Pyrazolone couplers and colour photographic silver halide recording material containing them

Claim 2

A pyrazolone colour coupler of the formula wherein X is -S-, -0- or -Se-, R is hydrogen, chlorine, bromine or iodine or optionally substituted alkyl, phenyl, alkoxy, phenoxy, acyloxy, alkylthio or phenylthio, R 2 is -CO-alkyl, -CO-C 6 H 5 , -CONH-C 6 H 5 , -CONH-alkyl, -SO 2 -alkyl or -SO 2 -C 6 H 5 , wherein the alkyl and C 6 H 5 -radicals are optionally substituted, R 3 is alkyl, phenyl, -NH-alkyl, -NH-C 6 H 5 , -NHCONH-alkyl, -NHCONH-C 6 H 5 , -NHCO-C 6 H 5 or -NHCO-alkyl, wherein the alkyl and C 6 H 5 -radicals are optionally substituted, R 4 is hydrogen or substituted alkyl or phenyl, at least in one of the alkyl or phenyl groups of R 3 or R 4 being present a ballasting group B.

Claim 3

A pyrazolone colour coupler according to claim 1, wherein R 1 is hydrogen, chlorine, bromine or iodine or alkyl, alkoxy or alkylthio, wherein the alkyl moiety contains 1 to 6 carbon atoms, or phenyl, phenoxy, phenylthio or carboxylic acid acyl, R 2 is -CO-alkyl, -CONH-alkyl or -SO 2 -alkyl, wherein the alkyl moiety contains 1 to 6 carbon atoms, or - C 6 H 5 , -CO-C 6 H 5 , -CONH-C 6 H 5 or -SO 2 -C 6 H 5 , and wherein the alkyl and phenyl moieties are unsubstituted or substituted by alkyl or hydroxyalkyl, carbalkoxy, -NHCO-alkyl or halogen, the alkyl radicals containing 1 to 4 carbon atoms, R 3 is alkyl, -NH-alkyl or -NHCONH-alkyl, the alkyl moieties containing 1 to 6 carbon atoms, or phenyl, -NH-C 6 H 5 , -NHCONH-C 6 H 5 or -NHCO-C 6 H 5 , wherein phenyl and the alkyl moieties are unsubstituted or substituted by halogen, cyano, hydroxyalkyl, carbalkoxy, -CONH-alkyl or -NHCO-alkyl, the alkyl radicals containing 1 to 6 carbon atoms, R is hydrogen, alkyl having 1 to 6 carbon atoms or phenyl, where the alkyl moieties and phenyl are substituted by halogen, alkyl, hydroxyalkyl or carbalkoxy, the alkyl moiety containing 1 to 4 carbon atoms, or -SO 2 NHR 5 , -NHCOR 5 or -NHSO 2 R 5 , wherein R is alkyl having 1 to 6 carbon atoms or phenyl, which radicals are unsubstituted or substituted by methoxy, ethoxy or halogen, at least one of the alkyl or phenyl groups of R or R being a ballasting group B, and X is as defined in claim 1.

Claim 4

A pyrazolone colour coupler according to claim 2, wherein X is -0- or -S-, R 1 is alkyl or alkoxy, wherein the alkyl moiety contains 1 to 6 carbon atoms, or phenyl or phenoxy, R 2 is -CO-alkyl or -SO 2 -phenyl, wherein phenyl and the alkyl moieties are unsubstituted or substituted by alkyl or hydroxyalkyl each having 1 to 4 carbon atoms, or halogen, R 3 is alkyl, phenyl, -NH-C 6 H 5 , -NHCONH-C 6 H 5 or -NHCO-C 6 H 5 , wherein phenyl and the alkyl moieties are unsubstituted or substituted by halogen, cyano, hydroxyalkyl, carbalkoxy, -CONH-alkyl or -NHCO-alkyl, the alkyl radicals containing 1 to 6 carbon atoms, R 4 is phenyl substituted by halogen, -SO 2 NHR 5 , -NHCOR 5 or -NHSO 2 R 5 , wherein R 5 is alkyl having 1 to 6 carbon atoms, at least one of the alkyl or phenyl groups of R 3 or R 4 being a ballasting group B.

Claim 5

A pyrazolone colour coupler according to claim 3, wherein B is alkyl having more than 10 carbon atoms or aryloxy substituted by tertiary alkyl groups having 4 to 8 carbon atoms.

Claim 6

A pyrazolone colour coupler according to claim 4, wherein B is alkyl having 10 to 30 carbon atoms or phenoxy substituted by tertiary pentyl groups.

Claim 7

A pyrazolone colour coupler according to claim 3 wherein X is -S-.

Claim 8

A process for the preparation of a pyrazolone colour coupler according to claim 1 which comprises reacting a pyrazolone of the formula wherein R 3 and R 4 are as defined in claim 1 and Y is chlorine or bromine, with an oxa- thia- or selenadiazole of the formula wherein R and R 2 are as defined in claim 1, in the presence of a base either in a melt or in solution or suspension in a solvent.

Claim 9

A process for the preparation of a pyrazolone colour coupler according to claim 1 which comprises reacting a compound of the formula wherein R 6 and R 7 are each hydrogen, alkyl or phenyl, and R 1 , R 2 , R 3 and X are as defined in claim 1 or groups which may be transformed into such groups, with a hydrazine of the formula wherein R 4 has the meaning assigned to it in claim 1, or is a group which may be transformed into such a group either in a melt or in a solvent, optionally in the presence of an acidic catalyst or a basic catalyst, at ambient or higher temperature.

Claim 10

A process according to claim 8, wherein the reaction is carried out in the presence of an acidic catalyst.

Claim 11

A process according to claim 9, wherein the acidic catalyst is acetic acid.

Claim 12

A process according to claim 8, wherein the process is carried out in a solvent.

Claim 13

A process according to claim 11, wherein the solvent is an unsubstituted or substituted alcohol.

Claim 14

A process according to claim 12, wherein the process is carried out at the boiling point temperature of the alcohol used.

Claim 15

Colour photographic silver halide material which comprises in at least one silver halide layer a pyrazolone colour coupler according to claim 1.