Color-photographic recording material

Claim 2

A colour-photographic recording material which, in at least a light-sensitive silver halide emulsion layer, an intermediate layer, an image-receiving layer/and or a protective layer, contains, as a stabiliser, a light stabilizing amount of at least one s-triazone compound which contains in its molecule at least one sterically hindered phenol group and at least one polyalkylpiperidine group.

Claim 3

A colour-photographic recording material according to claim 1, which contains, as a stabiliser, a compound of the formulae I, II or III ##STR63## in which R I , R II and R III , independently of one another, are each either (a) a group of the formulae IV, V, VI or VIa ##STR64## in which p is zero or an integer of from 1-12, r is an integer from 2-6, X is --O--, --S-- or --NR 5 --, X' is --O-- or --NR 5 --, K is a direct bond, C 1 -C 6 -alkylene or a group of the formula ##STR65## R 1 is hydrogen, C 1 -C 8 -alkyl, C 5 -C 8 -cycloalkyl, C 7 -C 9 -phenylalkyl, phenyl or C 7 -C 10 -alkylphenyl, R 2 is C 1 -C 8 -alkyl, C 5 -C 8 -cycloalkyl, C 7 -C 9 -phenylalkyl, phenyl or C 7 -C 10 -alkylphenyl, R 3 is hydrogen or methyl, R 4 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, phenyl or benzyl, R 5 is hydrogen, C 1 -C 12 -alkyl, C 1 -C 12 -cycloalkyl, allyl or benzyl, and L is --CN, --COCH 3 or --SO 2 CH 3 , or (b) a group of the formulae VII to XV ##STR66## in which Y and Y', independently of each other, are each --O-- or --N(R 6 )--, R 6 is hydrogen, C 1 -C 18 -alkyl, C 3 -C 6 -alkenyl, C 5 -C 12 -cycloalkyl, C 7 -C 12 -phenylalkyl, C 3 -C 12 -alkoxyalkyl, C 4 -C 12 -dialkylaminoalkyl, a group of the formula --C s H 2s --X'--CO--R 14 or ##STR67## or a group of the formula XVI ##STR68## R is hydrogen, or methyl, R 7 is hydroxyl, C 1 -C 12 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 4 -alkynyl, C 7 -C 12 -phenylalkyl, glycidyl, C 1 -C 4 -alkyl which is substituted by halogen, --CN, --COOR 15 or --CON(R 16 )(R 17 ), a group of the formula --CO--R 14 , --CO--OR 15 , --CO--N(R 16 )(R 17 ), --CH 2 --CH(R 18 )--OR 19 , --SO--R 20 , --SO 2 --R 20 , --OR 15 or --OOC--R 14 , R 8 is hydrogen, --CN, --COOR 15 , CONH 2 or --CON(R 16 )(R 17 ), R 9 is methyl or ethyl, R 10 is hydrogen, C 1 --C 12 -alkyl, C 5 --C 8 -cycloalkyl or benzyl, and R 11 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl or phenyl, or R 10 and R 11 , together with the C atom to which they are bonded, are a C 5 --C 12 -cycloalkane or alkylcycloalkane ring, R 12 is hydrogen, --OR 21 , --OOC--R 14 or --N(R 22 )--CO--R 14 , and R 13 is hydrogen, --CN, --COOR 15 , --CONH 2 or --CON(R 16 )(R 17 ), or R 12 and R 13 are together a group of the formulae ##STR69## q is 1 or 2, s is an integer from 2-6, Y" is --O-- or --NR 5a --, in which R 5a is defined in the same way as R 5 or is a group of the formula XVI, R 14 is hydrogen, C 1 -C 12 -alkyl, C 2 -C 6 -alkenyl, chloromethyl, C 5 -C 12 -cycloalkyl, C 7 -C 12 -phenylalkyl, phenyl, C 7 -C 10 -alkylphenyl or such phenyl, phenylmethyl or phenylethyl as is substituted by 1 or 2 C 1 -C 4 -alkyl groups and a hydroxyl group, R 15 is C 1 -C 12 -alkyl, allyl, benzyl or cyclohexyl, R 16 is C 1 -C 12 -alkyl, allyl, cyclohexyl, benzyl or phenyl, and R 17 is hydrogen, C 1 -C 8 -alkyl or allyl, or R 16 and R 17 , together with the N atom, are a 5- or 6-membered heterocyclic ring, R 18 is hydrogen, C 1 -C 4 -alkyl, C 2 ∝C 13 -alkoxymethyl, phenyl or phenoxymethyl, R 19 is hydrogen, C 1 -C 12 -alkyl, --CO--R 14 or --CO--N(R 16 )(R 17 ), R 20 is C 1 -C 12 -alkyl, phenyl or C 7 -C 22 -alkylaryl, R 21 is hydrogen, C 1 -C 12 -alkyl, allyl or benzyl, R 22 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 12 -cycloalkyl or benzyl, R 23 is hydrogen, methyl or ethyl, R 24 and R 24a , independently of each other, are each H or C 1 -C 4 -alkyl, and R 25 is hydrogen, C.sub. -C 12 -alkyl, C 3 -C 12 -alkoxyalkyl, C 5 -C 12 -cycloalkyl, allyl or benzyl, or (c) a group of the formula --OR 26 , --SR 27 , --P(O)(OR 28 ) 2 or --N(R 29 )(R 30 ), in which R 26 is hydrogen, C 1 -C 18 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 12 -alkoxyalkyl, C 4 -C 12 -dialkylaminoalkyl, phenyl, C 7 -C 22 -alkylaryl, C 7 -C 9 -phenylalkyl or C 5 -C 12 -cycloalkyl, R 27 is C 1 -C 18 -alkyl, C 5 -C 12 -cycloalkyl, phenyl, C 7 -C 12 -alkylphenyl, C 7 -C 9 -phenylalkyl, --CH 2 COOR 31 or --CH 2 CH 2 COOR 31 , R 31 is hydrogen or C 1 -C 12 -alkyl, R 28 is C 1 -C 12 -alkyl, phenyl, tolyl, benzyl or a group of the formula XVI, R 29 and R 30 , independently of each other, are each hydrogen, C 1 -C 12 -alkyl, C 2 -C 4 -alkyl which is substituted by C 1 -C 4 -alkoxy, R 14 --COO-- or C 2 - C 8 - dialkylamino, C 5 -C 12 -cycloalkyl, C 3 -C 6 -alkenyl or C 7 -C 9 -phenylalkyl, or R 29 and R 30 , together with the N atom to which they are bonded, are a 5- or 6-membered heterocyclic ring, and R III can also be a group of the formula XVII ##STR70## in which t is 1, 2 or 3, A is a direct bond, a --(CH 2 ) q --group or a --Y'--C s H 2s --group, and M, if t=1, is a divalent group, C 2 -C 12 -alkylene, C 4 -C 8 -alkenylene, xylylene or a radical of the formula --CH 2 --C.tbd.C--CH 2 -- ##STR71## --CH 2 --COO--B--OOC--CH 2 --, --CH 2 --CH(OH)--CH 2 --, --CH 2 CH(OH)CH 2 --D--CH 2 CH(OH)CH 2 --, --CH 2 --CH(R 18 )--OOC--R 33 --COO--CH(R 18 )--CH 2 -- or --CO--NH--G--NH--CO--, in which B is C 2 -C 12 -alkylene, C 4 -C 8 -oxaalkylene or cyclohexylene, D is a divalent radical of the formula --O--R 32 --O-- or --OOC--R 33 --COO--, in which R 32 is C 2 -C 12 -alkylene, C 6 -C 12 -cycloalkylene, C 6 -C 12 -arylene or -phenylene-Z-phenylene, and Z is --O--, --CH 2 --, >C(CH 3 ) 2 or --SO 2 , R 33 is a direct bond, C 1 -C 12 -alkylene, C 2 -C 6 -alkenylene, C 6 -C 12 -cycloalkylene or cycloalkenylene or C 6 -C 12 -arylene, and G is a divalent aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic radical having 6- 15 C atoms, M, if t=2, is a trivalent radical of the formula T--CH.sub.2 CH(OH)CH.sub.2 ].sub.3 or R.sup.34 --COO--CH(R.sup.18 )--CH.sub.2 ].sub.3 in which T is a trivalent radical of the formulae ##STR72##

Claim 4

and R 34 is a trivalent aliphatic hydrocarbon radical having 3-10 carbon atoms or a trivalent aromatic hydrocarbon radical having 6-10 C atoms, and M, if t=3, is a tetravalent radical of the formula Q--CH.sub.2 CH(OH)CH.sub.2 ].sub.4 or R.sup.35 --COO--CH(R.sup.18)--CH.sub.2 ].sub.4 in which Q is a group of the formula ##STR73## and R 35 is a tetravalent aliphatic hydrocarbon radical having 4-10 C atoms or a tetravalent aromatic hydrocarbon radical having 6-12 C atoms, R IV is the m-valent radical of a polyamine or of a polyol, and m is an integer from 2 to 6, R V is a divalent group of the formula --Y--R 36 --Y-- or ##STR74## in which R 36 is C 2 -C 12 -alkylene, C 5 -C 12 -cycloalkylene, C 8 -C 12 -aralkylene, C 6 -C 12 -arylene, C 4 -C 8 -alkylene which is interrupted by O or NR 5 or a group of the formula ##STR75## in which M' is a divalent group of the formula M, and R 36a is C 2 -C 12 -alkylene, C 5 -C 12 -cycloalkylene, C 8 -C 12 -aralkylene, C 6 -C 12 -arylene or C 4 -C 8 -alkylene which is interrupted by O or NR 5 , n is 2 to 50, and E and E' are each terminal groups, and at least one of the radicals R I , R II and R III contains a sterically hindered phenol group and at least one of the radicals R I , R II , R III , R IV and R V contains a polyalkylpiperidine radical.

Claim 5

and R 34 is a trivalent aliphatic hydrocarbon radical having 3-10 carbon atoms or a trivalent aromatic hydrocarbon radical having 6-10 C atoms, and M, if t=3, is a tetravalent radical of the formula Q--CH.sub.2 CH(OH)CH.sub.2 ].sub.4 or R.sup.35 --COO--CH(R.sup.18)--CH.sub.2 ].sub.4 in which Q is a group of the formula ##STR73## and R 35 is a tetravalent aliphatic hydrocarbon radical having 4-10 C atoms or a tetravalent aromatic hydrocarbon radical having 6-12 C atoms, R IV is the m-valent radical of a polyamine or of a polyol, and m is an integer from 2 to 6, R V is a divalent group of the formula --Y--R 36 --Y-- or ##STR74## in which R 36 is C 2 -C 12 -alkylene, C 5 -C 12 -cycloalkylene, C 8 -C 12 -aralkylene, C 6 -C 12 -arylene, C 4 -C 8 -alkylene which is interrupted by O or NR 5 or a group of the formula ##STR75## in which M' is a divalent group of the formula M, and R 36a is C 2 -C 12 -alkylene, C 5 -C 12 -cycloalkylene, C 8 -C 12 -aralkylene, C 6 -C 12 -arylene or C 4 -C 8 -alkylene which is interrupted by O or NR 5 , n is 2 to 50, and E and E' are each terminal groups, and at least one of the radicals R I , R II and R III contains a sterically hindered phenol group and at least one of the radicals R I , R II , R III , R IV and R V contains a polyalkylpiperidine radical.

Claim 6

A colour-photographic recording material according to claim 2, which contains, as a stabiliser, a compound which is of the formula I, II or III and which contains in its molecule at least one sterically hindered phenol group and at least one N-substituted 2,2,6,6-tetramethylpiperidine group.

Claim 7

A colour-photographic recording material according to claim 2, which contains, as a stabiliser, a compound of the formula I in which R I , R II and R III , independently of one another, are each (a) a group of the formula IVa ##STR76## in which p is an integer from 1 to 4, and X, R 1 and R 2 are as defined in claim 2, (b) a group of the formulae VIIa or XVa ##STR77## in which Y is --O-- or --NR 6 --, and R 6 , R 7 , R 12 and s are as defined in claim 2, or (c) a group of the formula --OR 26 , --SR 27 , --P(O) (OR 28 ) 2 or --N(R 29 ) (R 30 ), in which R 26 , R 27 , R 28 , R 29 and R 30 are as defined in claim 2, and at least one of the radicals R I , R II and R III contains a sterically hindered phenol group, and at least one of the radicals R I , R II and R III contains an N-substituted 2,2,6,6-tetramethylpiperidine group.

Claim 8

A colour-photographic recording material according to claim 4, which contains, as a stabiliser, a compound of the formula I in which R I , R II and R III , independently of one another, are each (a) a group of the formula IVa in which R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is C 1 -C 4 -alkyl, and X and p are as defined in claim 4, or (b) a group of the formula VIIa or XVa in which Y is --O-- or --NR 6 --, R 6 is hydrogen, C 1 -C 8 -alkyl, allyl, cyclohexyl, benzyl or a group of the formula --C s H 2s --X'--CO--R 14 in which s=2 or 3, X' is --O-- and R 14 is such phenyl, phenylmethyl or phenylethyl as is substituted by 1 or 2 C 1 -C 4 -alkyl groups and a hydroxyl group, R 7 is methyl, allyl, benzyl, 2-hydroxyethyl, acetyl, acryloyl or a group of the formula --CON(R 16 )(R 17 ) in which R 16 is C 1 -C 8 -alkyl, cyclohexyl or phenyl, and R 17 is hydrogen or C 1 -C 8 -alkyl, and R 12 is hydrogen, or (c) a group of the formula --OR 26 , --SR 27 or --N(R 29 )(R 30 ) in which R 26 is C 1 -C 12 -alkyl, phenyl, C 7 -C 22 -alkylaryl, benzyl or cyclohexyl, R 27 is C 1 -C 12 -alkyl, cyclohexyl, phenyl, --CH 2 COO(C 1 -C 12 -alkyl) or --CH 2 CH 2 COO(C 1 -C 12 -alkyl), and R 29 and R 30 are each hydrogen, C 1 -C 12 -alkyl, benzyl or allyl.

Claim 9

A colour-photographic recording material according to claim 2, which contains, as a stabiliser, a compound of the formula II in which m=2 and R IV is a divalent group of the formula ##STR78## in which R 37 is C 2 -C 12 -alkylene, C 4 -C 8 -alkylene which is interrupted by --O-- or --NR 5 --, C 6 -C 15 -arylene, C 8 -C 12 -aralkylene or C 5 -C 12 -cycloalkylene, and R 5 and R 6 are as defined in claim 2.

Claim 10

A colour-photographic recording material according to claim 2, which contains, as a stabiliser, a compound of the formula II in which m=3 and R IV is a trivalent group of the formula ##STR79## or m=4 and R IV is a tetravalent group of the formula ##STR80## in which a is 2 or 3, b is 2-12, and R 6 is as defined in claim 2.

Claim 11

A colour-photographic recording material according to claim 2, which contains, as a stabiliser, a compound of the formula III in which R V is a divalent group of the formula --N(R 6 )--R 36a --N(R 6 )-- in which R 36a and R 6 are as defined in claim 2.

Claim 12

A colour-photographic recording material according to claim 8, wherein, in the compound of the formula III, the terminal group E is hydrogen and the terminal group E' is a group of the formula --N(R 6 )--R 36a --NHR 6 .

Claim 13

A colour-photographic recording material according to claim 8, which contains, as a stabiliser, a compound of the formula III in which R I is a group of the formula ##STR81## and R V is a group of the formula ##STR82## in which w is 2-6.

Claim 14

A colour-photographic recording material according to claim 10, which contains, as a stabiliser, a compound of the formula III in which R I is a group of the formula ##STR83## and R V is a group of the formula ##STR84## in which p is 1-4, X is --O--, --S--, --NH-- or --N(C 1 -C 4 -alkyl)-, R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is C 1 -C 4 -alkyl, w is 2-6 and R 7 is methyl, allyl, benzyl, 2-hydroxyethyl, acetyl, aryloyl or a group of the formula --CON(R 16 )(R 17 ) in which R 16 is C 1 -C 8 -alkyl, cyclohexyl or phenyl and R 17 is hydrogen or C 1 -C 8 -alkyl.

Claim 15

A colour-photographic recording material according to claim 1, which, in addition to a stabiliser of the formula I, II or III, contains an optical stabiliser from the class of the ultraviolet absorbers.

Claim 16

A colour-photographic recording material according to claim 1, which contains 1 to 2,000 mg of compound of the formula I, II or III per m 2 .