Ciba-Geigy Corporation

Rox Phaff

Davor Bedekovic

Rudolf Zink

Hans Baumann

The invention relates to chromogenic lactams, to their preparation and to the use thereof in pressure-sensitive or heat-sensitive recording materials. The novel lactams have the general formula I ##STR1## wherein the ring A is an aromatic or heteroaromatic radical containing 6 ring atoms;

Chromogenic lactams

Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,

Pyran-containing phthalides

Pyrroline- or indoline-containing phthalides of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other lower alkyl, C.sub.5 -C.sub.7 cycloalkyl or benzyl or, when taken together, are C.sub.4 -C.sub.6 alkylene,

Indoline-containing phthalides

Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower)alkoxycarbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower) alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinozaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.4) are each, independently of each other, together with the nitrogen atom joining them, a five- or six-membered, heterocyclic radical,

Chromogenic phthalides and azaphthalides

A pressure-sensitive or heat-sensitive recording material in which the color reactant system contains, as main components (A) a polycyclic compound of the formula ##STR1## in which X is a monocyclic or polycyclic aromatic or heteroaromatic radical,

Pressure-or heat-sensitive recording material

Pressure-sensitive or heat-sensitive recording material in which the color reactant system contains, as essential components,

Pressure- or heat-sensitive recording material

Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.4) are each, independently of each other, together with the nitrogen atom joining them, a five- or six-membered, heterocyclic radical,

Chromogenic 1-heterocyclic substituted 2,4-benzoxazines of formula ##STR1## wherein X.sub.1 and X.sub.2 are identical or different monocyclic or polycyclic heteroaromatic radicals and X.sub.2 is also an aryl radical, Y is hydrogen, alkyl, cycloalkyl, aryl, aralkyl or a heterocyclic radical, and the benzene ring A is substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, lower alkylthio, lower alkylcarbonyl, lower alkoxycarbonyl or --NR.sub.1 R.sub.2, in which R.sub.1 and R.sub.2 are each independently of the other hydrogen, alkyl of not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano or lower alkoxy, or are cycloalkyl of 5 to 10 carbon atoms, or phenalkyl or phenyl, each unsubstituted or ring-substituted by halogen, cyano, lower alkyl or lower alkoxy, or --NR.sub.1 R.sub.2 is a 5- or 6-membered, preferably saturated, heterocyclic radical. These benzoxazines are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording materials and give strong and lightfast orange, pink, red, violet, green, greenish-blue, violet blue, grey or black colorations.

Chromogenic 1-heterocyclic substituted 2,4-benzoxazines

Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.4) are each, independently of each other, together with the nitrogen atom joining them, a five- or six-membered, heterocyclic radical, Y.sub.1 is hydrogen, lower alkyl, cycloalkyl, phenalkyl or phenyl, Y.sub.2 is hydrogen, lower alkyl or phenyl, Z.sub.1 and Z.sub.2 are each, hydrogen, unsubstituted or halogen-, hydroxyl-, cyano- or (lower alkoxy)-substituted alkyl acyl or unsubstituted or substituted benzyl, X is hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.12 -acyloxy, benzyl, phenyl, benzyloxy, phenyloxy, halogen-, cyano-, (lower alkyl)- or (lower alkoxy)-substituted benzyl or benzyloxy, or the group --NT.sub.1 T.sub.2, T.sub.1 and T.sub.2 are each, independently of the other, hydrogen, lower alkyl, cycloalkyl, unsubstituted or substituted benzyl or acyl and T.sub.1 is also unsubstituted or substituted phenyl, and the benzene nucleus D is unsubstituted or substituted. These phthalides and azaphthalides are suitable in particular for use as color formers in pressure- or heat-sensitive recording materials and produce green, greenish blue, greyish blue, blue or violet-blue colors.

Growing community of inventors

Itingen, Switzerland

Rox Phaff