US3050393A - Filter layer for photographic elements - Google Patents

Filter layer for photographic elements Download PDF

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Publication number
US3050393A
US3050393A US31809A US3180960A US3050393A US 3050393 A US3050393 A US 3050393A US 31809 A US31809 A US 31809A US 3180960 A US3180960 A US 3180960A US 3050393 A US3050393 A US 3050393A
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United States
Prior art keywords
parts
dye
layer
solution
water
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Expired - Lifetime
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US31809A
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English (en)
Inventor
Macdonald Eric
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Ilford Imaging UK Ltd
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Ilford Ltd
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B50/00—Formazane dyes; Tetrazolium dyes
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor

Definitions

  • This invention relates to photographic materials which comprise a support and one ormore photographic emulsion layers and which include a colour filter layer.
  • the colour of the filter layers must be capable of ready removal or discharge.
  • a yellow. colloidal silver layer is employed, for example, the usual step of removing developed silver from the material after the colour images have been formed therein, also removes the colloidal silver.
  • colloidal silver filter layers are not without their disadvantages since they have some tendency to interfere with the processing of the multilayer assembly. It is an object of the present invention to provide photographic materials containing filter layers wherein the filter layers contain dyestuffs which are readily discharged without departure from the usual processing techniques employed,
  • Preferred compounds are those in which R is phenyl, halophenyl, sulphophenyl or alkylphenyl, R is hydrogen or an alkyl group containing up to 4 carbon atoms, and R is phenyl, carboxyphenyl, alkylphenyl (the alkyl group containing up to 4 carbon atoms), or sulphonamidophenyl.
  • Suitable dyes are those known as formazan dyes, for a description of which reference may be made to Chemical Reviews, 1955, page 357. Dyes which contain two units of the chromophoric structure referred to above are included in this class.
  • a photographic material comprising a support carrying three silver halide emulsion layers, one of which, being other than the middle layer of the three, is sensitive to blue light but is otherwise unsensitised, one of which is sensitive to green light, and one of which is sensitive to 2 red light, and a yellow filter layer located between said 'blue sensitive emulsion layer and the other emulsion layers, said yellow filter layer comprising a colloid material, preferably gelatin, containing a dye which has the chromophonic structure defined above and is yellow in colour.
  • a photographic material comprising a support carrying, in order, a silver halide emulsion layer sensitive to red light but partially sensitive to green light, a filter layer containing a magenta formazan dye which has the chromophoric structure defined above and is magenta in colour, a green sensitised silver halide emulsion layer, a filter layer containing a formazan dye which has the structure defined above and is yellow in colour, and finally blue sensitive silver halide emulsion layer.
  • the dye used should be non-migratory in the colloid, e.g. gelatin, in which it is present, so that it cannot wander freely from layer to layer.
  • the dye may be dissolved in a water-immiscible oil and dispersed in the form of fine droplets in the colloid medium, or the dye may advantageously include in its molecule a group or groups known to impart non-ditfusibility in a colloid medium, e.g. long chain alkyl groups such as stearyl groups.
  • the dye also contains a solubilising group, e.g. a sulphonic or carboxylic acid group so that the dye may conveniently be dissolved as the ammonium or alkali metal salt for addition to the colloid.
  • the formazan dyes have excellent tinctorial power and so may be coated in thin colloid layers to give a high filter density. It is an advantage of the non-diffusible filter layers of this invention that their colour due to the said dyestutfs is rapidly and completely discharged by an alkaline potassium fern'cyanide bath which may be used (at the same time as one of the steps) in the removal of silver from colour processed materials. Accordingly, in use, they do not require the provision of any separate step to efiect discharge of the colour of the filter layer. It is believed that the discharge by such oxidising baths is due to the conversion of the coloured formazan dye to a corresponding colourless tetnazolium compound.
  • EXAMPLE 1 Preparation of the Insoluble Formazan Qt r 3.2 parts of o-chloraniline are suspended in 20 parts of water and 10 parts of concentrated hydrochloric acid. The amine is diazotised at 5 by the rapid'addition of 50 parts of an N/2 solution of sodium nitrite. The. diazo solution is added dropwise to a solution of 3.35 parts of acetaldehyde'phenyl hydrazone in parts of pyridine over 5 minutes at room temperature, 50 parts of Water are added and the dye precipitated is collected by filtration and washed with water to yield 5.82 parts of a reddish solid of M.Pt. 1
  • the dye I may be dispersed in gelation by any conventional means, e.g. a solution in ethyl acetate or other low boiling solvent may be added with a dispersing agent such as Aerosol OT to a gelation solution and homogenised. A coating of this dyed gel on film base on drying yields an orange-yellow layer which is rapidly dis- EXAMPLE 2 7 Preparation of the Soluble Formazan 5.0 parts of pure metanilic acid in 5.0 parts of water is dissolved by the addition of the minimum quantity of dilute sodium hydroxide solution.
  • a dispersing agent such as Aerosol OT
  • the dyell may be coated in gelatin or silver halide emulsion in asimilar fashion to any other soluble dyestufi,'e.g. 1.0 part of the dye llsuspended in 100 parts of water is dissolved by the addition of 3 to 4 parts of a N solution'of sodium hydroxide. The solution is added to 200 parts of a solution of gelatin at 40, diluted as required and coated on film base or other. substrate to yield a yellow layer with 7x max 420 m 'Ihe'dye is rapidly washed out of the layer with water in ca 30 secs.
  • the dye 111 may be dispersed by any conventional means in gelatin and coated to yield a magenta layer with a broad absorption band max 525 mu. 7
  • dye III there may be used 1-4',-toly1-3- (4" dodecoxyphenyl) 5 phenylformazan, 3 undecyl 1:5 diphenylformazan, 1 phenyl 3 undecyl 5 (4' sulphonamidophenyl)formazan, or 1 phenyl 3 r undecyl-5-(1'-naphthyl)formazan.
  • EXAMPLE 4 Preparation of a Formazan Containing Groups Conferring Alkali Solubility and Non-Diflusibility 4-dodecylaniline-3-sulphonic acid sodium salt (4.5 pants) is dissolved in water (100 parts) and 25 parts of an aqueous N/ 2 sodium nitrite solution added. The solution at 30 is added dropwise to an ice cold solutionof concentrated hydrochloric acid (5 parts) and water (100 parts);
  • the reaction solution is diluted with 500 parts of water, the dyestutf potted out with 20 parts of crystalline sodium acetate and collected by filtration.
  • the dye VI may be dispersed by conventional means in gelatin and coated to yield a yellow layer with A max 430 m EXAMPLE 9
  • the diazo paste from 4.5 parts of 4-dodecylaniline-3-sulphonic acid sodium salt is condensed with (a) 2.05 parts of acetaldehyde-ptolylhydrazone to give 5.3 parts of a yellow formazan dye, A max in gelatin 421 m (b) 2.21 parts of acetaldehyde-p-chlorphenylhydrazine to give 5.5 parts of a yellow formazan dye.
  • a photographic material which comprises a support 4 carrying at least one silver halide emulsion layer and a filte'r layer formed of a colloid containing a dye of the general formula:
  • X and Y are each selected from hydrogen, halogen, alkyl, alkoxy, sulphonic, sulphonylamido and carboxylic groups, and R is selected from hydrogen, alkyl and aryl groups.
  • a photographic material according to claim 1 wherein the dye is the compound of the formula-:
  • Glafkides Photographic Chemistry, vol. 2, page 5 61, Foundation Press, London (1960); translation from the 2nd French edition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US31809A 1959-06-26 1960-05-26 Filter layer for photographic elements Expired - Lifetime US3050393A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22093/59A GB884494A (en) 1959-06-26 1959-06-26 Improvements in or relating to photographic materials

Publications (1)

Publication Number Publication Date
US3050393A true US3050393A (en) 1962-08-21

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US31809A Expired - Lifetime US3050393A (en) 1959-06-26 1960-05-26 Filter layer for photographic elements

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US (1) US3050393A (sr)
DE (1) DE1146753B (sr)
ES (1) ES259131A1 (sr)
GB (1) GB884494A (sr)
NL (1) NL253100A (sr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3227556A (en) * 1962-12-11 1966-01-04 Eastman Kodak Co Photosensitive elements containing formazans
US4196002A (en) * 1977-09-19 1980-04-01 Eastman Kodak Company Photothermographic element containing heat sensitive dye materials
US4201590A (en) * 1977-09-19 1980-05-06 Eastman Kodak Company Heat sensitive reactive products of hexaarylbiimidazole and antihalation dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3503741A (en) * 1966-11-04 1970-03-31 Eastman Kodak Co Silver-dye-bleach process utilizing formazan dyes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2231684A (en) * 1936-05-09 1941-02-11 Eastman Kodak Co Monopack film sensitized with layers containing different silver halides
US2298731A (en) * 1939-02-17 1942-10-13 Eastman Kodak Co Pyrrole filter and backing dye
US2647833A (en) * 1949-02-09 1953-08-04 Ilford Ltd Color photographic film and process

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2390707A (en) * 1944-04-19 1945-12-11 Gen Aniline & Film Corp Photographic filter and antihalation layers
US2752244A (en) * 1955-02-23 1956-06-26 Gen Aniline & Film Corp Method and compounds for discharging filter dyes in photographic film
DE1049700B (sr) * 1957-02-18

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2231684A (en) * 1936-05-09 1941-02-11 Eastman Kodak Co Monopack film sensitized with layers containing different silver halides
US2298731A (en) * 1939-02-17 1942-10-13 Eastman Kodak Co Pyrrole filter and backing dye
US2647833A (en) * 1949-02-09 1953-08-04 Ilford Ltd Color photographic film and process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3227556A (en) * 1962-12-11 1966-01-04 Eastman Kodak Co Photosensitive elements containing formazans
US4196002A (en) * 1977-09-19 1980-04-01 Eastman Kodak Company Photothermographic element containing heat sensitive dye materials
US4201590A (en) * 1977-09-19 1980-05-06 Eastman Kodak Company Heat sensitive reactive products of hexaarylbiimidazole and antihalation dyes

Also Published As

Publication number Publication date
DE1146753B (de) 1963-04-04
NL253100A (sr)
GB884494A (en) 1961-12-13
ES259131A1 (es) 1960-10-01

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