US4517283A — Color-photographic recording material

Claim 1

Independent Claim 360 words

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 stabilizing amount of a stabiliser mixture comprising (i) a compound which contains at least one group of the formula I ##STR49## or a polymer, the recurring structural units of which contain a group of the formula I or are linked via a bivalent group corresponding to the formula I, in which R 1 is a free valency and in which, moreover, R is hydrogen or methyl and R 1 is methyl, a group --CH 2 --C(R 2 )═C(R 3 )(R 4 ), --CH 2 --C.tbd.C--R 5 , ##STR50## --CH 2 --COOR 7 , --CH 2 --CON(R 8 )(R 9 ), --COR 10 , --COOR 7 , --CON(R 8 )(R 9 ), --OR 7 , --CH 2 ) b OCOR 10 , --CH 2 --CH(R 11 )OR 12 , --SOR 13 or --SO 2 R 13 , a and b are 0, 1 or 2, R 2 , R 3 and R 4 independently of one another are hydrogen or C 1 -C 3 -alkyl, R 5 is hydrogen or methyl, R 6 is C 1 -C 4 -alkyl, R 7 is C 1 -C 12 -alkyl, allyl, benzyl or cyclohexyl, R 8 is C 1 -C 12 -alkyl, allyl, cyclohexyl, benzyl or phenyl, R 9 is hydrogen, C 1 -C 12 -alkyl or allyl, or R 8 and R 9 , together with the N atom to which they are linked, form a 5-membered or 6-membered heterocyclic ring, and R 10 is hydrogen, C 4 -C 12 -alkyl, C 2 -C 6 alkenyl, chloromethyl, C 5 -C 8 -cycloalkyl, C 7 -C 14 -aralkyl or C 7 -C 10 -alkylphenyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 13 -alkoxymethyl, phenyl or phenoxymethyl, R 12 is hydrogen, C 1 -C 12 -alkyl, --COR 10 or --CON(R 8 )(R 9 ) R 8 , R 9 and R 10 being as defined above, and R 13 is C 1 -C 12 -alkyl, phenyl or C 7 -C 14 -alkaryl, and (ii) a phenolic antioxidant.

Claim 2

Dependent Claim 360 words

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 stabilizing amount of a stabiliser mixture comprising (i) a compound which contains at least one group of the formula I ##STR49## or a polymer, the recurring structural units of which contain a group of the formula I or are linked via a bivalent group corresponding to the formula I, in which R 1 is a free valency and in which, moreover, R is hydrogen or methyl and R 1 is methyl, a group --CH 2 --C(R 2 )═C(R 3 )(R 4 ), --CH 2 --C.tbd.C--R 5 , ##STR50## --CH 2 --COOR 7 , --CH 2 --CON(R 8 )(R 9 ), --COR 10 , --COOR 7 , --CON(R 8 )(R 9 ), --OR 7 , --CH 2 ) b OCOR 10 , --CH 2 --CH(R 11 )OR 12 , --SOR 13 or --SO 2 R 13 , a and b are 0, 1 or 2, R 2 , R 3 and R 4 independently of one another are hydrogen or C 1 -C 3 -alkyl, R 5 is hydrogen or methyl, R 6 is C 1 -C 4 -alkyl, R 7 is C 1 -C 12 -alkyl, allyl, benzyl or cyclohexyl, R 8 is C 1 -C 12 -alkyl, allyl, cyclohexyl, benzyl or phenyl, R 9 is hydrogen, C 1 -C 12 -alkyl or allyl, or R 8 and R 9 , together with the N atom to which they are linked, form a 5-membered or 6-membered heterocyclic ring, and R 10 is hydrogen, C 4 -C 12 -alkyl, C 2 -C 6 alkenyl, chloromethyl, C 5 -C 8 -cycloalkyl, C 7 -C 14 -aralkyl or C 7 -C 10 -alkylphenyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 13 -alkoxymethyl, phenyl or phenoxymethyl, R 12 is hydrogen, C 1 -C 12 -alkyl, --COR 10 or --CON(R 8 )(R 9 ) R 8 , R 9 and R 10 being as defined above, and R 13 is C 1 -C 12 -alkyl, phenyl or C 7 -C 14 -alkaryl, and (ii) a phenolic antioxidant.

Claim 3

Dependent Claim 139 words

A colour-photographic recording material according to claim 1, wherein, in the formula I, R 1 is allyl, benzyl or a group --CH.sub.2 --COOR.sub.7, --COR.sub.10, --CON(R.sub.8)(R.sub.9), --CH.sub.2 --CH(R.sub.11)OR.sub.12, --OR.sub.7, or --CH.sub.2).sub.b OCOR.sub.10, b is 0, 1 or 2, R 7 is C 1 -C 4 -alkyl, allyl or benzyl, R 8 is C 1 -C 4 -alkyl, allyl or cyclohexyl, R 9 is C 1 -C 12 -alkyl or allyl, or R 8 and R 9 , together with the N atom to which they are linked, form a morpholine or piperidine radical, and R 10 is C 1 -C 12 -alkyl, vinyl, cyclohexyl, benzyl or phenyl, R 11 is hydrogen, methyl or phenyl and R 12 is hydrogen, methyl or a group --CON(R 8 )(R 9 ), R 8 and R 9 being as already defined in this claim.

Claim 4

Dependent Claim 170 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula II ##STR51## in which n is an integer of 1 to 4, R and R 1 are as defined for claim 1 and, with n=1, R 14 is hydrogen, C 1 -C 12 -alkyl, cyanoethyl, benzyl, glycidyl, a monovalent radical of a saturated or unsaturated aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, carbamic acid or phosphorus-containing acid or a monovalent silyl radical or, with n=2, R 14 is C 2 -C 12 -alkylene, C 4 -C 8 -alkenylene, xylylene, a divalent radical of a saturated or unsaturated aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid, dicarbamic acid or phosphorus-containing acid or a divalent silyl radical or, with n=3, R 14 is a trivalent radical of an aliphatic, cycloaliphatic or aromatic tricarboxylic acid, an aromatic tricarbamic acid or a phosphorus-containing acid or a trivalent silyl radical or, with n=4, R 14 is a tetravalent radical of an aliphatic, cycloaliphatic or aromatic tetracarboxylic acid.

Claim 5

Dependent Claim 98 words

A colour-photographic recording material according to claim 3, wherein, in the compound of the formula II, n is one of the numbers 1 or 2 and R 14 , with n=1, is a radical of an aliphatic carboxylic acid having 2-18 C atoms, a cycloaliphatic carboxylic acid having 5-12 C atoms or an aromatic carboxylic acid having 7-15 C atoms or, with n=2, is a radical of an aliphatic dicarboxylic acid having 2-12 C atoms, a cycloaliphatic or aromatic dicarboxylic acid having 8-14 C atoms or of an aliphatic, cycloaliphatic or aromatic dicarbamic acid having 8-14 C atoms.

Claim 6

Dependent Claim 228 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula III ##STR52## in which c is 1 or 2, R and R 1 are as defined in claim 1, R 15 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, C 7 -C 8 -aralkyl, C 2 -C 18 -alkanoyl or benzoyl and, with c=1, R 16 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl which is unsubstituted or substituted by a cyano group, carbonyl group or carbamide group, glycidyl, a group of the formulae --CH 2 --CH(OH)--Z, --COO--Z or --CONH--Z, in which Z is hydrogen, methyl or phenyl, and, with c=2, R 16 is C 2 -C 12 -alkylene, C 6 -C 12 -arylene, xylylene, a group --CH 2 --CH(OH)--CH 2 -- or a group --CH 2 --CH(OH)--CH 2 --O--X--O--CH 2 --CH(OH)--CH 2 --, in which X is C 2 -C 10 -alkylene, C 6 -C 15 -arylene or C 6 -C 12 -cycloalkylene, or, provided that R 15 is not alkanoyl, alkenoyl or benzoyl, R 16 can also be a divalent radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid, or, with c=1, R 15 and R 16 together can be the cyclic radical of an aliphatic or an aromatic 1,2- or 1,3-dicarboxylic acid.

Claim 7

Dependent Claim 238 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula IV ##STR53## in which R and R 1 are as defined in claim 1 and W is one of the groups ##STR54## in which R 17 is hydrogen, C 1 -C 12 -alkyl, a group --CH 2 --OCOR 22 , wherein R 22 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, cyclohexyl, phenyl, benzyl or chloromethyl, a group --CH 2 O--S(O) q R 23 , wherein R 23 is C 1 -C 4 -alkyl, p-tolyl or phenyl and q is 1 or 2, or R 17 is a group --CH 2 OCO--NHR 24 wherein R 24 is hydrogen or C 1 -C 4 -alkyl, R 18 is hydrogen or C 1 -C 4 -alkyl, R 19 is hydrogen, C 1 -C 12 -alkyl, C 3 -C 4 -alkoxyalkyl, C 5 -C 8 -cycloalkyl, allyl or benzyl, R 20 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl or benzyl, R 21 is C 1 -C 12 -alkyl, C 5 -C 8 -cycloalkyl or phenyl or R 20 and R 21 , together with the C atom to which they are linked, form a C 5 -C 12 -cycloalkane or alkylcycloalkane ring, and W can additionally also be one of the groups of the formulae ##STR55## in which g is 1 to 12.

Claim 8

Dependent Claim 149 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula V ##STR56## in which R and R 1 are as defined in claim 1 and R 25 is a group C r H 2r , in which r is an integer of from 2 to 12, or C 4 -C 8 -alkenylene, C 4 -C 8 -alkynylene, phenylene, xylylene, bitolylene, C 5 -C 12 -cycloalkylene or a group --CH 2 --CH(OY)CH 2 --(OCH 2 --CH(OY)CH 2 ) 2 --, wherein Y is hydrogen C 1 -C 18 -alkyl, allyl, benzyl, C 2 -C 12 -alkanoyl or benzoyl, or R 25 is a group --CONH--B--NHCO--, wherein B is a group C r H 2r , phenylene, naphthylene, tolylene or a group of the formulae ##STR57## in which R 26 is hydrogen or methyl and R 27 is hydrogen, methyl or ethyl.

Claim 9

Dependent Claim 235 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formulae VI ##STR58## in which d is 1 or 2 and R 28 is a group of the formula ##STR59## in which R and R 1 are as defined in claim 1, Q is --O-- or --N(R 31 )--, A is C 2 -C 6 -alkylene and m is 0 or 1, R 29 is one of the groups R 28 , --NR 31 R 32 , --OR 33 --NHCH 2 OR 33 or --N(CH 2 OR 33 ) 2 , R 30 is, with d=1, one of the groups R 28 or R 29 and, with d=2, is the group --Q--D--Q--, in which D is C 2 -C 6 -alkylene which is uninterrupted or is interrupted by --N(R 34 )--, R 31 is hydrogen, C 1 -C 12 -alkyl, allyl, cyclohexyl, benzyl or C 1 -C 4 -hydroxyalkyl or a group of the formula ##STR60## R 32 is C 1 -C 12 -alkyl, allyl, cyclohexyl, benzyl or C 1 -C 4 -hydroxyalkyl, R 33 is C 1 -C 12 -alkyl or phenyl and R 34 is hydrogen or the group --CH 2 OR 33 , or R 31 and R 32 together are C 4 -C 5 alkylene or oxaalkylene, or R 31 and R 32 can also each be a group of the formula ##STR61##

Claim 10

Dependent Claim 187 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula VII ##STR62## in which e is 1 or 2, R is hydrogen or methyl and R 35 is, with e=1, C 4 -C 18 -alkyl, C 7 -C 12 -aralkyl, a group --CO--R 36 or C 1 -C 4 -alkyl substituted by --CN, --COOR 37 , --OH, --OCOR 38 or ##STR63## in which R 36 is C 1 -C 12 -alkyl, C 2 -C 4 -alkenyl or phenyl, R 37 is C 1 -C 18 -alkyl, R 38 is C 1 -C 18 -alkyl, C 2 -C 10 -alkenyl, cyclohexyl, benzyl or C 6 -C 10 -aryl, or, with e=2, R 35 is C 4 -C 12 -alkylene, but-2-en-1,4-ylene, xylylene, one of the groups --(CH 2 ) 2 --OOC--R 39 --COO--(CH 2 ) 2 --, --CH 2 --OOC--R 40 --COO--CH 2 -- or --CH 2 --CH(OH)--CH 2 --O--R 39 --O--CH 2 --CH(OH)--CH 2 --, R 39 being C 2 -C 10 -alkylene, phenylene, cyclohexylene or 2,2-diphenylenepropane and R 40 being C 2 -C 10 -alkylene, xylylene or cyclohexylene.

Claim 11

Dependent Claim 79 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a polymeric compound selected from the group comprising polyesters, polyethers, polyamides, polyamines, polyurethanes, polyureas, polyaminotriazines, poly(meth)acrylates, poly(methy)acrylamides and copolymers thereof, the recurring structural units of which contain a group of the formula I or are linked via a bivalent group of the formula (I) in which R 1 is a free valency, R and R 1 in other respects being as defined for formula I.

Claim 12

Dependent Claim 53 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula VIII ##STR64## in which R 41 is a radical of the formula IX ##STR65## in which j is 1 or 2 and the radicals R and R 1 are as defined in claim 1.

Claim 13

Dependent Claim 69 words

A colour-photographic recording material according to claim 1, which contains, as the component (ii), a phenolic antioxidant selected from the group comprising 2,6-di-tert.-butyl-4-methylphenol, 2,2'-methylene-bis-(6-tert.-butyl-4-methylphenol), 2,2'-methylene-bis-(6-tert.-butyl-4-ethylphenol), 4,4'-methylene-bis-(2,6-di-tert.-butylphenol), 2,2-bis-(2,6-di-tert.-butyl-4-hydroxyphenyl)-propane, 2,2'-methylene-bis-[4-methyl-6-(α-methylcyclohexyl)-phenol], 1,1-bis-(5-tert.-butyl-4-hydroxy-2-methylphenyl)-butane, 1,1,3-tris-(5-tert.-butyl-4-hydroxy-2-methylphenyl)-butane, ethylene glycol bis-[3,3-bis-(3-tert.-butyl-4-hydroxyphenyl)-butyrate], 4,4'-thio-bis-(6-tert.-butyl-3-methylphenol), 1,3,5-tri-(3,5-di-tert.-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, triethylene glycol bis-(3-methyl-5-tert.-butyl-4-hydroxy-phenyl)-propionate, 1,3,5-tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)isocyanurate, diethyl 3,5-di-tert.-butyl-4-hydroxybenzylphosphonate, N,N'-di-(3,5-di-tert.-butyl-4-hydroxyphenylpropionyl)-hexamethylenediamine, 3-thia-1,5-pentanediol bis-[3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate], 1,6-hexanediol bis-[3-(2,5-di-tert.-butyl-4-hydroxyphenyl)-propionate], pentaerythritol tetrakis-[3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate], pentaerythritol tetrakis-(3,5-di-tert.-butyl-4-hydroxybenzoate), octadecyl-3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate, 2-(3,5-di-tert.-butyl-4-hydroxyanilino)-4,6-di-(octylthio)-triazine, 2,4-di-tert.-butylphenyl 3,5-di-tert.-4-hydroxybenzoate), the phenol of the formula XI, ##STR66## or the phenol of the formula X ##STR67##

Claim 14

Dependent Claim 33 words

A colour-photographic recording material according to claim 1, which contains, as the component (i) a compound of the formula C ##STR68## and, as the component (ii), a compound of the formula a ##STR69##

Claim 15

Dependent Claim 33 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula A ##STR70## and, as the component (ii), a compound of the formula b ##STR71##

Claim 16

Dependent Claim 33 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula C ##STR72## and, as the component (ii), a compound of the formula c ##STR73##

Claim 17

Dependent Claim 33 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula E ##STR74## and, as the component (ii), a compound of the formula d ##STR75##

Claim 18

Dependent Claim 33 words

A colour-photographic recording material according to claim 1, which contains, as the component (i), a compound of the formula D ##STR76## and, as the component (ii), a compound of the formula e ##STR77##

Claim 19

Dependent Claim 22 words

A colour-photographic recording material according to claim 1, which contains the stabiliser mixture (i)+(ii) in combination with cyan, magenta and yellow couplers.

Claim 20

Dependent Claim 19 words

A colour-photographic recording material according to claim 1, which contains the stabiliser mixture (i)+(ii) in combination with ultraviolet absorbers.

Claim 21

Dependent Claim 25 words

A colour-photographic recording material according to claim 19, wherein the ultraviolet absorbers are compounds of the benzophenone, acrylonitrile, thiazolidone, benzotriazole, oxazole, thiazole or imidazole types.

Claim 22

Dependent Claim 32 words

A colour-photographic recording material according to claim 1, which contains the stabiliser mixture (i) and (ii) in combination with cyan, magenta and yellow couplers and with ultraviolet absorbers in the same layer.

Claim 23

Dependent Claim 34 words

A colour-photographic recording material according to claim 1, which contains 1 to 2,000 mg of the stabiliser mixture (i) and (ii) per m 2 of the layer into which the stabiliser mixture is incorporated.

Claim 24

Dependent Claim 23 words

Process for the production of photographic colour images by imagewise exposure and colour development of 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)	1988-05-13	1988-11-12	1989-05-14	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1992-05-13	1992-11-12	1993-05-14	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1996-05-13	1996-11-12	1997-05-14	$7700.00	Window Closed / Lapsed

Color-photographic recording material

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