US4379819A — Color-photographic recording material for the sil…

Claim 1

Independent Claim 902 words

A colour-photographic recording material for the silver dye bleach process which contains at least one diffusion-resistant, bleachable and oil-soluble monoazo dye dissolved in a high-boiling organic solvent in at least one silver halide emulsion layer or in a colloid layer adjoining the silver halide emulsion layer, and wherein the dye has the formula ##STR84## in which R 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, substituted or unsubstituted alkoxy having 1 to 16 carbon atoms, substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, substituted or unsubstituted aliphatic acyl having 2 to 5 carbon atoms, substituted or unsubstituted benzoyl, substituted or unsubstituted carbalkoxy having 2 to 20 carbon atoms or --NV 1 COU 1 , in which V 1 is hydrogen or alkyl having 1 to 4 carbon atoms and U 1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, or R 1 is N-alkyl-substituted or N,N-dialkyl-substituted carboxamido or sulfonamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted further, or R 1 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone, substituted or unsubstituted aryloxy or substituted or unsubstituted arylsulfonic acid ester, or is hydroxyl, cyano, nitro or halogen, R 2 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 8 carbon atoms and can be substituted, or R 2 is substituted or unsubstituted alkylsulfone having 1 to 6 carbon atoms, substituted or unsubstituted arylsulfone or substituted or unsubstituted aryloxy, or is cyano, nitro or halogen, R 3 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 4 carbon atoms, substituted or unsubstituted phenoxy, or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or R 3 is substituted or unsubstituted alkylsulfone having 1 to 4 carbon atoms, substituted or unsubstituted phenylsulfonic acid ester, cyano, nitro, halogen, substituted or unsubstituted carbalkoxy having 1 to 16 carbon atoms, or --P(O)(OT 1 ) 2 , in which T 1 is alkyl having 1 to 4 carbon atoms, R 4 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 16 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted, or R 4 is --NQ 1 COT 1 , in which Q 1 is hydrogen or alkyl having 1 or 2 carbon atoms and T 1 is substituted or unsubstituted alkyl having 1 to 4 carbon atoms, or R 4 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone hydroxyl, cyano, nitro or halogen, R 5 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms or substituted or unsubstituted carbalkoxy having 2 to 13 carbon atoms, X 1 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 6 carbon atoms or --NL 1 CO--M 1 , in which L 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 4 carbon atoms and M 1 is substituted or unsubstituted alkyl or alkoxy having 1 to 24 carbon atoms, or X 1 is substituted or unsubstituted alkylsulfonylamino having 1 to 25 carbon atoms or hydroxyl, Y 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy having 1 to 12 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or Y 1 is substituted or unsubstituted arylsulfonylamino or --NE 1 COG 1 , in which E 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and G 1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkoxy having 1 to 4 carbon atoms, or Y 1 is --NE 1 P(O)(OG 1 ) 2 , in which E 1 is as defined above and G 1 is alkyl having 1 to 12 carbon atoms, or Y 1 is halogen or hydroxyl, Z 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms or --NA 1 COD 1 , in which A 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and D 1 is substituted or unsubstituted alkyl having 1 to 18 carbon atoms, or Z 1 is substituted or unsubstituted acyl having 2 to 9 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 19 carbon atoms, substituted or unsubstituted alkylsulfonylamino having 1 to 6 carbon atoms, halogen or the atoms which together with Y 1 form a substituted or unsubstituted 5-membered or 6-membered, saturated or unsaturated ring which can contain 1 or 2 hetero-atoms, and W 1 is hydrogen, substituted or unsubstituted alkyl or alkoxy, each having 1 to 4 carbon atoms, or halogen.

Claim 2

Dependent Claim 902 words

A colour-photographic recording material for the silver dye bleach process which contains at least one diffusion-resistant, bleachable and oil-soluble monoazo dye dissolved in a high-boiling organic solvent in at least one silver halide emulsion layer or in a colloid layer adjoining the silver halide emulsion layer, and wherein the dye has the formula ##STR84## in which R 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, substituted or unsubstituted alkoxy having 1 to 16 carbon atoms, substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, substituted or unsubstituted aliphatic acyl having 2 to 5 carbon atoms, substituted or unsubstituted benzoyl, substituted or unsubstituted carbalkoxy having 2 to 20 carbon atoms or --NV 1 COU 1 , in which V 1 is hydrogen or alkyl having 1 to 4 carbon atoms and U 1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, or R 1 is N-alkyl-substituted or N,N-dialkyl-substituted carboxamido or sulfonamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted further, or R 1 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone, substituted or unsubstituted aryloxy or substituted or unsubstituted arylsulfonic acid ester, or is hydroxyl, cyano, nitro or halogen, R 2 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 8 carbon atoms and can be substituted, or R 2 is substituted or unsubstituted alkylsulfone having 1 to 6 carbon atoms, substituted or unsubstituted arylsulfone or substituted or unsubstituted aryloxy, or is cyano, nitro or halogen, R 3 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 4 carbon atoms, substituted or unsubstituted phenoxy, or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or R 3 is substituted or unsubstituted alkylsulfone having 1 to 4 carbon atoms, substituted or unsubstituted phenylsulfonic acid ester, cyano, nitro, halogen, substituted or unsubstituted carbalkoxy having 1 to 16 carbon atoms, or --P(O)(OT 1 ) 2 , in which T 1 is alkyl having 1 to 4 carbon atoms, R 4 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 16 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted, or R 4 is --NQ 1 COT 1 , in which Q 1 is hydrogen or alkyl having 1 or 2 carbon atoms and T 1 is substituted or unsubstituted alkyl having 1 to 4 carbon atoms, or R 4 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone hydroxyl, cyano, nitro or halogen, R 5 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms or substituted or unsubstituted carbalkoxy having 2 to 13 carbon atoms, X 1 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 6 carbon atoms or --NL 1 CO--M 1 , in which L 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 4 carbon atoms and M 1 is substituted or unsubstituted alkyl or alkoxy having 1 to 24 carbon atoms, or X 1 is substituted or unsubstituted alkylsulfonylamino having 1 to 25 carbon atoms or hydroxyl, Y 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy having 1 to 12 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or Y 1 is substituted or unsubstituted arylsulfonylamino or --NE 1 COG 1 , in which E 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and G 1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkoxy having 1 to 4 carbon atoms, or Y 1 is --NE 1 P(O)(OG 1 ) 2 , in which E 1 is as defined above and G 1 is alkyl having 1 to 12 carbon atoms, or Y 1 is halogen or hydroxyl, Z 1 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms or --NA 1 COD 1 , in which A 1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and D 1 is substituted or unsubstituted alkyl having 1 to 18 carbon atoms, or Z 1 is substituted or unsubstituted acyl having 2 to 9 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 19 carbon atoms, substituted or unsubstituted alkylsulfonylamino having 1 to 6 carbon atoms, halogen or the atoms which together with Y 1 form a substituted or unsubstituted 5-membered or 6-membered, saturated or unsaturated ring which can contain 1 or 2 hetero-atoms, and W 1 is hydrogen, substituted or unsubstituted alkyl or alkoxy, each having 1 to 4 carbon atoms, or halogen.

Claim 3

Dependent Claim 763 words

A colour-photographic recording material according to claim 1, which contains a dye of the formula ##STR85## in which R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 16 carbon atoms, substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, substituted or unsubstituted aliphatic acyl having 2 or 3 carbon atoms, substituted or unsubstituted benzoyl, substituted or unsubstituted carbalkoxy having 2 to 16 carbon atoms, or --NV 2 COU 1 , in which V 2 is hydrogen or alkyl having 1 or 2 carbon atoms and U 1 is as defined in claim 1, or R 6 is N-alkyl-substituted or N,N-dialkyl-substituted carboxamido or sulfonamido, in which each alkyl moiety contains 1 to 10 carbon atoms and can be substituted further, or R 6 is substituted or unsubstituted alkylsulfone having 1 to 8 carbon atoms, substituted or unsubstituted phenylsulfone, substituted or unsubstituted phenoxy or substituted or unsubstituted phenylsulfonic acid ester, or is hydroxyl, cyano, nitro or halogen, R 7 is hydrogen, substituted or unsubstituted alkyl having 1 to 8 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 or 3 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety contains 1 to 8 carbon atoms and can be substituted, or R 7 is substituted or unsubstituted alkylsulfone having 1 to 6 carbon atoms, substituted or unsubstituted phenylsulfone or substituted or unsubstituted phenoxy, or is cyano, nitro or halogen, R 8 is hydrogen, alkyl or alkoxy having 1 to 4 carbon atoms, substituted or unsubstituted phenoxy or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 4 carbon atoms, or R 8 is alkylsulfone having 1 to 4 carbon atoms, substituted or unsubstituted phenylsulfonic acid ester, cyano, nitro, halogen, substituted or unsubstituted carbalkoxy having 1 to 16 carbon atoms, or --P(O)(OT 1 ) 2 , in which T 1 is as defined in claim 1, R.sub. 9 is hydrogen, unsubstituted or halogen-substituted alkyl having 1 to 4 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, carbalkoxy having 2 to 16 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 8 carbon atoms and can be substituted, or R 9 is --NQ 1 COT 1 , in which Q 1 and T 1 are as defined in claim 1, or R 9 is alkylsulfone having 1 to 6 carbon atoms, phenylsulfone, hydroxyl, cyano, nitro or halogen, R 10 is hydrogen, alkyl having 1 to 4 carbon atoms or carbalkoxy having 2 to 13 carbon atoms, X 2 is hydrogen, alkyl or alkoxy, each having 1 to 6 carbon atoms, or --NL 2 COM 2 , in which L 2 is hydrogen or alkyl having 1 to 4 carbon atoms and M 2 is substituted or unsubstituted alkyl or alkoxy having 1 to 18 carbon atoms, or X 2 is alkylsulfonylamino having 1 to 18 carbon atoms, or hydroxyl, Y 2 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 12 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms, or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety contains 1 to 6 carbon atoms and can be substituted, or Y 2 is substituted or unsubstituted phenylsulfonylamino or --NE 2 COG 2 , in which E 2 is hydrogen or unsubstituted or cyano-substituted alkyl having 1 to 8 carbon atoms and G 2 is alkyl having 1 to 8 carbon atoms or substituted or unsubstituted alkoxy having 1 to 4 carbon atoms, or Y 2 is --NHP(O)(OG 2 ) 2 , in which G 2 is alkyl having 1 to 6 carbon atoms, or Y 2 is halogen or hydroxyl, Z 2 is hydrogen, alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms or --NA 2 COD 2 , in which A 2 is hydrogen or alkyl having 1 to 8 carbon atoms and D 2 is alkyl having 1 to 18 carbon atoms, or Z 2 is acyl having 2 to 7 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 19 carbon atoms, alkylsulfonylamino having 1 to 6 carbon atoms, halogen or the atoms which together with Y 2 form an unsubstituted or methyl-substituted 6-membered, saturated or unsaturated ring which can contain one or two hetero-atoms and W 2 is hydrogen, alkyl or alkoxy each having 1 to 4 carbon atoms, or halogen.

Claim 4

Dependent Claim 922 words

A colour-photographic recording material as claimed in claim 2, which contains a dye of the formula ##STR86## in which R 11 is hydrogen, alkyl having 1 to 12 carbon atoms which is substituted by alkoxy having 1 to 4 carbon atoms or by carbalkoxy having 2 to 12 carbon atoms or is unsubstituted, alkoxy having 1 to 16 carbon atoms, a radical of the formula --O--(CH.sub.2).sub.m.sbsb.1 --OC.sub.2 H.sub.4 ].sub.n O--CH.sub.2).sub.m CH.sub.3, in which m 1 is an integer from 2 to 16, n is 1 or 2 and m is an integer from 0 to 3, alkenyl having 2 to 4 carbon atoms, which is substituted by cyano and/or by carbalkoxy having 2 to 9 carbon atoms or is unsubstituted, aliphatic acyl having 2 or 3 carbon atoms, benzoyl which is substituted by chlorine, --CO 2 B 1 , --SO 2 B 1 or --COB 1 , in which B 1 is alkyl having 1 to 8 carbon atoms, or is unsubstituted, or R 11 is carbalkoxy having 2 to 16 carbon atoms, a radical of the formula ##STR87## in which m 1 and n are as defined above, or --NV 3 COU 2 , in which V 3 is hydrogen and U 2 is unsubstituted or methoxy- or hydroxyl-substituted alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 4 carbon atoms, or R 11 is carboxamido or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 10 carbon atoms and can be substituted by methoxy, hydroxyl or amino, or R 11 is alkylsulfone having 1 to 8 carbon atoms, unsubstituted or substituted phenylsulfone, unsubstituted or substituted phenoxy, unsubstituted or substituted phenylsulfonic acid ester, hydroxyl, cyano, nitro or halogen, R 12 is hydrogen, unsubstituted or halogen-substituted alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, carbalkoxy having 2 or 3 carbon atoms, a radical of the formula ##STR88## or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 8 carbon atoms and can be substituted by methoxy, or R 12 is alkylsulfone having 1 to 6 carbon atoms, phenylsulfone or phenoxy which is unsubstituted or substituted by alkyl having 1 to 8 carbon atoms, or is cyano, nitro or halogen, R 13 is hydrogen, unsubstituted or fluorine-substituted alkyl having 1 or 2 carbon atoms, unsubstituted or methoxy-substituted alkoxy having 1 to 6 carbon atoms, carbalkoxy having 2 to 13 carbon atoms or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 4 carbon atoms and can be methoxy-substituted, or R 13 is --NQ 2 COT 2 , in which Q 2 is hydrogen and T 2 is alkyl having 1 to 4 carbon atoms, or R 13 is methylsulfone, phenylsulfone, hydroxyl, cyano, nitro or halogen X 3 is hydrogen, alkyl or alkoxy each having 1 to 4 carbon atoms, or --NL 3 COM 3 , in which L 3 is hydrogen or methyl and M 3 is alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by halogen, by carbalkoxy having 2 to 5 carbon atoms, by substituted or unsubstituted phenyl or phenoxy or by alkoxy having 1 to 5 carbon atoms, or X 3 is alkylsulfonylamino having 1 to 12 carbon atoms or hydroxyl, Y 3 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 12 carbon atoms, unsubstituted or --OC 2 H 4 --OCH 3 -substituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted by methoxy, by carbalkoxy having 2 to 5 carbon atoms, by acetoxy, by hydroxyl, by nitro, by cyano, by phenyl or by tosyl, or Y 3 is pyrrolidinyl, piperidinyl, morpholinyl or phenylsulfonylamino which is unsubstituted or substituted by alkyl having 1 to 4 carbon atoms, or Y 3 is --NE 3 COG 3 , in which E 3 is hydrogen or unsubstituted or cyano-substituted alkyl having 1 to 4 carbon atoms and G 3 is alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 4 carbon atoms or a radical of the formula --O--(CH 2 ) k --OC 2 H 4 ) n OCH 3 in which k is an integer from 1 to 5 and n is as defined above, or Y 3 is ##STR89## in which G 3 is alkyl having 1 to 4 carbon atoms, or Y 3 is halogen or hydroxyl, Z 3 is hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, a radical of the formula --O--(CH 2 ) k .sbsb.1 --O--(CH 2 ) m --CH 3 in which k 1 is an integer from 2 to 6 and m is as defined above, or Z 3 is --NA 3 COD 3 , in which A 3 is hydrogen or alkyl having 1 to 4 carbon atoms and D 3 is alkyl having 1 to 12 carbon atoms, or Z 3 is acyl having 2 to 5 carbon atoms, carbalkoxy having 2 to 5 carbon atoms, a radical of the formula ##STR90## in which k and n are as defined above, methylsulfonylamino, halogen or the atoms which together with Y 3 form an unsubstituted or methyl-substituted 6-membered saturated or unsaturated ring which contains nitrogen or nitrogen and oxygen, W 3 is hydrogen, alkyl or alkoxy each having 1 or 2 carbon atoms, or halogen, and R 8 and R 10 are as defined in claim 2.

Claim 5

Dependent Claim 535 words

A colour-photographic recording material according to claim 3, which contains a dye of the formula ##STR91## in which R 14 is hydrogen, alkyl which has 1 to 12 carbon atoms and is unsubstituted or substituted by alkoxy having 1 to 4 carbon atoms or by carbalkoxy having 2 to 7 carbon atoms, alkoxy having 1 to 12 carbon atoms, a radical of the formula --O(CH 2 ) m .sbsb.2 --OC 2 H 4 ) n O(CH 2 ) m CH 3 in which m 2 is an integer from 2 to B 12 and n and m are as defined in claim 3, or alkenyl which has 2 to 4 carbon atoms and is unsubstituted or substituted by cyano and/or by carbalkoxy having 2 to 7 carbon atoms, or R 14 is aliphatic acyl having 2 or 3 carbon atoms, or benzoyl which is unsubstituted or substituted by chlorine, --CO 2 B 2 , --SO 2 B 2 or --COB 2 , in which B 2 is alkyl having 1 to 4 carbon atoms, or R 14 is carbalkoxy having 2 to 9 carbon atoms, a radical of the formula ##STR92## in which m 3 is an integer from 2 to 8 and n is as defined above, or --NHCOU 3 , in which U 3 is alkyl having 1 to 8 carbon atoms or alkenyl having 2 or 3 carbon atoms, or R 14 is carboxamido or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 5 carbon atoms and can be substituted by methoxy, hydroxyl or amino, or R 14 is alkylsulfone having 1 to 6 carbon atoms, unsubstituted or C 1-5 -alkyl-substituted or hydroxyl-substituted phenylsulfone or phenylsulfonic acid ester, hydroxyl, cyano, nitro or halogen, R 15 is hydrogen, unsubstituted or fluorine-substituted alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, carbalkoxy having 2 or 3 carbon atoms, a radical of the formula ##STR93## or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 4 carbon atoms and can be methoxy-substituted, or R 15 is alkylsulfone having 1 to 4 carbon atoms or R 15 is cyano, nitro or halogen, R 16 is hydrogen, methyl, methoxy, or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be methoxy-substituted, or R 16 is alkylsulfone having 1 to 4 carbon atoms, phenylsulfonic acid ester, cyano, nitro, halogen, unsubstituted or methoxy-substituted carbalkoxy having 1 to 12 carbon atoms or --P(O)(OT 1 ) 2 , in which T 1 is as defined in claim 2, R 17 is hydrogen, methyl, trifluoromethyl, alkoxy having 1 to 4 carbon atoms, carbalkoxy having 2 to 9 carbon atoms or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be methoxy-substituted, or R 17 is --NHCOT 2 , in which T 2 is as defined in claim 3, or R 17 is methylsulfone, phenylsulfone, hydroxyl, cyano, nitro or halogen, R 18 is hydrogen, methyl or carbalkoxy having 2 to 7 carbon atoms and X 3 , Y 3 , Z 3 and W 3 are as defined in claim 3.

Claim 6

Dependent Claim 455 words

A colour-photographic recording material according to claim 4, which contains a dye of the formula ##STR94## in which X 4 is hydrogen, alkyl having 1 to 4 carbon atoms, methoxy or --NL 4 COM 4 , in which L 4 is hydrogen or methyl and M 4 is alkyl having 1 to 13 carbon atoms, or alkoxy having 1 to 4 carbon atoms, which can both be substituted by phenyl or phenoxy or by (C m .sbsb.3 H 2m .sbsb.3 +1 --C 6 H 4 -- or (C m .sbsb.3 H 2m .sbsb.3 +1 --C 6 H 4 --O-- or by fluorine, chlorine, alkoxy having 1 to 5 carbon atoms or by carbalkoxy having 2 or 3 carbon atoms, m 3 being as defined in claim 4, or X 4 is alkylsulfonylamino having 1 to 6 carbon atoms, or hydroxyl, Y 4 is hydrogen, alkyl having 1 or 2 carbon atoms, alkoxy having 1 to 8 carbon atoms, unsubstituted or --OC 2 H 4 --OCH 3 -- substituted carbalkoxy having 2 or 3 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted by methoxy, carbalkoxy having 2 to 5 carbon atoms, acetoxy, hydroxyl, nitro, cyano or phenyl, or Y 4 is pyrrolidinyl, piperidinyl or phenylsulfonamino which can be substituted by alkyl having 1 to 4 carbon atoms, or Y 4 is --NE 3 COG 4 , in which E 3 is as defined in claim 3, and G 4 is alkyl having 1 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, or a radical of the formula --O--CH 2 --CH 2 --OC 2 H 4 OC 2 H 5 or --O--CH 2 --CH 2 --OC 2 4 --OCH 3 , or Y 4 is ##STR95## in which G 3 is as defined in claim 3, or Y 4 is halogen or hydroxyl, Z 4 is hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, --O(CH 2 ) k --O(CH 2 ) m --CH 3 , in which k and m are as defined in claim 3, or --NA 4 COD 4 , in which A 4 is hydrogen or methyl and D 4 is alkyl having 1 to 8 carbon atoms, or Z 4 is acetyl, carbalkoxy having 2 to 5 carbon atoms, a radical of the formula ##STR96## in which k is as defined in claim 3, methylsulfonylamino, halogen or the atoms which together with Y 4 form ring systems such as ##STR97## W 4 is hydrogen, methyl, methoxy or halogen and R 14 , R 15 , R 16 , R 17 and R 18 are as defined in claim 4.

Claim 7

Dependent Claim 617 words

A colour-photographic recording material according to claim 5, which contains a dye of the formula ##STR98## in which R 19 is hydrogen, alkyl having 1 to 6 carbon atoms which can be substituted by alkoxy having 1 to 4 carbon atoms or by carbalkoxy having 2 to 7 carbon atoms, alkoxy having 1 to 8 carbon atoms, a radical of the formula --O--CH 2 ) m .sbsb.3 OC 2 H 4 --OCH 3 or --O--CH 2 ) m .sbsb.3 OC 2 H 4 --OC 2 H 5 , in which m 3 is as defined in claim 4, vinyl which can be substituted by cyano and/or by carbalkoxy having 2 to 7 carbon atoms, acetyl, benzoyl which can be substituted in the para-position by chlorine, --CO 2 B 2 , --SO 2 B 2 -- or --COB 2 , in which B 2 is as defined in claim 4, carbalkoxy having 2 to 9 carbon atoms, a radical of the formula ##STR99## in which m 3 is as defined in claim 4, or --NHCOU 4 , in which U 4 is alkyl having 1 to 4 carbon atoms or alkenyl having 2 or 3 carbon atoms, or R 19 is carboxamido or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 5 carbon atoms and can be substituted by methoxy, hydroxyl or amino, or R 19 is alkyl-sulfone having 1 to 6 carbon atoms or phenylsulfone or phenylsulfonic acid ester, which two radicals can be substituted in the para-position by alkyl having 1 to 5 carbon atoms or hydroxyl, or R 19 is hydroxyl, cyano, nitro, chlorine or bromine, R 20 is hydrogen, methyl, trifluoromethyl, methoxy, ethoxy, carbalkoxy having 2 or 3 carbon atoms, a radical of the formula ##STR100## or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 4 carbon atoms and can be substituted by methoxy, or R 20 is alkylsulfone having 1 to 4 carbon atoms, phenylsulfone or R 20 is cyano, nitro, chlorine or bromine, R 21 is hydrogen, methyl, methoxy, phenoxy or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 2 carbon atoms, or R 21 is alkylsulfone having 1 to 4 carbon atoms, cyano, nitro, bromine, chlorine or unsubstituted or methoxy-substituted carbalkoxy having 2 to 7 carbon atoms, or R 21 is --P(O)(OC 2 H 5 ) 2 , R 22 is hydrogen, methyl, trifluoromethyl, unsubstituted or methoxy-substituted alkoxy having 1 to 2 carbon atoms, carbalkoxy having 2 to 9 carbon atoms or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be substituted by methoxy, or R 22 is --NHCOT 2 , in which T 2 is as defined in claim 4, or R 22 is methylsulfone, phenylsulfone, hydroxyl, cyano, chlorine or bromine, R 23 is hydrogen, methyl or carbalkoxy having 2 or 3 carbon atoms, X 5 is hydrogen, alkyl having 1 to 4 carbon atoms, methoxy or --NL 5 -COM 5 , in which L 5 is hydrogen and M 5 is alkyl having 1 to 8 carbon atoms, or alkoxy having 1 or 2 carbon atoms, which radicals can be substituted by fluorine, chlorine, alkoxy having 1 to 5 carbon atoms, carbalkoxy having 2 or 3 carbon atoms, phenyl, para-(C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 --, phenoxy, or para-C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 --O--, m 3 being as defined in claim 4, or X 5 is alkylsulfonylamino having 1 to 6 carbon atoms, or hydroxyl, W 5 is hydrogen, methyl, methoxy or chlorine and Y 4 and Z 4 are as defined in claim 5.

Claim 8

Dependent Claim 546 words

A colour-photographic recording material as claimed in claim 6, which contains a dye of the formula ##STR101## in which R 24 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by carbalkoxy having 2 to 7 carbon atoms, or R 24 is alkoxy having 1 to 4 carbon atoms, a radical of the formula --O--(CH 2 ) k --OC 2 H 4 --OCH 3 or --O--(CH 2 ) k --OC 2 H 4 --OC 2 H 5 , in which k is as defined in claim 3, carbalkoxy having 2 to 9 carbon atoms, a radical of the formula ##STR102## in which m 3 is as defined in claim 4, --NHCOU 4 , in which U 4 is as defined in claim 6, carboxamido or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1, 2 or 3 carbon atoms and can be substituted by methoxy, or R 24 is alkylsulfone having 1 to 6 carbon atoms or is phenylsulfone or phenylsulfonic acid ester, each of which two radicals can be substituted in the para-position by alkyl having 1 to 5 carbon atoms or hydroxyl, or R 24 is hydroxyl, nitro, chlorine or bromine, R 25 is hydrogen, methyl, methoxy, ethoxy, carbalkoxy having 2 or 3 carbon atoms, a radical of the formula ##STR103## or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be substituted by methoxy, or R 25 is alkylsulfone having 1 to 4 carbon atoms or R 25 is cyano, nitro, chlorine or bromine, R 26 is hydrogen, cyano, chlorine or bromine, R 27 is hydrogen or alkoxy having 1 or 2 carbon atoms, or R 27 is carbalkoxy having 2 to 9 carbon atoms, --NHCOT 2 , in which T 2 is as defined in claim 6, hydroxyl or chlorine, R 28 is hydrogen or carbalkoxy having 2 or 3 carbon atoms, X 6 is hydrogen, alkyl having 1 to 4 carbon atoms, methoxy or --NHCOM 6 , in which M 6 is alkyl having 1 to 4 carbon atoms which is optionally substituted by alkoxy having 1 to 5 carbon atoms, by phenoxy or para-(C k H 2k+1 )--C 6 H 4 --O--, k being as defined in claim 3, or X 6 is hydroxyl, Y 5 is hydrogen, alkoxy having 1 to 4 carbon atoms, unsubstituted or --OC 2 H 4 --OCH 3 -- substituted carbalkoxy having 2 or 3 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 4 carbon atoms and can be substituted by methoxy, carbalkoxy having 2 or 3 carbon atoms, acetoxy, hydroxyl, cyano or phenyl, or Y 5 is --NE 3 COG 4 , in which E 3 and G 4 are as defined in claim 5, or Y 5 is hydroxyl, Z 5 is hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 4 carbon atoms, acetyl, carbalkoxy having 2 to 5 carbon atoms, a radical of the formula ##STR104## in which k is as defined in claim 3, --NA 4 COD 4 , in which A 4 and D 4 are as defined in claim 5, or chlorine, and W 5 is as defined in claim 6.

Claim 9

Dependent Claim 168 words

A colour-photographic recording material according to claim 7, which contains a dye of the formula ##STR105## in which R 29 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, carbalkoxy having 2 to 9 carbon atoms or a radical of the formula ##STR106## in which m 3 is as defined in claim 7, R 30 is hydrogen, methyl, methoxy, cyano, chlorine or bromine, R 31 is hydrogen or bromine, R 32 is hydrogen or chlorine, R 33 is hydrogen or carbomethoxy, X 7 is ##STR107## in which M 7 is alkyl having 1 to 4 carbon atoms, or X 7 is hydroxyl, Y 6 is hydrogen, N-alkyl-substituted amino, in which the alkyl moiety has 1 or 2 carbon atoms and can be cyano-substituted, or --NE 3 COG 4 , in which E 3 and G 4 are as defined in claim 5, Z 6 is hydrogen or alkoxy having 1 to 4 carbon atoms and W 6 is hydrogen or methyl.

Claim 10

Dependent Claim 18 words

A colour-photographic recording material according to claim 8, which contains a dye of one of the formulae ##STR108##

Claim 11

Dependent Claim 437 words

A colour-photographic recording material according to claim 6, which contains a dye of the formula ##STR109## in which R 34 is hydrogen or alkyl having 1 or 2 carbon atoms, which can be substituted by carbalkoxy having 2 or 3 carbon atoms, or is carbalkoxy having 2 or 3 carbon atoms, a radical of the formula ##STR110## or vinyl which can be substituted by cyano and/or carbalkoxy having 2 to 5 carbon atoms, or R 34 is N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 3 carbon atoms and can be methoxy-substituted, alkylsulfone having 1 to 6 carbon atoms, phenylsulfonic acid ester, para-(C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 --O--SO 2 --, in which m 3 is as defined in claim 4, cyano, nitro, chlorine or bromine, R 35 is hydrogen, trifluoromethyl, carbalkoxy having 2 or 3 carbon atoms, alkylsulfone having 1 to 4 carbon atoms, N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 4 carbon atoms and can be methoxy-substituted, cyano, nitro, chlorine or bromine, R 36 is hydrogen, methylsulfone, N,N-diethylsulfonamide, cyano, nitro, chlorine or bromine, R 37 is hydrogen, methyl, carbalkoxy having 2 to 7 carbon atoms, N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be methoxy-substituted, cyano or chlorine, R 38 is hydrogen or methyl, X 8 is hydrogen, methyl or --NHCOM 7 , in which M 7 is alkyl having 1 to 8 carbon atoms which is unsubstituted or substituted by carbalkoxy having 2 or 3 carbon atoms, fluorine, chlorine, phenyl, phenoxy, para-(C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 -- or para-(C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 O--, or X 8 is alkylsulfonylamino having 1 to 6 carbon atoms, or hydroxyl, Y 7 is alkyl having 1 or 2 carbon atoms, alkoxy having 1 to 8 carbon atoms, unsubstituted or --OC 2 H 4 --OCH 3 -substituted carbalkoxy having 2 or 3 carbon atoms, or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 4 carbon atoms and can be substituted by methoxy, carbomethoxy, acetoxy, cyano, hydroxyl or phenyl, or Y 7 is --NHCOG 5 , in which G 5 is alkyl having 1 to 4 carbon atoms, and Z 7 is hydrogen, alkoxy having 1 to 2 carbon atoms, a radical of the formula --OCH 2 CH 2 --O(CH 2 ) m --CH 3 , in which m is as defined in claim 5, --NHCOD 4 , in which D 4 is as defined in claim 5, or chlorine,

Claim 12

Dependent Claim 224 words

A colour-photographic recording material according to claim 10, which contains a dye of the formula ##STR111## in which R 39 is hydrogen or alkyl having 1 to 2 carbon atoms, which can be substituted by carbalkoxy having 2 or 3 carbon atoms, or R 39 is carbalkoxy having 2 or 3 carbon atoms, alkylsulfone having 1 to 6 carbon atoms, N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 3 carbon atoms and can be methoxy-substituted, cyano, nitro, chlorine or bromine, R 40 is hydrogen, alkylsulfone having 1 to 4 carbon atoms, N,N-dimethylsulfonamide or N,N-diethylsulfonamide, cyano or nitro, R 41 is hydrogen, methylsulfone, cyano or nitro, R 42 is hydrogen or cyano, X 9 is methyl or ##STR112## in which M 8 is alkyl having 1 to 4 carbon atoms, or X 9 is hydroxyl, Y 8 is alkoxy having 1 to 8 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 4 carbon atoms and can be substituted by methoxy, acetoxy or cyano, and Z 8 is hydrogen, alkoxy having 1 or 2 carbon atoms, a radical of the formula --OCH 2 CH 2 --O(CH 2 ) m --CH 3 , in which m is as defined in claim 3, or --NHCOD 4 , in which D 4 is as defined in claim 10.

Claim 13

Dependent Claim 18 words

A colour-photographic recording material according to claim 11, which contains a dye of one of the formulae ##STR113##

Claim 14

Dependent Claim 223 words

A colour-photographic recording material according to claim 6, which contains a dye of the formula ##STR114## in which R 43 is vinyl which can be substituted by cyano and/or carbalkoxy having 2 to 7 carbon atoms, or R 43 is carbalkoxy having 2 or 3 carbon atoms, N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 to 5 carbon atoms and can be methoxy-, amino- or hydroxyl-substituted, alkylsulfone having 1 to 6 carbon atoms, phenylsulfonic acid ester, para-(C m .sbsb.3 H 2m .sbsb.3 +1 )--C 6 H 4 --O--SO 2 --, in which m 3 is as defined in claim 10, cyano or nitro, R 44 is N,N-dimethylsulfonamido or N,N-diethylsulfonamido, cyano, nitro, chlorine, bromine, methylsulfone or trifluoromethyl, R 46 is hydrogen or carbalkoxy having 2 to 6 carbon atoms, X 10 is methyl ##STR115## in which M 5 is as defined in claim 6, or alkylsulfonamide having 1 to 6 carbon atoms, Y 9 is unsubstituted or --OC 2 H 4 -OCH 3 -substituted carbalkoxy having 2 or 3 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 4 carbon atoms and can be substituted by methoxy, acetoxy, cyano, hydroxyl or phenyl, and Z 9 is hydrogen, methoxy, --OCH 2 -CH 2 -OC 2 H 5 , or --OCH 2 CH 2 -OCH 3 .

Claim 15

Dependent Claim 90 words

A colour-photographic recording material according to claim 13, which contains a dye of the formula ##STR116## in which R 47 is vinyl which can be substituted by cyano and/or carbalkoxy having 2 or 3 carbon atoms, or R 47 is N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido, in which each alkyl moiety has 1 or 2 carbon atoms and can be methoxy-substituted, cyano or nitro, R 48 is cyano, trifluoromethyl or nitro, X 11 is ##STR117## in which M 8 is as defined in claim 11, and Y 10 is dimethylamino or diethylamino.

Claim 16

Dependent Claim 18 words

A colour-photograhic recording material according to claim 14, which contains a dye of one of the formulae ##STR118##

Claim 17

Dependent Claim 61 words

A process for the preparation of a colour-photographic recording material for the silver dye bleach process, which comprises incorporating at least one non-diffusible, bleachable and oil-soluble monoazo dye of the formula (1) in claim 1 dissolved in a high-boiling organic solvent into at least one silver halide emulsion layer or into a colloid layer adjacent to the silver halide emulsion layer.

Claim 18

Dependent Claim 13 words

A photographic image produced with the colour-photographic recording material according to claim 1.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1986-04-11	1986-10-11	1987-04-12	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1990-04-11	1990-10-11	1991-04-12	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1994-04-11	1994-10-11	1995-04-12	$7700.00	Window Closed / Lapsed

Color-photographic recording material for the silver dye bleach process

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