Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39296—Combination of additives
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/39212—Carbocyclic
  • G03C7/39216—Carbocyclic with OH groups
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3924—Heterocyclic
  • G03C7/39244—Heterocyclic the nucleus containing only nitrogen as hetero atoms
  • G03C7/39248—Heterocyclic the nucleus containing only nitrogen as hetero atoms one nitrogen atom
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3924—Heterocyclic
  • G03C7/39244—Heterocyclic the nucleus containing only nitrogen as hetero atoms
  • G03C7/39256—Heterocyclic the nucleus containing only nitrogen as hetero atoms three nitrogen atoms
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
  • G03C7/392—Additives
  • G03C7/39208—Organic compounds
  • G03C7/3928—Spiro-condensed
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/132—Anti-ultraviolet fading
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/162—Protective or antiabrasion layer

Definitions

• the present application relates to a color photographic recording material which contains, in at least one light-sensitive silver halide emulsion layer and / or in at least one of the customary auxiliary layers for stabilization, a mixture of a polyalkylpiperidine light stabilizer specifically substituted on the piperidine nitrogen and a phenolic antioxidant.
• polyalkylpiperidine light stabilizer specifically substituted on the piperidine nitrogen and a phenolic antioxidant.
• polyalkylpiperidines are generally known as light stabilizers for organic materials, in particular for polymers. It has also already been proposed in DE-OS 2 126 954 to use such polyalkylpiperidines as agents against the fading of color photographs. It was further proposed in EP-A 11051 to use certain polyalkylpiperidine derivatives containing at least one phenol group as light stabilizers for color photographs. These are polyalkylpiperidine esters of hydroxylbenzylmalonic acids.
• polyalkylpiperidine compounds to be used according to the invention as component i) include in particular the following classes of compounds
• any substituents are alkyl, they are straight-chain or branched alkyl groups. If they are C 1 -C 4 alkyl, then it is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl. If they are C 1 -C 8 alkyl, n-pentyl, 2,2-dimethylpropyl, n-hexyl, 2,3-dimethylbutyl, n-octyl or 1,1,3,3-tetramethylbutyl are also suitable.
• R 23 R 3 and R 4 are C 1 -C 3 alkyl, methyl, ethyl, n-propyl and isopropyl. Methyl is preferred.
• R 10 as C 5 -C 8 cycloalkyl, for example cyclopentyl, cyclohexyl, Cycloheptyl, a-methylcyclohexyl, cyclooctyl or dimethylcyclohexyl. Cyclohexyl is preferred.
• R 10 is as C 2 -C 6 alkenyl, for example vinyl, allyl, methallyl, dimethylallyl or 2-hexenyl. Vinyl is preferred.
• R 10 is C 7 -C 14 aralkyl, it is, for example, benzyl, phenylethyl, phenylpropyl, phenylbutyl or naphthylmethyl. Benzyl is preferred.
• R 10 as C 7 -C 10 alkylphenyl is, for example, tolyl, xylyl, isopropylphenyl, tert-butylphenyl or diethylphenyl.
• R 11 is as C2-C13 alkoxymethyl, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, decyloxy or dodecyloxymethyl.
• R 13 as C 7 -C 14 alkaryl is, for example, phenyl substituted by C 1 -C 4 alkyl, such as p-tolyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4-diethylphenyl, 2,6-diethylphenyl, 4-tert-butylphenyl, 2,4-di-tert-butylphenyl or 2,6-di-tert-butylphenyl. 2,4-Di-tert-butylphenyl, 2,4-dimethylphenyl and p-tolyl are preferred.
• R 14 can be as C 2 -C 12 alkylene, for example ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
• R 14 means, for example, 2-butenylene-1,4.
• R 14 is a monovalent radical of a carboxylic acid, it represents, for example, an acetic acid, stearic acid, salicylic acid, methacrylic acid, benzoic or ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid radical .
• R 14 is a divalent radical of a dicarboxylic acid, it is, for example, a maleic, adipic, suberic, sebacic, phthalic, dibutylmalonic, dibenzylmalonic or butyl (3,5-di-tert-butyl-4-) hydroxybenzyl) malonic acid residue.
• R 14 represents a trivalent carboxylic acid residue, it means, for example, a pyromellitic acid residue.
• R 14 is a divalent radical of a dicarbamic acid, it represents, for example, a hexamethylene-dicarbamic acid or a 2,4-tolylene-dicarbamic acid radical.
• any substituents are C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl or C 2 -C 12 alkylene, they have the meaning already given under a).
• R 15 is in particular phenylethyl or especially benzyl.
• R 15 as C 2 -C 18 alkanoyl is, for example, propionyl, butyryl, octanoyl, dodecanoyl, hexadecanoyl, octadecanoyl but preferably acetyl and as C 3 -C 5 alkenoyl especially acryloyl.
• R 16 is a C 2 -C 8 alkenyl optionally substituted with a cyano, carbonyl or carbamide group, then it is, for example, 1-propenyl, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2- Octenyl, 2,2-dicyanovinyl, 1-methyl-2-cyano-2-methoxycarbonyl-vinyl, 2,2-diacetylaminovinyl.
• Any C 6 -C 15 arylene substituents are, for example, o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
• X is in particular cyclohexylene.
• polyalkylpiperidine compounds of this class are listed in Table II below.
• polyalkylpiperidine compounds of this class are listed in Table III below:
• R 25 means, for example, cyclopentylene, cyclohexylene, cyclooctylene, cyclodecylene or cyclododecylene. Cyclohexylene is preferred.
• Y is C 1 -C 18 alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 2,2-dimethylpropyl, n-hexyl, 2,3- Dimethylbutyl, n-octyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, dodecyl, hexadecyl or octadecyl.
• Y is C2-C12 alkanoyl, it is, for example, propionyl, butyryl, octanoyl, dodecanoyl, but preferably acetyl.
• polyalkylpiperidine compounds of this class are the following compounds 18 and 19
• R 28 is a group of the formula means in which R and R have the meaning given for formula I, Q is -0- or -N (R 31 ) -, AC 2 -C 6 alkylene and m are the numbers 0 or 1,
• R 31 is hydrogen, C 1 -C 12 alkyl, allyl, cyclohexyl, benzyl or C 1 - C 4 hydroxyalkyl or a group of the formula R 32 is C 1 -C 12 alkyl, allyl, cyclohexyl, benzyl, C 1 -C 4 hydroxyalkyl or
• R 31 and R 32 are C 1 -C 4 hydroxyalkyl, they are, for example, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.
• a or DC is 2 -C 6 alkylene, they are, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene or hexamethylene.
• R 31 and R 32 together represent C 4 -C 5 alkylene or oxaalkylene, this means, for example, tetramethylene, pentamethylene or 3-oxapentamethylene.
• polyalkylpiperidine compounds of this class are listed in Table IV below:
• any substituents are C 1 -C 12 alkyl, they represent, for example, methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.
• Any substituents which are C 1 -C 18 alkyl can represent, for example, the groups mentioned above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
• any groups are C 2 -C 10 alkylene, they mean, for example, ethylene, propylene, 2,2-dimethyl-propylene, tetramethylene, hexamethylene, octamethylene or decamethylene.
• R 35 as C 4 -C 18 alkyl means, for example, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-dodecyl , n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl:
• R 35 is a C 1 -C 4 alkyl substituted by -CN, it is, for example, cyanomethyl, cyanoethyl, 3-cyano-n-propyl, 4-cyano-n-butyl.
• R 35 is C 4 -C 12 alkylene, it is, for example, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
• R 35 is C 7 -C 12 aralkyl, it means in particular phenylethyl, p-methyl-benzyl or especially benzyl.
• R 36 as C 2 -C 4 alkenyl means, for example, vinyl, 1-propenyl, allyl, methallyl, 2-butenyl.
• R 38 means, for example, the groups mentioned for R 36 as alkenyl and, for example, crotyl, 2-hexenyl, 2-octenyl or 2-decenyl.
• R 38 is C 6 -C 10 aryl, it means, for example, phenyl which is unsubstituted or substituted in the o- or p-position by methyl, ethyl, isopropyl, n-butyl or tert-butyl.
• polymeric compounds selected from the group consisting of polyester, polyether, polyamides, polyamines, polyurethanes, polyureas, polyaminotriazines, poly (meth) acrylates, poly (meth) acrylamides and their copolymers, the recurring structural units of which contain a group of the formula I or above a bivalent group according to formula (I), in which R is a free valence, are connected, where R and R 1 have the meaning given for formula I.
• polyalkylpiperidine compounds of this class are the compounds of the following formulas, where m denotes the numbers 2 to about 200.
• R 41 is a radical of formula IX and wherein j is 1 or 2 and the radicals R 1 and R have the meaning defined for formula I.
• Examples of polyalkylpiperidine compounds of the formula VIII are listed in Table V below.
• polyalkylpiperidine compounds to be used as component i) according to the invention are generally known.
• the stabilizer mixture according to the invention can be incorporated into a photographic material alone or together with other compounds in a known manner.
• the mixing ratio of the polyalkylpiperidine light stabilizer i) to the phenolic antioxidant ii) varies, for example, between 90:10 and 10:90, preferably between 70:30 and 30:70.
• the stabilizer mixture is incorporated into the photographic material in the form of a dispersion, this dispersion either not containing any solvent or high or low-boiling solvent or a mixture of such solvents.
• Another suitable form of incorporation is that the stabilizers are incorporated into the photographic material alone or together with other compounds together with a polymer in the form of a latex.
• the dispersions are then used to produce the layers of color photographic recording materials.
• These layers can e.g. Intermediate or protective layers, but in particular light-sensitive (blue, green and red-sensitive) silver halide emulsion layers, in which the cyan (cyan), purple (magenta) and yellow dyes are formed during the development of the exposed recording material from the corresponding color couplers .
• the silver halide layers can contain any color couplers, in particular cyan, magenta and yellow couplers, which are used to form the dyes mentioned and thus the color formers.
• substrates solvents, polymers
• solvents, polymers are preferred which, together with the stabilizers, give the materials to be stabilized as good a resistance as possible.
• the stabilizer mixtures are incorporated in layers which additionally contain a silver halide dispersion which has been prepared and sensitized by customary methods. However, they can also be present in layers adjacent to layers containing silver halide.
• the photographic materials according to the invention have a customary structure and components which enhance or at least do not adversely affect the effectiveness of the stabilizer mixtures.
• the stabilizer mixtures containing components i) and ii) can also be combined with ultraviolet absorbers or other light stabilizers in the same layer in addition to the color couplers.
• the stabilizer mixture can also be incorporated into a receiving layer.
• the color photographic materials according to the invention can be processed in a known manner. Furthermore, they can be treated in the course or after processing in a manner which further increases their stability, for example by treatment in a stabilizer bath or the application of a protective coating.
• the invention further relates to a process for the production of color photographic images by imagewise exposure and color development of a color photographic recording material containing a stabilizer mixture with components i) and ii).
• the invention further relates to the photographic color images obtained by this process.
• the stabilizer mixtures to be used according to the invention are also suitable for protecting color-photographic layers in which the dyes are incorporated directly into the emulsion and the image is created by selective bleaching.
• the amount of stabilizer mixture can vary within wide limits and is approximately in the range from 1 to 2000 mg, preferably 100 to 800 and in particular 200 to 500 mg per m 2 of the layer into which it is incorporated.
• the photographic material contains one or more UV absorbers, this can be present together with the stabilizer mixture in one layer or in an adjacent layer.
• the amount of UV absorber can vary within wide limits and is approximately in the range of 200-2000 mg, preferably 400-1000 mg per m 2 of the layer.
• suitable UV absorbers are those of the benzophenone, acrylonitrile, thiazolidone, benzotriazole, oxazole, thiazole and imidazole type.
• the color images obtained by exposure and development with the recording material according to the invention show very good light fastness to visible and ultraviolet light.
• the stabilizer mixtures i) + ii) are practically colorless, so that there is no discoloration of the images; in addition, they are well compatible with the usual photographic additives present in the individual layers. Because of their good effectiveness, their use amount can be reduced and their precipitation or crystallization can be avoided if they are incorporated as an organic solution in the aqueous binder emulsions used for the production of photographic layers.
• the individual processing steps required to produce the color images after exposure of the photographic recording material are not adversely affected by the stabilizer mixtures i) + ii).
• drying is carried out in a drying cabinet with circulating air at room temperature.
• samples cut to 35 x 180 mm are exposed with 3000 lux ⁇ s behind a step wedge and then processed in the Ektaprint 2® process from Kodak.
• the yellow wedges obtained in this way are irradiated in an Atlas Weather-Ometer with a 2500 W xenon lamp with a total of 42 kJoules / cm 2 (a comparative sample contains no light stabilizer).
• Table 1 shows the percentage decreases in yellow density with an original reflectance density of 1.0 in blue.
• Samples are prepared and irradiated as described in Example 1, but the sterically hindered phenol and the piperidine are added in molar proportions based on the yellow coupler.
• Table 2 contains the corresponding density decreases.
• Table 3 contains the percentage density decreases obtained at the maximum with an initial reflectance density of 1.0.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Hydrogenated Pyridines (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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• 1983
  • 1983-12-12 EP EP83810582A patent/EP0114028B1/fr not_active Expired
  • 1983-12-12 DE DE8383810582T patent/DE3377596D1/de not_active Expired
  • 1983-12-14 CA CA000443245A patent/CA1203410A/fr not_active Expired
  • 1983-12-15 JP JP58235225A patent/JPS59116747A/ja active Pending
  • 1983-12-15 US US06/562,190 patent/US4517283A/en not_active Expired - Fee Related

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