubert Herdt

Lothar Jackel

Wolfgang Glenz

Klaus Kaschub

Martin Liebiger

New saturated fluoroalkylamines and carboxyalkylbetaines and alkylsulfobetaines derived therefrom, and mixtures containing the new fluoroalkylamines and mixtures containing the new fluorobetaines are described. The saturated fluoroalkylamines conform to the formula below ##STR1## in which n is an integer from 3 to 17 and R.sup.1 and R.sup.2 are C.sub.1 to C.sub.4 -alkyl, C.sub.1 to C.sub.4 -hydroxyalkyl or hydrogen, with the proviso that only one of the two substituents R.sup.1 and R.sup.2 is hydrogen. The carboxyalkylbetaines and sulfobetaines and the mixtures thereof are highly effective products for reducing the surface tension of water/air systems and the interfacial tension of water/hydrocarbon systems.

Saturated fluoroalkylamines and their derivatives, and mixtures thereof

The new compounds have the formula below ##STR1## in which R.sub.f is a perfluoroalkyl radical having 4 to 20 carbon atoms,

Surface-active compounds having a perfluoroalkyl group and a

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

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.

Ammonium and iminium compounds

Urethanes made from aliphatic fluorinated alochols, isocyanates and substituted aromatic compounds, a process for their preparation, and their use. The novel urethanes are synthesized from an aliphatic fluorinated alcohol, an isocyanate and a specific substituted phenol or aniline compound. They are prepared by reacting an aliphatic fluorinated alcohol with a di- or triisocyanate to form a fluorinated alcohol/isocyanate adduct and reacting this adduct with a certain substituted phenol or aniline to form the urethanes intended. The novel urethanes are preferably used for oleophobic and hydrophobic finishing of textiles and leather.

Urethane made from aliphatic fluorinated alcohols, isocyanates and

The novel urethanes are composed essentially of fluoroalcohol-isocyanate adducts as the fluoro component and a polysiloxane component, the two components being combined in a structurally specific manner. The novel urethanes are prepared by reacting the fluoroalcohol-isocyanate adducts with the polysiloxane in a molar ratio of 1 to 2:1 at a temperature of 30.degree. to 130.degree. C. The novel urethanes are preferably used for finishing textiles, to which they also impart the property of a soft handle in addition to good hydrophobicity and oleophobicity. They are also suitable for finishing leather, skins and wood.

Urethanes containing fluorine and polysiloxane, process for their

The molecule of the new urethanes contains an aliphatic fluoroalcohol, an isocyanate and an aromatic dihydroxy, diamino, aminohydroxy, aminocarboxy or hydroxycarboxy compound. They are prepared by reacting an aliphatic fluoroalcohol with a diisocyanate or triisocyanate to give the fluoroalcohol/isocyanate adduct and by reacting this adduct with said aromatic compound to give the desired urethanes composed of an aliphatic fluoroalcohol, an isocyanate and the bifunctional aromatic compound mentioned, and also be reacting a urethane of this type which also carries an active hydrogen atom on the bifunctional aromatic compound, with an isocyanate compound containing one or more isocyanate groups. The new urethanes are preferably used for imparting an oleophobic and hydrophobic finish to textiles and leather.

Urethanes composed of aliphatic fluoroalcohols, isocyanates and aromatic

An agent effective for oleophobizing and hydrophobizing textiles is an aqueous anionic dispersion which comprises water and

Aqueous anionic dispersion

The novel urethanes, in addition to at least one perfluoroalkyl group, also contain epichlorohydrin groups and dialcohol radicals in the molecule. They are prepared by reacting a fluorine-containing alcohol with epichlorohydrin to give the perfluoroalkyl-epichlorohydrin adduct, reacting this adduct with a di- or triisocyanate to give the perfluoroalkyl-epichlorohydrin-isocyanate adduct and by reacting this adduct with a dialcohol or a monoetherified dialcohol to give the desired urethanes having a perfluoroalkyl group and having epichlorohydrin groups and dialcohol radicals, and by reacting a suitable urethane compound of this type with a perfluoroalkyl-containing di- or triisocyanate to give the desired urethanes having a plurality of perfluoroalkyl groups and having epichlorohydrin groups and dialcoholradicals. The novel urethanes are preferably used for the oleophobic and hydrophobic finishing of textiles.

Urethanes which contain perfluoroalkyl groups, epichlorohydrin groups

The novel urethanes correspond to the formula I below ##STR1## in which a denotes a number from 5 to 17 and b denotes a number from 1 to 7. These urethanes are prepared by reacting the corresponding perfluoroalkylethanol/epichlorohydrin adducts with toluelene diisocyanates. The novel aqueous dispersions are essentially composed of the novel urethanes, cationic or betaine emulsifiers and non-ionic emulsifiers, water-insoluble carboxylic and/or dicarboxylic acid esters and alkanediols or polyalkanediols which can be etherified on one or both sides, in water. The novel urethanes and the novel aqueous dispersions are used to impart an oleophobic and hydrophobic finish to textiles, leather and furs. They are also suitable for the treatment of unpainted timber, for example unpainted furniture.

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Burgkirchen, Germany

Frank Wehowsky