Hydroquinone ether compounds

Claim 1

A colour photographic silver halide material on a support which comprises at least one colour coupler--containing silver halide emulsion layer, there being present in the silver halide emulsion layer(s) or in a layer adjacent to the silver halide emulsion layer(s) a light stabilising amount of at least one compound having the formula I ##STR40## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula II ##STR41## wherein Q is selected from the residues: (i) --COZR 4 wherein Z is --O-- or ##STR42## and R 4 independently is --H, a C 1 -C 20 straight or branched chain alkyl optionally interrupted by 1 to five oxygen atoms and optionally substituted by a group --OR 6 wherein R 6 is C 3 -C 12 cycloalkyl, straight or branched C 3 -C 20 alkenyl, C 6 -C 10 aryl optionally substituted by one or two C 1 -C 4 alkyl groups or C 7 -C 13 aralkyl, or R 4 is a C 2 -C 20 divalent straight or branched chain alkylene residue, a C 3 -C 20 straight or branched chain alkenyl group or a C 3 -C 12 cycloalkyl group; a C 6 -C 10 aryl group optionally substituted by one or two C 1 -C 8 alkyl groups or a C 7 -C 13 aralkyl group; a 5 or 6 membered heterocycle containing an oxygen atom, and optionally substituted by one or two C 1 -C 4 straight or branched chain alkyl groups; or methyl substituted by a 5 or 6 membered heterocycle containing an oxygen atom and optionally substituted by one or two C 1 -C 4 straight or branched chain alkyl groups; and when Z is --NR 5 , R 5 is hydrogen or a straight or branched chain C 1 -C 20 alkyl group or a C 5 -C 6 cycloalkyl group, or R 4 and R 5 together with the nitrogen atom to which they are each bonded may form a 5 or 6 membered heterocyclic ring, optionally substituted by one or two C 1 -C 4 alkyl groups; (ii) --OX wherein X is R 7 or --COR 7 , wherein R 7 is --H or a C 1 -C 20 straight or branched chain alkyl group, a C 3 -C 20 straight or branched chain alkenyl group, a C 3 -C 12 cycloalkyl group, a C 7 -C 13 alkyl group, or a C 6 -C 10 aryl group, optionally substituted by one or two C 1 -C 4 alkyl groups; (iii) --N(R 8 )(R 9 ) wherein R 8 and R 9 independently, are --H or a C 1 -C 20 straight or branched chain alkyl group, a C 3 -C 20 straight or branched chain alkenyl group, a C 3 -C 12 cycloalkyl group, a C 7 -C 13 aralkyl group or a C 6 -C 10 aryl group optionally substituted by one or two C 1 -C 4 alkyl groups, or an acyl group of formula --COR 7 wherein R 7 has its previous significance, or R 8 and R 9 , together with the nitrogen atom to which they are each bonded, form a 5- or 6-membered heterocyclic ring, optionally substituted by one or two C 1 -C 4 alkyl groups; (iv) --PO(OR 10 )([O] x R 11 ) wherein x is 0 or 1, and when x is 1 R 10 and R 11 are the same or different and each is --H or a straight or branched chain C 1 -C 20 alkyl group, or a C 6 -C 10 aryl optionally substituted with one or two C 1 -C 4 alkyl groups; or R 10 and R 11 may be linked together to form a C 2 -C 3 alkylene chain optionally substituted by one to four C 1 -C 20 alkyl groups; and when x is 0, R 10 has its previous significance and R 11 is a C 1 -C 5 straight chain alkyl group; (v) --SO 2 R 12 wherein R 12 is --OH, --Cl or --N(R 5 )(R 7 ) wherein R 5 and R 7 have their previous significance; provided that, when R 12 is --OH, then R 1 is a residue of formula II; (vi) --CN, halogen or --NO 2 ; and (vii) --COR 15 wherein R 15 is --H or a C 1 -C 20 straight or branched chain alkyl group or halogen; n is an integer from 1 to 20; k is 1 or 2; R 2 and R 3 are the same or different and each is straight or branched chain alkyl group having from 1 to 5 carbon atoms and, when Q is --CO 2 R 4 , either R 2 or R 3 is optionally substituted by a --CO 2 R 4 group, the R 4 groups being independent, or when Q is --COOR 4 R 2 or R 3 may be so linked to the residue C n H 2n --COOR 4 that there is formed a C 5 -C 12 cycloalkylene residue optionally substituted by another group --CO 2 R 4 the R 4 groups being independent, wherein R 4 has its previous significance; or when Q is --COR 15 , R 2 and R 3 may be so linked to the residue C n H 2n --COR 15 that there is formed a C 5 -C 12 cycloalkylene residue wherein R 15 has its previous significance; provided that, when the group Q is a --CO 2 R 4 residue wherein R 4 is a C 2 -C 20 divalent straight or branched chain alkylene residue then p and k are both 1 and the compound of formula I has the formula Ia: ##STR43## wherein R 40 is a C 2 -C 20 divalent straight or branched chain alkylene residue; and provided that, when the group Q is a --CON(R 4 )(R 5 ) residue wherein R 4 is a C 2 -C 20 divalent straight or branched chain alkylene residue and R 5 has its previous significance, then p and k are both 1 and the compound of formula I has the formula Ib: ##STR44## wherein R 2 , R 3 , q and n have their previous significance, R 41 is a C 2 -C 20 divalent straight or branched chain alkyl residue; R 1 is C 1 -C 8 straight or branched chain alkyl, C 5 -C 7 cycloalkyl optionally substituted by one or two methyl or ethyl groups, C 7 -C 9 aralkyl or a residue of formula II as hereinbefore defined, and when R 1 is a residue of formula II then R 1 and R may be the same or different; or R 1 is a residue of formula III: ##STR45## in which R and p have their previous significance; and M is a direct bond; --C(R 13 )(R 14 )-- in which R 13 and R 14 are the same or different and are hydrogen, C 1 -C 20 straight or branched chain alkyl optionally interrupted by 1 to 3 sulphur atoms, C 6 -C 10 aryl or R 13 and R 14 , together with the carbon atom to which they are attached may form a 5- or 6-membered ring which may be further substituted by one or two C 1 -C 8 straight or branched chain alkyl groups; --S--; --S--S--; --SO 2 --; --CH 2 SCH 2 --; --CH 2 OCH 2 -- or --C(CH 3 ) 2 -p-phenylen-C(CH 3 ) 2 --; R o and R oo are the same or different and each is hydrogen, a C 1 -C 20 straight or branched chain alkyl group optionally interrupted by 1 to 5 oxygen atoms, a C 3 -C 12 cycloalkyl group, a C 6 -C 10 aryl group optionally substituted by one or two C 1 -C 4 straight or branched chain alkyl groups, or a C 7 -C 13 aralkyl group provided that both of R o and R oo are not hydrogen, or R oo has its previous significance and R o is a residue of formula IV: ##STR46## in which R, R oo , R 1 and q have their previous significance, or R o and R 1 , when in ortho position to one another, together with the carbon atoms to which they are attached, may form an optionally substituted residue of formula V: ##STR47## wherein A is a carbon residue containing 4 to 20 carbon atoms which forms a substituted chroman or coumaran system, or R o and R 1 together may form a residue having the formula VI or VII: ##STR48## wherein R, R o and R oo have their previous significance, provided that the compound of formula I contains only one residue of formula III or IV; or R oo is hydrogen and R o is a residue having the formula IVa or IVb: ##STR49## wherein p, q and R have their previous significance, R 1 " is C 1 -C 8 straight or branched alkyl, C 7 -C 9 aralkyl or a residue of formula II, as hereinbefore defined, m is 1 or 2, B, when m is 1, represents C 2 -C 12 alkylene which may be interrupted by 1 to 3 oxygen or sulphur atoms, C 4 -C 10 alkenylene, C 5 -C 12 cycloalkylene, C 6 -C 12 arylene, C 8 -C 12 aralkylene, C 4-6 alkynylene, xylylene, --CH 2 CH(OH)CH 2 --, --CH 2 CH(OH)CH 2 --O--Y--O--CH 2 CH(OH)CH 2 --, ##STR50## or --CH 2 COO--B'--OCOCH 2 -- wherein Y is C 2 -C 10 alkylene, C 6 -C 12 arylene, ##STR51## or C 6 -C 12 cycloalkylene, B' is C 2 -C 8 alkylene, C 4 -C 8 oxaalkylene, or cyclohexylene and, when m is 2, B represents a group of the formula ##STR52## r is 0 to 12, R 16 represents hydrogen or straight or branched C 1 -C 12 alkyl and D is --OR 4 or --N(R 4 )(R 5 ) wherein R 4 and R 5 have their previous significance; and with the proviso that excluded from the scope of the claim are those compounds in which p is 1, q is 1, Q is COR 15 wherein R 15 is H, R o and R oo are C 1 -C 20 alkyl and R 1 is C 1 -C 8 alkyl, as well as salts of compounds of formula I with bases or organic or inorganic acids, respectively, when Q is an acidic or basic group.