Ciba-geigy Corporation

Ciba-geigy Ag

Horst H Jager

Armin Hiestand

Jacques Bersier

Peter Rohringer

Alois Puntener

Hansrudolf Schwander

Hans Wegmuller

Hans Mollet

Eric Plattner

Christos Comninellis

Suresh C Agarwal

Rudiger Oxenius

Nitya G Podder

Bernard Chambon

The invention relates to a process for the preparation of 1:2 chromium, 1:2 cobalt, 1:2 nickel or 1:2 iron complex azo dyes diazotisation, coupling and metallizing, without isolation of the coupling product, which process comprises diazotizing at least one amine of the benzene or naphthalene series in aqueous solution and coupling the diazonium compound so obtained to at least one coupling component of the benzene or naphthalene series or of the heterocyclic series, such that the azo dye obtained as intermediate contains groups suitable for metal complex formation, and carrying out the diazotization or coupling in the presence of a chromium, cobalt, nickel or iron donor. The dyes obtained by the process of the invention are suitable for dyeing in particular wool or synthetic textile polyamide fibre materials as well as leather, and for use as wood mordant dyes.

Process for the preparation of 1:2 metal complex azo compounds by

The invention relates to dyestuff preparations comprising water, a water-insoluble or sparingly water-soluble dye, a dispersant, a humectant, and optionally further additives, wherein said humectant is a compound of the formula I ##STR1## wherein R is a C.sub.1 -C.sub.16 alkyl group which is unsubstituted or substituted by OH, CN, halogen or --N(C.sub.1 -C.sub.4 alkyl).sub.2, and R' is hydrogen or the --CH.sub.2 --CHOH--CH.sub.2 OH group. These preparations are suitable for use in aqueous or aqueous-organic dye liquors or printing inks or also for obtaining printing pastes. After partial or complete dehydration they are also very readily redispersible.

Liquid dyestuff preparations

An electrochemical process for the preparation of benzanthrones and planar, polycyclic aromatic oxygen-containing compounds is described. The process is carried out in an acid medium in an electrolytic cell which is separated by a diaphragm into a cathode compartment and an anode compartment. In the cathode compartment, anthraquinone or an anthraquinone derivative is reduced electrolytically to oxanthrone and the latter is reacted with glycerol to give the corresponding benzanthrone. In the anode compartment, a transition metal ion is simultaneously converted electrolytically from a lower oxidation stage into the next higher oxidation stage. The metal ion of higher valency is then used in the anolyte as an oxidizing agent by means of which the corresponding oxygen-containing compounds are obtained, starting from planar, polycyclic aromatic compounds.

Electrochemical process for the preparation of benzanthrones and planar,

An electrochemical process for the production of benzanthrone by reaction of anthraquinone as, starting material, with glycerol, which process comprises reducing anthraquinone, which may additionally contain electronegative substituents, at the cathode in an electrolytic cell in acid medium, and simultaneously cyclizing the reduced semiquinone form with glycerol to produce the corresponding benzanthrone. The novel process affords numerous advantages compared with chemical reduction methods.

Electrochemical process for the production of benzanthrone

A method of finishing synthetic organic fibrous material, in particular of providing such material with an antistatic finish and simultaneously improving the dirt repellency is provided, which comprises treating said material with aqueous or organic solutions or emulsions which contain (a) at least one copolymer derived from at least two of the monomers of formulae ##STR1## wherein R is straight-chain or branched alkyl of 1 to 8 carbon atoms, R.sub.1 is hydrogen or methyl, R.sub.2 is alkyl of 1 to 6 carbon atoms, m is an integer from 6 to 15, and each of r and s is 1 or 2, or a copolymer of the above monomers and further ethylenically unsaturated monomers, optionally in admixture with further homo- or copolymers and/or monomeric compounds. The furnish synthetic organic fibrous material, especially textile material, shows a permanent antistatic effect. The antisoiling effect and also the fastness to rubbing and light and the soft handle are not impared by the finish.

Method of finishing synthetic organic fibrous material, in particular of

The present invention relates to boric acid/amine reaction products of (a) boric acid and (b) an amine of the formula ##STR1## in which R denotes optionally substituted alkyl, alkenyl, aryl or cycloalkyl or an optionally substituted heterocyclic radical and m and n are each a number from 1 to 6. These products are used as auxiliaries in the textile, leather, detergent and cosmetics industry.

Boric acid/amine reaction products, their manufacture and use

Heterocyclic nitrogen compounds of the formula ##STR1## ARE PROVIDED, WHEREIN R is a succinimide, maleinimide, or phthalimide radical or a lactam radical containing 5 to 11 --(CH.sub.2)-- groups in the heterocyclic ring, R.sub.1 is hydrogen or C.sub.n H.sub.2n+1 and n is an integer from 1 to 24. These compounds are useful for finishing synthetic organic fibrous material, in particular for providing it with an antistatic finish and optionally improving the dirt repellency, optionally in admixture with polymers; said compounds or mixtures are applied to the fibrous material from aqueous or organic solutions or from emulsions, and subsequently dried at elevated temperature.

Heterocyclic nitrogen compounds, process for their manufacture and their

New bromine compounds are provided. They correspond to the formula

Bromine substituted carboxylic acid esters

A process for the manufacture of perfluoroalkyl iodide adducts is provided, wherein a perfluoroalkyl iodide is reacted with an olefine in the presence of an amine and a metal salt of groups Ia to IVa or Ib to VIIIb of the periodic system, the amine and metal salt optionally being in the form of an amine-metal salt complex. The end product optionally may be deiodized. The adducts may be used as intermediates for the manufacture of products used for finishing textiles, paper or leather and other solids, especially for rendering such substrates oleophobic or hydrophobic.

Process for the manufacture of perfluoroalkyl iodide-olefine adducts

A method of finishing synthetic organic fibrous material, in particular of providing such material with an antistatic finish and simultaneously improving the dirt repellency is provided, which comprises treating said material with aqueous or organic solutions or emulsions which contain

Dialkylphosphonopropionic acid amides of formula ##STR1## WHEREIN R is a straight-chain or branched alkyl radical of 1 to 8 carbon atoms, R.sub.1 is hydrogen or methyl, R.sub.2 is hydrogen or C.sub.n H.sub.2n.sub.+1 and n is an integer from 1 to 24, are provided. These compounds are useful for finishing synthetic organic fibrous material, in particular for providing it with an antistatic finish and optionally for simultaneously improving the dirt repellency, when applied in admixture with further monomeric compounds or with polymers; said compounds or mixtures are applied to the fibrous material from aqueous or organic preparations and the fibrous material is subsequently dried at elevated temperature.

Dialkylphosphonopropionic acid amides and process for their manufacture

The present invention provides new perfluoroalkylcarboxylic acid esters of the formula ##STR1## WHEREIN R.sub.f is perfluoroalkyl with 4 to 18 carbon atoms, A represents a radical forming with the --NCO--N-group ethylene urea, hydantoin or isocyanurate radicals, m is a whole number from 1 to 3, q is 1 or 2 and x is 0, 1 or 2, with x being 0 or 1 if m is 1. The new compounds are useful for producing oil- and water-repellent finishes on porous and non-porous finishes, such as paper, textiles or plastics.

N-imidazolidinone perfluoroalkylcarboxylic acid ester

New perfluoroalkylalkylcarboxylic acids of the formula ##EQU1## are provided, wherein R.sub.f is an unbranched or branched perfluoroalkyl radical with 3 to 18 carbon atoms, R.sub.1 is hydrogen or fluorine and m is a whole number from 1 to 3. The new compounds are suitable for producing water and oil-repellent finishes, soil-release and antisoiling effects on porous and non-porous substrates. They are further valuable intermediates for the manufacture of fluorinated compounds which may be used in the same field as the inventive compounds.

Perfluoroalkylalkylcarboxylic acids, process for their manufacture and

New polyfluoroalkyl iodides of the formula ##EQU1## are provided, wherein R.sub.f represents a fluorinated hydrocarbon radical with 3 to 18 carbon atoms, R.sub.1 represents hydrogen or fluorine, R.sub.3 and R.sub.4 each independently represents hydrogen, lower alkyl, hydroxyalkyl, carboxy, carbalkoxy, --(CH.sub.2).sub.p OCOR.sub.2, in which R.sub.2 represents hydrogen or alkyl with 1 to 3 carbon atoms and p is 0 or a whole number from 1 to 3, phenyl and alkylphenyl, or R.sub.3 and R.sub.4 together with the carbon atoms to which they are bonded represent an optionally substituted cycloaliphatic radical with 5 or 6 ring carbon atoms, and n is a whole number from 1 to 3. The new compounds are useful as intermediates for the manufacture of oil- and water-repellents, as oil- and water-repellents per se, as lubricants and as surface active assistants.

Polyfluoroalkyl iodides, process for their manufacture, and their use

The present invention provides new perfluoroalkylcarboxylic acid esters of the formula ##EQU1## WHEREIN R.sub.f is perfluoroalkyl with 4 to 18 carbon atoms, A represents a radical forming with the --NCO--N-group ethylene urea, hydantoin or isocyanurate radicals, B is --O-- or --OH Cl-- , m is a whole number from 1 to 3, q is 1 or 2 and x is 0, 1 or 2, with x being 0 or 1 if m is 1. The new compounds are useful for producing oil and water-repellent finishes on porous and non-porous finishes, such as paper, textiles or plastics.

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Bettingen, Switzerland

Horst H Jager