Ciba-geigy Corporation

Ciba-geigy Ag

Other

Jean C Petitpierre

Robert Garner

Peter Burri

Heinz Balli

Sigmund Gunzenhauser

Hermann Nachbur

Stefan Koller

Visvanathan Ramanathan

Albert Wurmli

Hans U Brechbuhler

A pressure- or heat-sensitive recording material which, in its color reactant system, contains as a color developer for the color former, at least one substituted resorcinol compound of the formula ##STR1## or a corresponding zinc or aluminium salt, in which R is a carboxyl- or aroyl-free substituent which has a positive Hammett para-sigma value and which is capable of forming, together with the adjacent hydroxyl group, an intramolecular hydrogen bond in the form of a six-membered ring.

Pressure-sensitive or heat-sensitive recording material

Chromogenic compounds of the formula ##STR1## wherein each of Y.sub.1 and Y.sub.2 independently represents an aminosubstituted phenyl radical of the formula ##STR2## a 3-indolyl radical of the formula ##STR3## a 3-carbazolyl radical of the formula ##STR4## and Q represents alkyl of 1 to 12 carbon atoms or unsubstituted or substituted aryl or aralkyl, while each of X.sub.1 and X.sub.2 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or X.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical, X.sub.3 represents hydrogen, halogen, nitro, lower alkyl or lower alkoxy, each of R and Z.sub.1 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents alkenyl containing not more than 12 carbon atoms, acyl of 1 to 12 carbon atoms, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl, lower alkoxy or nitro, and Z.sub.2 represents hydrogen, lower alkyl or phenyl, and the rings A, B and D, each independently of the other, can be unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring D can also contain an unsubstituted or substituted phenyl radical or a fused benzene ring. These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording materials.

Chromogenic propenylenesulfone compounds

Carbazolylmethane compounds of the formula ##STR1## wherein one of Y.sub.1, Y.sub.2 and Q represents a 3-carbazolyl radical of the formula ##STR2## and each of the other two independently represents an amino-substituted phenyl radical of the formula ##STR3## a 3-indolyl radical of the formula ##STR4## These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording material.

Carbazolylmethane compounds

Fluoran compounds of the formula ##STR1## wherein one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents n-alkyl having 6 to 12 carbon atoms and the other R's, independently of each other, represent hydrogen, alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms or benzyl optionally substituted in the ring by nitro, halogen or alkyl having 1 to 6 carbon atoms. The fluoran compounds are particularly useful as color formers which give intense dark green color when they are brought into contact with an electron-accepting co-reactant.

Copying material employing fluoran color formers

A pressure-sensitive or heat-sensitive recording material which comprises in its color reactant system, as developer for the color former, at least one compound of the formula ##STR1## wherein the ring Z is a heterocyclic radical which does not contain a keto group adjacent to the linking carbon atom, X is the direct bond, --O--, --CHR--, --NR--, --CONR--, --SO.sub.2 NR--, --Nr.sub.1 --CO--NR.sub.2 --,--NR.sub.1 --CS--NR.sub.2 -- or --NR.sub.1 --SO.sub.2 --NR.sub.2 --, wherein each of R, R.sub.1 and R.sub.2 independently is hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, cyano or lower alkoxy, or is benzyl, phenyl, or benzyl or phenyl each of which is substituted by halogen, methyl or methoxy, Q is carbon or an unsubstituted or substituted hydrocarbon radical, Y is halogen and m is 1 to 3. The grouping --O--Y.sub.m is preferably --C(Hal).sub.3, wherein Hal is halogen.

A benzopyranothiazole of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently represents hydrogen, alkyl of not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or a N-carbazolyl radical, Q represents hydrogen, lower alkyl, benzyl or groups of the formulae (1a) or (1b) ##STR2## each of X, X.sub.1 and X.sub.2 represents hydrogen, halogen, lower alkyl or lower alkoxy, each of Y.sub.1, Y.sub.2, Y'.sub.1 and Y'.sub.2 represents hydrogen, alkyl of not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or each of the pair of substituents Y.sub.1 and Y.sub.2 and Y'.sub.1 and Y'.sub.2, together with the nitrogen atom to said pair is attached, independently represents a 5- or 6-membered heterocyclic radical or a N-carbazolyl radical and the ring A is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, phenoxy or an amino group which is unsubstituted or substituted by lower alkyl, phenyl or benzyl; these compounds are particularly useful as color formers which give intense red to blue color shades of excellent light fastness when they are brought into contact with an electron-accepting co-reactant.

Benzopyranothiazoles

A pressure-sensitive or heat-sensitive recording material which contains in its color reactant system, as developer for the color former, at least one compound of the formula ##STR1## wherein X is the direct bond or ##STR2## each of R.sub.1, R.sub.2 and R.sub.3 independently is hydrogen or unsubstituted or substituted alkyl, aryl or aralkyl, or R.sub.1 and R.sub.3, together with the nitrogen atom to which they are attached, are a 5- or 6-membered heterocyclic radical, Q is carbon or an unsubstituted or substituted hydrocarbon radical, Y is halogen, and m is 1 to 3. The grouping --Q--Y.sub.m is preferably --C(Hal).sub.3, wherein Hal is halogen.

Fluoran compounds

A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,

3-Indolyl-3-bis-amino-phenyl-phthalide compounds

A pressure-sensitive or heat-sensitive recording material which contains in its color reactant system, as developer for color formers, at least one compound of the formula ##STR1## wherein Z is the radical of a reactive organic methylene or methyl compound or a radical of the formula ##STR2## wherein each of A.sub.1 and A.sub.2 independently is carbon or unsubstituted or substituted alkylene, arylene or aralkylene, each of X.sub.1 and X.sub.2 is halogen, cyano or nitro, each of D.sub.1, D.sub.2 and E independently is unsubstituted or substituted alkyl, aralkyl, aryl, alkanoyl, alkylsulfonyl, aroyl, arylsulfonyl, cyanoamidino, or is the group ##STR3## wherein each of R.sub.1 and R.sub.2 independently is hydrogen or unsubstituted or substituted alkyl, aryl or aralkyl, whilst D.sub.1 and D.sub.2 are also hydrogen, or each of the pairs of substituents (R.sub.1 and R.sub.2) and (D.sub.1 and E) together with the nitrogen atom to which said pair is attached is a 5- or 6-membered heterocyclic radical, W is --CO--, --SO.sub.2 --, --COCO--, ##STR4## or unsubstituted or substituted alkylene or phenylene, G is unsubstituted or substituted alkyl, aralkyl or aryl or is a 5- or 6-membered heterocyclic radical, and m is 1 to 6.

Chromogenic compounds of the formula ##STR1## wherein each of Y.sub.1 and Y.sub.2 independently represents an amino-substituted phenyl radical of the formula ##STR2## a 3-indolyl radical of the formula ##STR3## or a 3-carbazolyl radical of the formula ##STR4## and Q represents alkyl of 1 to 12 carbon atoms or unsubstituted or substituted aryl or aralkyl, while each of X.sub.1 and X.sub.2 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or X.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical, X.sub.3 represents hydrogen, halogen, nitro, lower alkyl or lower alkoxy, each of R and Z.sub.1 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents alkenyl containing not more than 12 carbon atoms, acyl of 1 to 12 carbon atoms, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl, lower alkoxy or nitro, and Z.sub.2 represents hydrogen, lower alkyl or phenyl, and the rings A, B and D, each independently of the other, can be unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring D can also contain an unsubstituted or substituted phenyl radical or a fused benzene ring. These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording materials.

A pressure- or heat-sensitive recording material which contains as color former at least one 2,2-diarylchromeno compound of the formula ##STR1## wherein V.sub.1 and V.sub.2, each independently of the other, represent hydrogen, halogen, lower alkyl or lower alkoxy,

Pressure-sensitive or heat-sensitive recording material and novel

Carbazolylmethane compounds of the formula ##STR1## wherein one of Y.sub.1, Y.sub.2 and Q represents a 3-carbazolyl radical of the formula ##STR2## and each of the other two independently represents an amino-substituted phenyl radical of the formula ##STR3## a 3-indolyl radical of the formula ##STR4## a 3-carbazolyl radical of the formula ##STR5## or a 3-carbazolyl radical of the formula (1a), and Q also represents hydrogen, alkyl of 1 to 12 carbon atoms, alkenyl containing not more than 12 carbon atoms, aryl, aralkyl or a further heterocyclic radical, while each of X.sub.1 and X.sub.2 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or X.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical, X.sub.3 represents hydrogen, halogen, nitro, lower alkyl, or lower alkoxy, each of R.sub.1, R.sub.2 and Z.sub.1 independently represents hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents alkenyl containing not more than 12 carbon atoms, acyl of 1 to 12 carbon atoms, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl, lower alkoxy or nitro, and Z.sub.2 represents hydrogen, lower alkyl or phenyl, the ring A is substituted by phenyl or at least one fused benzene nucleus, and the phenyl radical, the fused benzene nucleus and the rings B, D, E and G, each independently of the other, are unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl; these compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording material.

Thiazolylphthalide compounds of the general formula ##STR1## wherein A represents a p-aminophenyl readical of formula ##STR2## or a 3-indolyl radical of formula ##STR3## or a 2-thiazolyl radical of formula ##STR4## each of R.sub.1, R.sub.2, X.sub.1, X.sub.2, R.sub.1 ' and R.sub.2 ' independently represents hydrogen, alkyl of 1 to 12 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms, cycloalkyl of 5 or 6 carbon atoms, or unsubstituted or substituted benzyl or phenyl, or

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Kaiseraugst, Switzerland

Jean C Petitpierre