Color photographic material

A process for preventing the migration of oxidised developer in a colour photographic material from a light sensitive silver halide emulsion layer in which it has been formed into another silver halide emulsion layer containing colour couplers comprising the steps of:

• incorporating a compound of the formula I
• wherein, if n=1,
• R1 is a cyclic residue selected from naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each of which is unsubstituted or substituted by C1–C4alkyl, C1–C4alkoxy, C1–C4alkylthio, hydroxy, halogen, amino, C1–C4alkylamino, phenylamino or di(C1–C4-alkyl)amino;
• or R1 is a radical of formula II
• and, if n=2,
• R1 is unsubstituted or C1–C4alkyl- or hydroxy-substituted phenylene or naphthylene;
• or —R12—X—R13—;
• R2, R3, R4 and R5 are each independently of one another hydrogen;
• chloro;
• hydroxy;
• C1–C25-alkyl;
• C7–C9phenylalkyl;
• unsubstituted or C1–C4alkyl-substituted phenyl;
• unsubstituted or C1–C4alkyl-substituted C5–C8cycloalkyl;
• C1–C18alkoxy;
• C1–C18alkylthio;
• C1–C4alkylamino;
• di(C1–C4-alkyl)amino;
• C1–C25alkanoyloxy;
• C1–C25alkanoylamino;
• C3–C25alkenoyloxy;
• C3–C25alkanoyloxy which is interrupted by oxygen, sulphur or
• C6–C9cycloalkylcarbonoyloxy;
• benzoyloxy or C1–C12alkyl-substituted benzoyloxy;
• or R2 and R3, or R3 and R4, or R4 and R5, together with the linking carbon atoms, form a benzene ring;
• or R4 is —CmH2m—COR15, —O—(CvH2v)—COR′15, —O—(CH2)q—OR32, —OCH2—CH(OH)—CH2—R′15, —OCH2—CH(OH)—CH2—OR32, or —(CH2)qOH;
• or, if R3, R5 and R6 are hydrogen, R4 is additionally a radical of formula III
• wherein R1 is as defined above for n=1;
• R6 is hydrogen or, when R4 is hydroxy, R6 can also be C1–C25alkyl or C3–C25alkenyl;
• R7 and R8 are each independently of one another hydrogen;
• halogen;
• C1–C25alkyl;
• C2–C25alkyl which is interrupted by oxygen, sulphur or
• C1–C25alkylthio;
• C3–C25-alkenyl;
• C3–C25alkenyloxy;
• C3–C25alkynyl;
• C3–C25alkynyloxy;
• C7–C9phenylalkyl;
• C7–C9phenylalkoxy;
• unsubstituted or C1–C4alkyl-substituted phenyl;
• unsubstituted or C1–C4alkyl-substituted phenoxy;
• unsubstituted or C1–C4alkyl-substituted C5–C8cycloalkyl;
• unsubstituted or C1–C4alkyl-substituted C5–C8cycloalkoxy;
• C1–C4alkylamino;
• di(C1–C4alkyl)amino;
• C1–C25alkanoyl;
• C3–C25alkanoyl which is interrupted by oxygen, sulphur or
• C1–C25alkanoylamino;
• C3–C25alkenoyl;
• C3–C25alkenoyl which is interrupted by oxygen, sulphur or
• C3–C25alkenoyloxy;
• C3–C25alkenoyloxy which is interrupted by oxygen, sulphur or
• C6–C9cycloalkylcarbonyl;
• C6–C9cycloalkylcarbonyloxy;
• benzoyl or C1–C12alkyl-substituted benzoyl;
• benzoyloxy or C1–C12alkyl-substituted benzoyloxy;
• or
• R8, R10 and R11 are each independently of one another hydrogen;
• halogen;
• hydroxy;
• C1–C25alkyl;
• C2–C25alkyl which is interrupted by oxygen, sulphur or
• C1–C25alkoxy;
• C2–C25alkoxy which is interrupted by oxygen, sulphur or
• C1–C25alkylthio;
• C3–C25-alkenyl;
• C3–C25alkenyloxy;
• C3–C25alkynyl;
• C3–C25alkynyloxy;
• C7–C9phenylalkyl;
• C7–C9phenylalkoxy;
• unsubstituted or C1–C4alkyl-substituted phenyl;
• unsubstituted or C1–C4alkyl-substituted phenoxy;
• unsubstituted or C1–C4alkyl-substituted C5–C8cycloalkyl;
• unsubstituted or C1–C4alkyl-substituted C5–C8cycloalkoxy;
• C1–C4alkylamino;
• di(C1–C4alkyl)amino;
• C1–C25alkanoyl;
• C3–C25alkanoyl which is interrupted by oxygen, sulphur or
• C1–C25alkanoyloxy;
• C3–C25alkanoyloxy which is interrupted by oxygen, sulphur or
• C1–C25alkanoylamino;
• C3–C25alkenoyl;
• C3–C25alkenoyl which is interrupted by oxygen, sulphur or
• C3–C25alkenoyloxy;
• C3–C25alkenoyloxy which is interrupted by oxygen, sulphur or
• C6–C9cycloalkylcarbonyl;
• C6–C9cycloalkylcarbonyloxy;
• benzoyl or C1C12alkyl-substituted benzoyl;
• benzoyloxy or C1–C12alkyl-substituted benzoyloxy;
• or
• or, in formula II, R7 and R8, or R8 and R11, together with the linking carbon atoms, form a benzene ring;
• R12 and R13 are each independently of the other unsubstituted or C1–C4alkyl-substituted phenylene or naphthylene;
• R14 is hydrogen or C1–C8alkyl;
• R15 and R′15 independently are hydroxy;
• [
• —O
• -
• ⁢
• 1
• r
• ⁢
• M
• r
• +
• ]
• ;
• C1–C20alkoxy;
• C3–C20alkoxy interrupted by O and/or substituted by a radical selected from OH, phenoxy, C7–C15alkylphenoxy, C7–C15alkoxyphenoxy;
• or are C5–C12cycloalkoxy;
• C7–C17phenylalkoxy;
• phenoxy;
• or a group of the formula IIIa or IIIb
• R16 and R17 are each independently of the other hydrogen, CF3, C1–C12alkyl or phenyl, or R16 and R17, together with the linking carbon atom, are a C5–C8cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C1–C4alkyl;
• R18 and R19 are each independently of the other hydrogen, C1–C4alkyl or phenyl;
• R20 is hydrogen or C1–C4alkyl;
• R21 is hydrogen;
• unsubstituted or C1–C4alkyl-substituted phenyl;
• C1–C25alkyl;
• C2–C25alkyl which is interrupted by oxygen, sulphur or
• C7–C9phenylalkyl which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1–C4alkyl;
• C7–C25phenylalkyl which is interrupted by oxygen, sulphur or
• and which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C1–C4alkyl;
• or R20 and R21, together with the linking carbon atoms, form a C5–C12cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C1–C4alkyl;
• R22 is hydrogen or C1–C4alkyl;
• R23 is hydrogen;
• C1–C25alkanoyl;
• C3–C25alkenoyl;
• C3–C25alkanoyl which is interrupted by oxygen, sulphur or
• C2–C25alkanoyl which is substituted by a di(C1–C6alkyl)phosphonate group;
• C6–C9cycloalkylcarbonyl;
• thenoyl;
• furoyl;
• benzoyl or C1–C12alkyl-substituted benzoyl;
• or
• R24 and R25 are each independently of the other hydrogen or C1–C18alkyl;
• R26 is hydrogen or C1–C8alkyl;
• R27 is a direct bond;
• C1–C18alkylene;
• C2–C18alkylene which is interrupted by oxygen, sulphur or
• C2–C18alkenylene;
• C2–C20alkylidene;
• C7–C20phenylalkylidene;
• C5–C8cycloalkylene;
• C7–C8bicycloalkylene;
• unsubstitued or C1–C4alkyl-substituted phenylene;
• or
• R28 is hydroxy,
• [
• —O
• -
• ⁢
• 1
• r
• ⁢
• M
• r
• +
• ]
• ,
• C1–C18alkoxy or
• R29 is oxygen or —NH—;
• R30 is C1–C18alkyl or phenyl;
• R31 is hydrogen or C1–C18alkyl;
• R32 is C1–C18alkanoyl;
• C1–C8alkanoyl substituted by phenyl or C7–C15alkylphenyl;
• C3–C18alkenoyl;
• cyclohexylcarbonyl;
• or naphthylcarbonyl;
• L is a linking group of valency (k+1) and is as a divalent group
• —O—;
• Q—C2–C12alkylene-Q;
• —O—CH2—CH(OH)—CH2—O—;
• —Q—C2–C12alkylene-Q—CO—CvH2v—O—;
• —O—C2–C12alkylene-O—CH2—CH(OH)—CH2—O—;
• Q-phenylene-Q or
• Q-phenylene-D-phenylene-Q with D being C1–C4alkylene, O, S, SO or SO2;
• L as a trivalent group is Q-capped C3–C12alkanetriyl, a trivalent residue of a hexose or a hexitol, or a group (—O—CH2)3C—CH2OH;
• —Q—CaH2a—N(CbH2b—Q—)—CcH2c—Q—;
• —Q—C3–C12alkanetriyl(—Q—CO—CvH2v—O—)2;
• —O—C3–C12alkanetriyl(—O—CH2—CH(OH)—CH2—O—)2;
• and
• L as a tetravalent group is a tetravalent residue of a hexose or a hexitol;
• —Q—C4–C12alkanetetryl(—Q—CO—CvH2v—O—)3;
• —O—C4–C12alkanetetryl(—O—CH2—CH(OH)—CH2—O—)3;
• Q-capped C4–C12alkanetetryl;
• a group
• or a group
• M is an r-valent metal cation;
• Q is oxygen or —NH—;
• X is a direct bond, oxygen, sulphur or —NR31—;
• Z is a linking group of valency (k+1) and is as a divalent group C2–C12alkylene;
• Q-interrupted C4–C12alkylene;
• phenylene or phenylene-D-phenylene with D being C1–C4alkylene, O, S, SO or SO2;
• Z as a trivalent group is C3–C12alkanetriyl, a trivalent residue of a hexose or a hexitol, a group (—CH2)3C—CH2OH, or a group —CaH2a—N(CbH2b—)—CcH2c—;
• and
• Z as a tetravalent group is a tetravalent, carbon-ended residue of a hexose or a hexitol, C4–C12alkanetetryl, a group
• or a group
• a, b, c and k independently are 1, 2 or 3;
• m is 0 or a number from the range 1–12;
• n is 1 or 2;
• q is 1, 2, 3, 4, 5 or 6;
• r is 1, 2 or 3;
• and
• s is 0, 1 or 2;
• v is 1, 2, 3, 4, 5, 6, 7 or 8;
• provided that, when R7 is hydroxy, alkanoyloxy or alkanoyloxy interrupted by O, S or N(R14) and R9 is hydrogen, R10 is not identical with R4;
• and when R9 is hydroxy, alkanoyloxy or alkanoyloxy interrupted by O, S or N(R14) and R7 is hydrogen, R8 is not identical with R4, into an interlayer between the light sensitive silver halide emulsion layers thus scavenging the oxidized form of developer when migrating from the light sensitive silver halide emulsion layer in which it has been formed to the interlayer.