Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

John Barry Henshall

John Whitworth

Robert Garner

James Philip Taylor

Michael Heneghan

Jean-Claude Petitpierre

Malcolm C Clark

Roy Alan Kirk

Ian Antony Dearden

Robert M O'Neil

Davor Bedekovic

Jerry L Pool

Brian J Williams

Jonathon Gawtrey

Steven Walsh

Derrick A Hart

Heat sensitive recording material

Disclosed are a novel crystal form of the fluoran compound represented by formula (I) as characterised by specific X-ray powder diffraction pattern and melting range; process for the preparation of said novel crystal form and recording materials comprising the said crystal form.

Crystalline fluoran compound

The invention provides a process for the preparation of 3-(N,N-dimethylamino)benzoic acid which comprises subjecting an aqueous solution of an alkali metal salt or ammonium salt of 3-aminobenzoic acid to reductive methylation in the presence of a supported transition metal catalyst, by the controlled and continuous addition of a solution of formaldehyde over a period of 0.5 to 20 hours with a hydrogen pressure between 1 bar and 40 bar and with the temperature of the reaction mass gradually raised during the reduction, the reaction being carried out within the temperature range of 20.degree. C. to 120.degree. C., and wherein a buffering agent is added such that the pH of the reaction mass after reductive methylation is from 6.5 to 9.5.

Chemical process

A method for the purification of a keto acid having the general formula ##STR1## wherein R1 and R2 independently represent a straight or branched chain alkyl of 1-18 carbon atoms, a cycloalkyl of 4-8 carbon atoms or a phenyl both of which may be substituted by at least one substituent selected from the group consisting of halogen atoms and alkyls having 1-4 carbon atoms, an aralkyl of 7-10 carbon atoms, alkoxyalkyl having 2-20 carbon atoms, tetrahydrofuryl alkyl, alkylcarboxy alkyl, alkyl carboxy benzyl, or R1 and R2 together with the adjacent nitrogen atom may form a heterocyclic ring, or one of R.sub.1 and R.sub.2 is hydrogen, which comprises slurrying the keto acid with an alcohol solvent, maintaining the slurry at elevated temperature in a sealed vessel until the Rhodamine impurity has dissolved, cooling and isolating the pure keto acid by filtration.

Purification process

A method of producing N,N-disubstituted aminophenols of the general formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represents a saturated or unsaturated aliphatic hydrocarbyl, cycloalkyl, aralkyl, the phenyl ring of which may be further substituted, alkoxyalkyl, or a cycloalkylalkyl, except that R.sub.1 and R.sub.2 are not simultaneously methyl and R' represents hydrogen, halogen, nitro, cyano, alkyl or alkoxy, which comprises reacting an aminophenol of general formula ##STR2## wherein R.sub.3 represents hydrogen or R.sub.1, and R' is as defined above, with an organic halide species of general formula R.sub.2 X wherein R.sub.2 is as defined above and X is halogen under aqueous acidic conditions with the periodic addition of an acid trapping agent in such a way that continuous monitoring of pH is not required.

Production of aminophenols

A process for the preparation of a fluoran compound of the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy,

Process for the manufacture of fluoran compounds

A process for the production of a compound of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds (2a) and (2b) with a compound ZH or a compound of formula ##STR3## or a mixture of the compounds (2c) and (2d) with a compound YH, both reactions under acidic conditions, wherein X and Y are the same or different and each represents an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para position to the indicated bond, or a heterocyclic group, and Z represents an aryl radical of formula ##STR4## wherein R.sub.1 and R.sub.2 independently of one another represent hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, or substituted alkyl, cycloalkyl, aralkyl or aryl, or R.sub.1 and R.sub.2 together with the nitrogen atom which links them represent a five- or six-membered, preferably saturated, heterocyclic radical and

Process for the production of triaryl methane compounds

A process for the production of a sulphinate of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds of formulae (2a) and (2b) with a compound of formula

Process for the production of sulphinates of benzhydrol compounds

Indolyl methylene leuco dyestuffs of the formula ##STR1## wherein X.sub.1 and X.sub.2 independently of the other, represent alkyl with 2 to 12 carbon atoms, alkenyl with at most 12 carbon atoms or phenylalkyl with 1 to 4 carbon atoms in the alkyl part, Y.sub.1 and Y.sub.2 independently of the other, represent hydrogen, alkyl with 1 to 12 carbon atoms or phenyl, Z represents alkyl with 1 to 12 carbon atoms, alkenyl with at most 12 carbon atoms, aryl, aralkyl or a heterocyclic residue and the rings A and B may be further substituted by cyano, nitro, halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or acyl with 1 to 8 carbon atoms, said methylene compounds are particularly useful as slow developing color formers in pressure-sensitive recording material and exhibit good light and air stability.

Indolyl methylene leuco dyestuffs

Pressure-sensitive copying material containing included in its Color-reactant system a mixture of at least two color formers, wherein at least one color former is a leuco methylene dyestuff of the formula ##EQU1## wherein Y represents an amino-substituted phenyl residue of the formula ##SPC1## Or an indolyl residue of the formula ##SPC2## Wherein R.sub.1 and R.sub.2, independently of the other represent hydrogen, alkyl with 1 to 12 carbon atoms, alkoxyalkyl with 2 to 8 carbon atoms, benzyl or phenyl, R.sub.3 is hydrogen, halogen, nitro, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms, X.sub.1 represents hydrogen, alkyl with 1 to 12 carbon atoms, alkenyl with at most 12 carbon atoms or benzyl, X.sub.2 represents hydrogen, alkyl with 1 to 12 carbon atoms or phenyl and the ring A is unsubstituted or substituted by cyano, nitro, halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or acyl with 1 to 8 carbon atoms, and Z represents alkyl with 1 to 12 carbon atoms, alkenyl with at most 12 carbon atoms, aryl, aralkyl, an heterocyclic radical or the residue of an organic, particularly aliphatic or cycloaliphatic compound having a ketomethylene group.

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Manchester, United Kingdom

John Barry Henshall