GB1470552A - Colour photographic light-sensitive emulsions - Google Patents

Abstract

1470552 5-Pyrazolones FUJI PHOTO FILM CO Ltd 20 May 1974 [19 May 1973] 22483/74 Heading C2C [Also in Division G2] The invention comprises a 5-pyrazolone coupler of formula I wherein R<SP>1</SP> represents a hydrogen atom, an aliphatic group; an optionally substituted aryl group or a heterocyclic group; R<SP>2</SP> represents an alkyl an optionally substituted aryl, a heterocyclic, an alkoxycarbonyl, an aryloxycarbonyl, aralkyloxycarbonyl, alkoxy, aryloxy, alkylthio, arylthio, carboxyl, amino, amido, N-alkylacylamino, N-arylacylamino, ureido, thioureido, carbamyl, sulphamyl, piperidino, pyrrolidino or guanidino group; A<SP>1</SP> represents an optionally substituted alkyl, aryl or heterocyclic group, A<SP>2</SP> represents hydrogen or any group that A<SP>1</SP> may represent, or A<SP>1</SP> and A<SP>2</SP> together complete a 5- or 6-membered heterocyclic ring which may be fused to a saturated or unsaturated condensed ring except when A<SP>1</SP> and A<SP>2</SP> together complete a piperidine or fused piperidine ring and subject to the proviso that the ring does not have an aromatic ring condensed therewith in the cases (i) when the ring completed by A<SP>1</SP> and A<SP>2</SP> includes a total of three or more nitrogen atoms, and (ii) when the ring completed by A<SP>1</SP> and A<SP>2</SP> is a diazole ring. The compounds can be prepared by the method given in Specification 1,457,056. In example 1 - (2,4,6 - trichlorophenyl) - 3 - {3 - [(2,4 - ditert - amylphenoxy)acetamido]benzamido} - 4- piperidino-5-pyrazolone is prepared by hydrogenation of the corresponding -4-pyridiniocompound in the presence of Raney nickel. 1 - (2,4,6 - Trichlorophenyl) - 3 - [2 - chloro - 5- (n - tetradecaneamido)anilino]- 4 - piperidino- 5-pyrazolone is prepared similarly. In other specific compounds listed (Couplers 3 to 22) the substituents are variously, at the 1-position:- 2,4,6 - trichlorophenyl, 2,6 - dichloro - 4 - methoxy, methyl- or carboxy-phenyl, 4-acetoaminophenyl, 4 - (2,4 - di - tertamylphenoxy)acetoamido - phenyl, 4 - (α - (2,4 - di - tertamylphenoxy)butyramido]phenyl; at the 3 -position:- 3 - [α - (2,4 - di - tert - amylphenoxy) - butyramido] - benzamido, 3 - [(2,4 - di - tert - amylphenoxy)acetoamido] - benzamido, 3 - [γ - (3 - npentadecylphenoxy)butyramido]phenylureido , 2 - chloro - 5 - [γ - (2,4 - di - tert - amylphenoxy)- butylsulphonamido]anilino, benzamido ethoxy, 2 - chloro - 5 - n - tetradecyloxy - carbonylanilino, 2 - chloro - 5 - carboxy - anilino, cyclohexylamino, 2 - chloro - 5 - tetradecaneamidoanilino; at the 4 - position: -piperidino, 3- ethyl - 4 - methyl - piperidono, 4 - n - propylpiperidino, 1,2,3,4 - tetrahydroisoquinolyl, 4- methylpiperidino, 4 - n - tetradecyl - piperidino, 3 - ethyl - 4 - methylpiperidino, 4 - chloropiperidino, N - morpholino, N - 1,2,3,4 - tetrahydro- 5 - azaquinolyl, 2 - chloro - 4 - n - tetradecylpiperidino, indolyl, N - phthalimido, imidazolyl. Coupler 15 is 1,4 - bis[1 - (2,4,6 - trichlorophenyl) - 4 - piperidino - 5 - pyrazolonyl - (3)]- terephthalamide.