Chromogenic quinazolines

C - Chemistry – Metallurgy – 07 – D

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C07D 239/72 (2006.01) B41M 5/136 (2006.01) B41M 5/323 (2006.01) C07D 239/74 (2006.01) C07D 239/86 (2006.01) C07D 239/91 (2006.01) C07D 239/94 (2006.01) C07D 403/00 (2006.01)

Patent

CA 1162193

Abstract Chromogenic quinazolines of the formula (1) Image wherein Y is an amino-substituted phenyl radical of the formula Image (1a) or a 3-carbazolyl radical of the formula (1b) Image and Z is hydrogen, R1, -OR?, -SR? or -NR2R3, whilst R is hydrogen, alkyl of at most 12 carbon atoms which is unsubstieuted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or is alkenyl of at most 12 carbon atoms, acyl of 1 to 12 carbon atoms, benzyl, or benzyl which is substituted by halogen, nitro, lower alkyl or lower alkoxy; each of R1 and R? is alkyl of at least 12 carbon atoms which - 2 - is unsubstituted or substituted by cyano or lower alkoxy, or is cycloalkyl, unsubstituted or substituted aryl or aralkyl or an unsubstituted or a substituted heterocyclic radical, and R? is also halogen of 2 to 6 carbon atoms; each of R2, R3, X1 and X2 independently is hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted halogen, hydroxyl. cyano or lower alkoxy. or is cycloalkyl, phenyl, benzyl, or phenyl or benzyl each of which is sub- stituted by halogen, nitro, cyano, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and R2 is also acyl of 1 to 12 carbon atoms, or each pair of substituents (R2 and R3) and (X1 and X2), together with the nitrogen atom to which said pair is attached, independently is a 5- or 6-membered heterocyclic radical; X3 is hydrogen. halogen, nitro, lower alkyl or lower alkoxy; and each of the rings A, B and D independently is unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, lower alkoxy or lower alkoxy- carbonyl, and the ring D can also contain an unsubstituted or a substituted phenyl radical or a fused benzene ring. These compounds are particularly suitable for use as colour formers in pressure-sensitive or heat-sensitive recording materials and give lightfast yellow, orange and red colorations.

369639

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