Color-photographic recording material
AssigneeCiba-Geigy Corporation
InventorDavid G. Leppard
Life of this patent
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Abstract
A color-photographic recording material which, in at least one light-sensitive silver halide emulsion layer, an interlayer and/or a protective layer, contains at least one polyalkylpiperidine compound of the formula I ##STR1## as a light stabilizer. Color images obtained by imagewise exposure and development of this color-photographic recording material display good stability to the action of visible and ultra-violet light. With respect to the definitions of the substituents and symbols in formula I, reference is made to the specification.
Claims9
A colour-photographic recording material which, in at least one light-sensitive silver halide emulsion layer, an interlayer and/or a protective layer, contains a light stabilising amount of at least one polyalkylpiperidine compound as a light stabiliser, wherein the polyalkylpiperidine compound is of the formula I ##STR61## in which R.sub.1 and R.sub.3 independently of one another are hydrogen or methyl, R.sub.2 is hydroxyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.3 -C.sub.4 -alkynyl, 2-hydroxyethyl, C.sub.2 -C.sub.11 -alkoxyalkyl, C.sub.7 -C.sub.14 -aralkyl or a group of the formula --(CH.sub.2).sub.p --CH(R.sub.6)--X.sub.1 or --CH(R.sub.6)--X.sub.2, in which p is one of the numbers 1, 2 or 3, X.sub.1 is halogen, cyano, --OR.sub.7, --OC(O)R.sub.7, --OC(O)N(R.sub.7)(R.sub.8), --C(O)OR.sub.7 or --C(O)N(R.sub.7)(R.sub.8), X.sub.2 is halogen, cyano, 1,2-epoxyethyl, --C(O)OR.sub.7 or --C(O)N(R.sub.7)(R.sub.8) and R.sub.6 is hydrogen, methyl or phenyl, R.sub.7 being hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, phenyl, C.sub.7 -C.sub.14 -alkaryl or C.sub.7 -C.sub.14 -aralkyl and R.sub.8 being hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sub.7 and R.sub.8, together with the nitrogen atom to which they are bonded, forming a 5-membered or 6-membered heterocyclic ring, or R.sub.2 is a group of the formula II
- L--CO-- (II)
- in which L is hydrogen, C.sub.1 --C.sub.12 -alkyl, C.sub.2 --C.sub.12 -alkenyl, C.sub.3 -C.sub.4 -alkynyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.7 -C.sub.14 -alkaryl, C.sub.7 -C.sub.14 -aralkyl, chloromethyl, unsubstituted phenyl, phenyl which is substituted by two C.sub.1 -C.sub.4 -alkyls and one hydroxyl, or a group --OR.sub.9, in which R.sub.9 is C.sub.1 -C.sub.12 -alkyl, cyclohexyl, C.sub.2 -C.sub.12 -alkenyl, benzyl or phenyl, or L is a group of the formula III ##STR62## or R.sub.2 is a group of the formula IV ##STR63## in which R.sub.10 and R.sub.11 independently of one another are C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, phenyl, C.sub.7 -C.sub.14 -alkaryl or C.sub.7 -C.sub.14 -aralkyl and R.sub.11 additionally can also be hydrogen, or R.sub.2 is a group of the formula V ##STR64## in which A' is methylene or a group --CH.sub.2 --CH(R.sub.13)-- and q is zero or 1, and R.sub.12 and R.sub.13 independently of one another are hydrogen, methyl, ethyl, phenoxymethyl or phenyl, or R.sub.2 is a group of the formula VI ##STR65## in which B is a group C.sub.r H.sub.2r, in which r is a number from 2 to 12, or is C.sub.4 -C.sub.8 -alkenylene, C.sub.4 -C.sub.8 -alkynylene, phenylene, xylylene, bitolylene, C.sub.5 -C.sub.12 -cycloalkylene or a group --CONH--B.sub.1 --NHCO--, in which B.sub.1 is a group C.sub.r H.sub.2r, phenylene, naphthylene, tolylene or a group of the formulae ##STR66## in which R' is hydrogen, methyl or ethyl, R" is hydrogen or methyl and r is as defined above, or R.sub.2 is one of the groups --S(O).sub.z R.sub.14 or --OR.sub.15, in which z is the number 1 or 2, R.sub.14 is C.sub.1 -C.sub.12 -alkyl, C.sub.7 -C.sub.14 -alkaryl or phenyl and R.sub.15 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.7 -C.sub.14 -aralkyl or a group of the formula L'--CO--, in which L' is as defined above for L, R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.7 -C.sub.14 -aralkyl, C.sub.7 -C.sub.14 alkaryl or phenyl and R.sub.4 can additionally also be hydrogen or a group of the formula Ia ##STR67## in which R.sub.1, R.sub.2, R.sub.3, R.sub.5, A, Y, m and n are as defined herein and M is a direct bond, ##STR68## and D.sub.1 and D.sub.2 independently of one another are hydrogen, C.sub.1 -C.sub.18 -alkyl, alkyl interrupted by 1 to 3 --S-- or phenyl, or D.sub.1 and D.sub.2, together with the C atom linking them, form a 5-membered or 6-membered aliphatic ring and D.sub.3 is hydrogen, C.sub.1 -C.sub.18 -alkyl or phenyl, Y is --O-- or --N(R.sub.16)--, in which R.sub.16 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, phenyl, C.sub.7 -C.sub.14 -alkaryl, C.sub.7 -C.sub.14 -aralkyl, C.sub.3 -C.sub.11 -alkoxyalkyl, a group of the formula VII ##STR69## or a group --Z--D, in which Z is a --(CH.sub.2).sub.s group unsubstituted or substituted by a methyl group, s being one of the numbers 2 to 4 and D being hydroxyl, --OR.sub.7 or --N(R.sub.18)(R.sub.19), in which R.sub.17 and R.sub.18 are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl or a group of the formula VIII ##STR70## and R.sub.17 additionally can also be a group of the formula VII, R.sub.19 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl or a group of the formula IX ##STR71## or R.sub.18 and R.sub.19, together with the nitrogen atom to which they are bonded, form a 5-membered or 6-membered heterocyclic ring, or R.sub.16 is a group of the formula IXa ##STR72## in which Q is as defined above for B, n and m independently of one another are zero or 1, and A is methylene or a group --CH.sub.2 --CH(R.sub.20)-- or --CH.sub.2 --C(E)(G)--, in which R.sub.20 is hydrogen, methyl, ethyl, phenoxymethyl or phenyl, E is cyano or a group --C(O)OR.sub.21, --C(O)R.sub.22, --SO.sub.2 R.sub.22, --P(O)-- --(OR.sub.23).sub.2, --C(O)NR.sub.24 R.sub.25 or --CHO, in which R.sub.21 is C.sub.1 -C.sub.4 -alkyl, R.sub.22 is C.sub.1 -C.sub.12 -alkyl, C.sub.7 -C.sub.14 -alkaryl or phenyl, R.sub.23 is C.sub.1 -C.sub.18 -alkyl, phenyl or allyl, and R.sub.24 and R.sub.25 independently of one another are hydrogen, C.sub.1 -C.sub.18 -alkyl or phenyl, and G is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.3 -C.sub.4 -alkynyl, C.sub.5 -C.sub.12 -cycloalkyl, C.sub.6 -C.sub.18 -alkylcycloalkyl, C.sub.6 -C.sub.14 -cycloalkylalkyl, C.sub.7 -C.sub.14 -aralkyl, C.sub.7 -C.sub.19 -alkylaralkyl, phenyl, or C.sub.1 -C.sub.18 -alkyl which is substituted by phenoxy, C.sub.7 -C.sub.10 -alkylphenoxy, benzyloxy, cyclohexyloxy, cyano, --COOR.sub.26, --OCOR.sub.27 or --P(O)(OR.sub.28).sub.2, R.sub.26 being C.sub.1 -C.sub.18 -alkyl or C.sub.3 -C.sub.12 -cycloalkyl, R.sub.27 being C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, phenyl, C.sub.7 -C.sub.14 -aralkyl or a group of the formula III and R.sub.28 being C.sub.1 -C.sub.18 -alkyl, allyl or phenyl, or G is C.sub.2 -C.sub.18 -alkyl interrupted by --O--, --S--, --SO-- or --SO.sub.2 -- or a group of the formula ##STR73## in which R.sub.29 and R.sub.30 independently of one another are C.sub.1 -C.sub.4 -alkyl and R.sub.30 additionally can also be hydrogen, or, if E is a group --C(O)R.sub.22, G and R.sub.22 together are trimethylene or tetramethylene.
Dependencies are inferred from the claim text.