Ciba-geigy Corporation

Ian R Wheeler

George H Robertson

James M McCrae

Ian Alexander Macpherson

John Andrew Stirling

David McGregor

A process for the production of an azo compound comprising contacting with agitation a solution or dispersion of a diazotizable amine, a solution or dispersion of a coupling component and an organic or inorganic nitrite compound, in a water insoluble liquid organic acid, adding to the reaction mixture so formed aqueous alkali to transfer the organic acid, as its soluble salt, into the aqueous phase and separating the azo compound from the liquors. The azo compounds are produced in high yield and purity and are suitable for use as pigments and disperse dyes.

Production of azo compounds

A process for conditioning pigments which comprises grinding a crude copper phthalocyanine pigment and a crystallizing solvent in the absence of inorganic salt but in the presence of one or more sulphonated phthalocyanine amine derivative having the general formula ##STR1## wherein Pc is a phthalocyanine, R.sup.1, R.sup.3 and R.sup.4 are hydrogen or a hydrocarbon residue, R.sup.2 is a hydrocarbon residue, p is 0 to 3, q is 1 to 4, and the sum of p and q is 1 to 4, the resulting pigment composition is freely dischargeable from the mill in high yield and is, moreover largely in the .beta.-form.

Process for conditioning phthalocyanine pigment

A process for producing a pigment or dyestuff composition in the form of dustless readily dispersible granules, which process comprises contacting, with agitation, an aqueous dispersion of a pigment and a composition comprising one or more organic acids which are liquid at temperatures below 100.degree. C. or their salts, at a pH value at which the acid is insoluble in water, the temperature being maintained during contacting above the melting point of the acid until the pigment has completely transferred into the organic phase; increasing the pH to a value suitable to render the acid soluble in water and recovering the resulting granules.

Process for the preparation of dustless, readily-dispersible pigment or

A pigment composition comprising 80-99% weight/weight of copper phthalocyanine containing 1.5-10% weight/weight of peripherally-bound chlorine, and 20-1% weight/weight of a sulphonated copper phthalocyanine derivative having the formula: ##STR1## wherein CuPc represents a copper phthalocyanine residue, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms or a cyclic alkyl group having from 5 to 22 carbon atoms, an aryl,aralkyl,alkaryl or dehydroabietyl group, X represents hydrogen or an alkali metal atom and m, n and p can each be 0 or a value in the range of from 1 to 4, with the proviso that the sum of m, n and p is within the range of from 1 to 4; the composition being characterized by its x-ray diffraction spectrum as resembling the .gamma.--crystal form, and further characterized by the substantial absence of any tendency to crystallize on prolonged contact with aromatic solvents, even at elevated temperatures, which composition, without further pigmentization stages, is suitable for direct incorporation in surface coating media, and provides excellent strength and flow properties therein.

Pigment compositions

A process for the manufacture of substantially dust free meterable and readily dispersible beads of a pigment composition which comprises contacting with agitation a suspension of a finely divided pigment or pigment composition in a mixture of water and an oxygenated aliphatic hydrocarbon solvent containing from 1 to 5 carbon atoms and having appreciable solubility in water, together with a solution of a carrier which is substantially water insoluble and soluble in the respective solvent at reflux temperature and then distilling off the solvent and recovering the resultant beads by filtration from the aqueous phase.

Pigment compositions and process for dust free pigment beads

A process for the preparation of a solvent-stable, red shade copper phthalocyanine pigment composition by reacting an organic compound capable of forming the phthalocyanine ring system, benzophenone 3,3',4,4'-tetracarboxylic acid or a derivative thereof, a copper compound capable of providing the copper atom of the copper phthalocyanine molecule, a reaction catalyst, and a nitrogen source, optionally in the presence of at least one phthalocyanine compound substituted by 1 to 4 groups of a sulphonate or sulphonic acid and/or sulphonamide which may be N-substituted.

Process for the preparation of a solvent-stable, red-shade copper

A single stage process for the production of copper phthalocyanine pigment compositions having x-ray diffraction spectra corresponding to the form of pure, or substantially pure .epsilon.-crystal modification of copper phthalocyanine comprising reacting, at an elevated temperature and in an organic solvent, an organic compound capable of forming the phthalocyanine ring system, a copper compound capable of providing the copper atom of the phthalocyanine molecule, a reaction catalyst, and a nitrogen source, in the presence of, as crystal form modifier, a compound of the formula: ##STR1## where Pc represents a copper phthalocyanine residue, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different and each is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl, aralkyl, alkaryl, cycloalkaryl or dehydroabietyl group, the alkyl and cycloalkyl groups being optionally unsaturated and/or interrupted by heteroatoms, M represents hydrogen or an alkali metal atom and x, y and z are each in the range of from 0 to 4 with the proviso that the sum of x, y and z is within the range of from 1 to 4. Very red shade copper phthalocyanine pigment compositions of the advantageous .epsilon.-modification can be produced in a single stage without the use of high shear forces.

Pigment composition

A phthalocyanine pigment composition comprising a phthalocyanine pigment and a sulphonated phthalocyanine derivative of the formula

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Houston, United Kingdom

Ian R Wheeler