US3615582A - Photographic materials for the silver dye bleach process - Google Patents

Photographic materials for the silver dye bleach process Download PDF

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Publication number
US3615582A
US3615582A US778294A US3615582DA US3615582A US 3615582 A US3615582 A US 3615582A US 778294 A US778294 A US 778294A US 3615582D A US3615582D A US 3615582DA US 3615582 A US3615582 A US 3615582A
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US
United States
Prior art keywords
light
dye
sensitive emulsion
bis
silver
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US778294A
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English (en)
Inventor
Hans Vetter
Karl-Heinz Freytag
Justus Danhauser
Erich Bockly
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Agfa Gevaert AG
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Agfa Gevaert AG
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Publication date
Priority claimed from DE19671595504 external-priority patent/DE1595504B2/de
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
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Publication of US3615582A publication Critical patent/US3615582A/en
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Classifications

    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino 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
    • G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
    • G03C7/29—Azo dyes therefor

Definitions

  • PHOTOGRAPHIC MATERIALS FOR THE SILVER DYE BLEACH PROCESS This invention relates to color photographic materials for the silver-dye-bleach process which materials contain particularly light-fast yellow azo dyes.
  • color photographic images can be produced by the silver-dye-bleach process, wherein a dye, usually an azo dye, is bleached in a homogeneously dyed colloid layer in accordance with a silver image which had been produced photographically.
  • a dye usually an azo dye
  • the silver image is produced by means of a simple black-and-white development, this silver image representing a negative of the copying original. Since the image dye which is homogeneously distributed in the layer (or in the three layers of a multicolor material) is bleached proportionately to the silver image a dye image is obtained, which is positive with respect to the original.
  • a silver image is produced which is positive with respect to the original, for example, by a blackand-white reversal development or by the bromide ion diffusion method or silver salt diffusion method, then after the color bleaching a dye image is formed which is opposite in gradation to the original, that is to say a positive color image is formed if the original is a negative color image.
  • R ( 1) hydrogen, (2) an alkyl group with preferably up to three carbon atoms, (3) halogen such as chlorine or bromine, (4) an alkoxy group with preferably up to three carbon atoms, (5) an acylamino group in which the acyl groups are advantageously derived from aliphatic monoor dicarboxylic acids which have up to six carbon atoms or from benzene carboxylic acids, especially benzoic acid, or (6) an ureido group;
  • R hydrogen, an alkyl or alkoxy group having preferably up to three carbon atoms or halogen such as chlorine or bromine;
  • the dyes which are to be used according to the invention are prepared by known methods.
  • the dyes are prepared by first coupling diazotized amino arylsulfonic acids with l-amino-3-acylamino benzene compounds, reference is made to US. Pat No. 3,480,438 columns seven to nine.
  • the resulting amino azo compound is reacted with phosgene or a dicarboxylic acid chloride, such as phthalic acid chloride, or a fumaric acid chloride.
  • phosgene or a dicarboxylic acid chloride such as phthalic acid chloride, or a fumaric acid chloride.
  • U.S. Pat. No. 2,813,856 for reaction of amino azo dyes with fumaric acid chloride.
  • the dyes according to the invention can be applied in color photographic layers for the silver-dye-bleach process in various ways. As will be seen from the following examples, they are preferably employed as image dyes in layers which are subjected to a simple black-and-white development and thus form in the subsequent dye bleaching bath in a direct positive dye image. However, it is also possible to carry out a black-and-white reversal development, whereby after treatment with common dyebleaching baths, dye images with a gradation opposite to the original are obtained.
  • the dyes are substantially inert to agents customarily added to photographic layers, such as stabilizers, sensitizing dyes, chemical sensitizers, plasticizers, wetting agents, hardeners and the like.
  • bleaching baths such as those which are based on quinoline and iodide, as described in US. Pat. No. 2,629,568 (example 29) or thiourea (as indicated in British Pat. No. 507,211) and with different bleaching catalysts, such as quinoxalines or phenazine derivatives.
  • any suitable supports such as glass, baryta-coated papers, papers of all types which have been made water repellent, such as polyethylene-coated papers, cellulose acetate or polyesters and polycarbonate films and pigmented cellulose acetate films.
  • the image whites are also not discolored by exposure to light over long periods.
  • EXAMPLE I 400 ml. of a 4 percent gelatin solution containing 4.5 g. of dye l and 0.7 g. of saponin, are added to 800 ml. of a melted silver bromide gelatin emulsion. After the addition of 20 ml. of a 1 percent aqueous solution of tris-acryloylhexahydrotriazine as hardening agent one sample of the emulsion is applied onto a support of baryta-coated paper and another on to a support of cellulose triacetate in a thickness which corresponds to a silver application of 0.6 to 0.9 g. of silver per m A strip of each of the dried materials is exposed in a sensitometer customarily employed in the art behind a grey step wedge, using yellow or white light. The exposed samples are processed as follows:
  • the layers are eminently suitable for use in the production of the yellow par tial image in a multilayer photographic material.
  • EXAMPLE 2 The same procedure is employed as in example 1 but using 4.8 g. of dye 5. After exposure and processing as in example 1, baths one to six, the process is continued as follows:
  • a green-sensitive layer which contains, for every 500 ml. of the same silver bromo iodide emulsion, 15 mg. of the sensitizer of example 2 of German Pat. No. 1,177,481 and 2.5 g. of the dye of the following formula:
  • the silver is applied in a quantity of 0.75 g./m in the form of the silver halide.
  • the material After drying, the material is exposed behind a multicolored transparency and processed in the manner described in example l, with the difference that the treatment time in the dye bleaching bath is increased to 25 minutes. A color-photographic image in true colors is obtained.
  • EXAMPLE 5 The procedure is the same as that described in example 4 with the difference that the tartrazine-containing gelatin layer between the green sensitized layer and the nonsensitized emulsion layer is replaced by an arrangement of layers as follows:
  • An intermediate layer of a 2 percent gelatin solution 2.
  • R represents hydrogen, chlorine, bromine alltyl, having up to three carbon atoms, acylamino or an ureido group
  • R represents hydrogen, chlorine bromine alkyl having up to three carbon atoms or alkoxy having up to three carbon atoms and X represents carbonyl or the acyl group of a saturated or unsaturated aliphatic dicarboxylic acid or of an aromatic dicarboxylic acid.
  • R represents an acylamino group, the acyl radical of which is derived from a saturated or unsaturated monobasic or dibasic aliphatic carboxylic acid which has up to six carbon atoms.
  • the light-sensitive emulsion of claim 4 wherein the bis- I azo dye has the followingformula: 5 H,N-C 0 10.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
US778294A 1967-12-13 1968-11-22 Photographic materials for the silver dye bleach process Expired - Lifetime US3615582A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEA0057670 1967-12-13
DE19671595504 DE1595504B2 (de) 1965-07-12 1967-12-13 Verfahren zur entfernung farbiger vanadium bestandteile aus kohlenwasserstoffloesungen von olefinpolymeren
DE19671597504 DE1597504A1 (de) 1967-12-13 1967-12-13 Photographische Materialien fuer das Silberfarbbleichverfahren

Publications (1)

Publication Number Publication Date
US3615582A true US3615582A (en) 1971-10-26

Family

ID=27180867

Family Applications (1)

Application Number Title Priority Date Filing Date
US778294A Expired - Lifetime US3615582A (en) 1967-12-13 1968-11-22 Photographic materials for the silver dye bleach process

Country Status (6)

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US (1) US3615582A (enrdf_load_html_response)
BE (1) BE725314A (enrdf_load_html_response)
CH (1) CH516813A (enrdf_load_html_response)
DE (1) DE1597504A1 (enrdf_load_html_response)
FR (1) FR1598427A (enrdf_load_html_response)
GB (1) GB1211928A (enrdf_load_html_response)

Also Published As

Publication number Publication date
BE725314A (enrdf_load_html_response) 1969-06-12
GB1211928A (en) 1970-11-11
FR1598427A (enrdf_load_html_response) 1970-07-06
CH516813A (de) 1971-12-15
DE1597504A1 (de) 1970-07-09

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