Azopyrazolone masking couplers

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a 1-phenyl-3-anilino-4-arylazopyrazolin-5-one masking coupler having formula I:

• ##STR67## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more fused rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is a carbonamido group, unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or the R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR68## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein at least one of the R.sup.1 substituents is chloride.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR69## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein m is at least 1 and each R.sup.3 contains up to three saturated carbon atoms.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR70## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein at least one R.sup.3 is present selected from the group consisting of alkyl and alkoxy, and R.sup.4 contains at least 8 carbon atoms.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR71## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein there are present at least two R.sup.1 substituents which are chlorine and at least one R.sup.2 substituent.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR72## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein at least one R.sup.1 is chlorine or alkoxy located in the position ortho to the amine function.

A photographic element comprising a support bearing a light-sensitive photographic silver halide layer having associated therewith a masking coupler having formula I:

• ##STR73## wherein each R.sup.1 and each R.sup.2 is a substituent independently selected so that the combined electron withdrawing strength is sufficient to obtain a Hammett sigma(para) sum for all the R.sup.1 and R.sup.2 substituents of at least 1.4;
• each R.sup.3 is selected from the group consisting of alkyl, alkoxy, carbonamido, and sulfonamido, or constitutes one or more annulated rings, each unsubstituted or substituted with nonaromatic groups;
• each n is 0 to 5 and m is 0 to 4;
• R.sup.4 is independently selected from the group consisting of hydroxyl, and alkoxy, carbonamido, and sulfonamido, each unsubstituted or substituted with nonaromatic groups, where R.sup.4 may be connected with R.sup.3 to form a ring;
• and
• one R.sup.3 or R.sup.4 group contains an alkyl group of at least 8 carbon atoms and which contains at least 70% of the saturated carbon atoms contained in all of the R.sup.3 and R.sup.4 groups combined provided that when R.sup.3 and R.sup.4 form a ring, the entire ring will be counted as R.sup.4 for purposes of satisfying the 70% requirement;
• and
• wherein at least one R.sup.1 is a sulfonyl or sulfonamide group located in the position para to the amine function.