US2860979A - Azo dyes as filters in color photography - Google Patents

Azo dyes as filters in color photography Download PDF

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Publication number
US2860979A
US2860979A US503877A US50387755A US2860979A US 2860979 A US2860979 A US 2860979A US 503877 A US503877 A US 503877A US 50387755 A US50387755 A US 50387755A US 2860979 A US2860979 A US 2860979A
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United States
Prior art keywords
light
group
photographic
dyes
screening
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US503877A
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English (en)
Inventor
James M Straley
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE547136D priority Critical patent/BE547136A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US503877A priority patent/US2860979A/en
Priority to FR1152693D priority patent/FR1152693A/fr
Priority to GB12926/56A priority patent/GB820738A/en
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    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/40—Dyestuffs not covered by the groups G03C1/08 - G03C1/38 or G03C1/42
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • 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
    • G03C1/831—Azo 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
    • G03C11/00—Auxiliary processes in photography
    • G03C11/08—Varnishing, e.g. application of protective layers on finished photographic prints
    • G03C11/10—Varnishing, e.g. application of protective layers on finished photographic prints for protection from ultraviolet light

Definitions

  • the present invention relates to improved photographic elements, and more particularly, to photographic elements having light-screening substances therein.
  • Such a light-screening substance can be in a layer overlying a light-sensitive emulsion or two or more such light-sensitive emulsions, or it can be incorporated in the light-sensitive emulsion layer itself for the purpose of modifying a light record in such emulsion, or protecting an underlying light-sensitive emulsion or emulsions from the action of light of wave-length absorbed by such light-screening substances.
  • such lightscreening substances can be in a layer not containing a light-sensitive substance, but arranged between two lightsensitive emulsions, or such light-screening substances can be in a layer serving as a backing on an element having one or more light-sensitive emulsions for the purpose of reducing halation.
  • such light-screening substances are required in layers arranged between differentially-colored sensitized emulsions, e. g., to protect the red and green sensitized emulsions from the action of blue light, or in backings forming the so-called anti-halation layers on either side of a transparent support carrying the lightsensitive emulsion or emulsions.
  • the photographic element contains differentially-colored sensitized emulsions (or color-sensitized emulsions)
  • Such light-screening substances which do not undergo substantial diflusion from the layers or coatings in which they are incorporated, either during the manufacture of the photographic element or on keeping 'it in a photographic processing solution, are especially useful.
  • Such light-screening substances should be easily removed or made ineffective by one of the processing solutions customarily employed in photographic treatments, e. g., a photographic developing bath, fixing bath, or a silver-oxidizing (including silver-removing) bath.
  • Such removal or rendering ineffective is particularly important when making color photographs using several differentially color-sensitized emulsions containing the usual silver halide salts.
  • differentially color-sensitized emulsions must be processed to diiferent colors and to facilitate diflerential colorprocessing, methods involving selectiveexposure of light-sensitive images in the layers can be employed.
  • Such selective re-exposure e. g., of silver halide remaining undeveloped in development of the latent images formed in silver halide emulsion layers is often facilitated, if the light-screening substance ized or removed during treatment in one of the processing granted August 16, 1938.
  • the instant invention relates to the use of a new type of light-screening dye which is easily removed during the photographic processing customarily employed.
  • the dyes of my invention form stable filter coatings and cause little or no'desensitizing in photographic emulsions with which they come in contact.
  • H 5 RN N oH wherein R represents an aryl group, such as phenyl,
  • Another group of dyes embraced by Formula H above which can advantageously be employed in practicing my invention are those dyes represented by which was present during the original exposure is decolorthe following general formula:
  • R and R each represents a hydrogen atom, a
  • halogen atom e. g., chlorine, bromine, etc.
  • a nitro group e. g., a cyano group, a sulfonamido group, a hydroxyl group, an alkoxyl group (e. g., methoxyl, ethoxyl, etc.), an aryloxyl group (e. g., phenoxyl, methylphenoxyl, etc.), an aryl group (e. g., phenyl, 0-, mand p-tolyl, etc.),
  • alkoxyl group e. g., methoxyl, ethoxyl, etc.
  • an aryloxyl group e. g., phenoxyl, methylphenoxyl, etc.
  • an aryl group e. g., phenyl, 0-, mand p-tolyl, etc.
  • alkyl group e. g., methyl, ethyl, n-propyl, etc.
  • Patented Nov. 18 19 58v wherein R and R each have the values given above. While the mixture can be heated somewhat to facilitate the desired reaction, it is generally not necessary to do so, and room temperatures, or temperatures below room temperature, can advantageously be employed.
  • the diazonium salts of the amines represented by Formula IV above can be prepared in the known manner, from a mixture of sodium nitrite and hydrochloric acid. The method of preparing compounds selected from those represented by Formulas II and III above is further described in Jour. Am. Chem. Soc., vol. 77 (1955), pages 403- 405.
  • the aromatic amines represented by Formula IV above required for the preparation of the light-screening dyes of my invention can be prepared as described in Sprung U. S. Patent 2,629,658, issued February 24, 1953. Many of these amines are old substances and having been described elsewhere.
  • the light-screening dyes of my invention are water-soluble, they can be incorporated in the photographic layer by simply preparing stock solutions of the dye and adding these photographic solutions to an aqueous solution or suspension of the conventional water-permeable colloids employed in photographic coatings such as gelatin, polyvinyl alcohol, starch, agar-agar, gum arabic, hydrolyzed cellulose acetate, hydroxymethyl cellulose, etc.
  • the filter dye is not soluble in water, it can be dissolved in one of the usual organic solvents, such as pyridine, ethanol, etc., and added to the waterpermeable colloid in this condition.
  • Example 1 Five g. of sulfanilic acid were dissolved in 25 cc. of water containing 2.5 g. KOH. The solution was cooled to 5 C. and a solution of 2.0 g. NaNO in 20 cc. of water added, followed by addition beneath the surface of a chilled solution of 4 cc. of water and 8 cc. of concen trated HCl at 57 C. After addition, the solid diazonium salt was filtered off and added to a solution of 3.65 g. of B-methylglutaconic anhydride in 25 cc. of propionicacetic acids (1:5), hereinafter referred to as 1:5 acid.
  • the mineral acid was neutralized to Congo red with ammonium acetate and stirred without cooling for 2.5 hours. The mix was then drowned in 200 cc. of saturated salt solution. The dye was isolated by filtration, washing with ice water and drying at 60 C. The yield was 8 g. of a bright yellow solid. This product can be boiled in water without alteration. However, upon solution in 2% Na C solution and warming to 40 C. the color was permanently discharged in about 15 seconds.
  • Example 2 1.81 g. of S-aminoisophthalic acid were dissolved in 10 cc. of water and 3.3 cc. of concentrated HCl. After cooling to C., a solution of 0.72 g. NaNO in 5 cc. of water was added at 5-6 C. After 30 minutes at this temperature, the diazonium salt was added to a solution of 1.26 g. of B-methylglutaconic anhydride and 1.0 g. of sodium acetate (anhydrous) in 50 cc. of water and 25 g. of ice. After 15 minutes the dye was filtered off, washed with HO], and dried at room temperature. The yield was 2 g. of a substance behaving almost precisely as the product of Example 1.
  • Example 3 2.7 g. of 2-amino-5-toluenesulfonic acid were dissolved in 12.5 cc. of water and 1.25 g. KOH. After cooling to 5 C., a solution of 1.0 g. of NaNO: in 5 cc. of water was added. At 5 C. a solution of 2 cc. H 0 and 4 cc. concentrated HCl was added in about 10 minutes and the solid diazonium salt filtered ofi. The filter cake was added to a solution of 1.83 g. B-methylglutaconic anhydride in cc. of 1:5 acid at 5 C., neutralized to Congo red with ammonium acetate and stirred 2 hours without cooling. After isolation as in Example 1, there were obtained 4.9 g. yellow product, which behaved towards alkali precisely as did the product of Example 1.
  • Example 4 The product obtained by coupling p-nitroaniline to methylglutaconic anhydride was dissolved in tricresyl phosphate. The solution was dispersed in a gelatin solution and used as in Example 4. v
  • filter dyes selected from those represented by Formulas II (or I) and HI above can be incorporated in photographic elements.
  • the light-screening dyes of my invention are discharged during photographic development. In those cases where this does not occur, the dye can be discharged by simply bathing the photographic element in a dilute alkaline solution for a few seconds as mentioned above. This treatment does not harm the photographic element in any way.
  • Figure 1 is a sectional view of a multi-layer film in which the support 10 of any suitable material, such as cellulose acetate, paper, metal, polyvinyl acetal film, superpolyamide film, etc. is coated with gelatino-silver halide emulsion layers 11, 12 and 13, sensitive to the red, green, and blue regions of the spectrum, respectively.
  • the layer 14 is a gelatin filter layer containing one of the filter dyes of my invention, such as that represented by Example 3 above.
  • Figure 2 illustrates another modification of my invention in which the support 10 is coated on one side with emulsion layer 16 and on the opposite side with gelatin layer 17 containing one of the filter dyes of my invention, such as the dye set forth in Example 3.
  • the light-sensitive salts which can be employed in my invention comprise the ordinary gelatino-silver-halide, such as gelatino-silver-chloride, gelatino-silver-bromide, gelatino-silver-chlorobromide, gelatino-silver-bromiodide, gelatinosilver-chlorobromiodide, etc.
  • the light-sensitive a 6 layers can contain the usual sensitizing dyes, such as cyanine, merocyanine, etc., dyes.
  • the light-screening filters of my invention can be incorporated in one of the light-sensitive layers. The lightscreening filter will then be easily removed during the usual photographic processing.
  • a light-sensitive photographic element comprising light-sensitive silver halide and a light-absorbing, waterpermeable colloid layer containing a dye represented by the following general formula:
  • R represents an aryl group
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye selected from those represented by the following general formula:
  • R represents a monocyclic aromatic group of the benzene series.
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye selected from those represented by the following general formula:
  • R represents a monocyclic aromatic group of the benzene series having substituted thereon a radical selected from the group consisting of a carboxyl radical, a sulfo radical, and alkali metal salts of said radicals.
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye selected from those represented by the following general formula:
  • R and R each represents a member selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonamido group, a hydroxyl group, an alkoxyl group, an aryloxyl group, an aryl group, an alkyl group, an alkanesulfonyl group, an arenesulfonyl group, a carbalkoxyl group, a carbamido group, and a guanidino salt of a sulfo group.
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye represented by the following formula:
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye represented by the following formula:
  • a photographic element comprising at least one light-sensitive silver halide emulsion layer and a lightabsorbing, water-permeable colloid layer containing a dye represented by the following formula:

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US503877A 1955-04-26 1955-04-26 Azo dyes as filters in color photography Expired - Lifetime US2860979A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE547136D BE547136A (ja) 1955-04-26
US503877A US2860979A (en) 1955-04-26 1955-04-26 Azo dyes as filters in color photography
FR1152693D FR1152693A (fr) 1955-04-26 1956-04-25 Nouveau type de colorants et produits photographiques contenant ces colorants
GB12926/56A GB820738A (en) 1955-04-26 1956-04-26 Photographic elements containing light-screening substances

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US503877A US2860979A (en) 1955-04-26 1955-04-26 Azo dyes as filters in color photography

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BE (1) BE547136A (ja)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291602A (en) * 1961-08-09 1966-12-13 Agfa Ag Masking process for the production of photographic images
US5455150A (en) * 1993-06-10 1995-10-03 Eastman Kodak Company Color photographic negative elements with enhanced printer compatibility

Citations (5)

* 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
US2432419A (en) * 1944-04-19 1947-12-09 Gen Aniline & Film Corp Azo hydroxy aza indolizines
US2461485A (en) * 1945-06-21 1949-02-08 Gen Aniline & Film Corp Xanthylium dye salts as filter and antihalation dyes in photographic materials
US2464785A (en) * 1947-11-18 1949-03-22 Gen Aniline & Film Corp Monazo compounds containing a thiazolone cyanine dye component
US2704711A (en) * 1952-06-28 1955-03-22 Eastman Kodak Co Photographic color correction

Patent Citations (5)

* 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
US2432419A (en) * 1944-04-19 1947-12-09 Gen Aniline & Film Corp Azo hydroxy aza indolizines
US2461485A (en) * 1945-06-21 1949-02-08 Gen Aniline & Film Corp Xanthylium dye salts as filter and antihalation dyes in photographic materials
US2464785A (en) * 1947-11-18 1949-03-22 Gen Aniline & Film Corp Monazo compounds containing a thiazolone cyanine dye component
US2704711A (en) * 1952-06-28 1955-03-22 Eastman Kodak Co Photographic color correction

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291602A (en) * 1961-08-09 1966-12-13 Agfa Ag Masking process for the production of photographic images
US5455150A (en) * 1993-06-10 1995-10-03 Eastman Kodak Company Color photographic negative elements with enhanced printer compatibility

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Publication number Publication date
BE547136A (ja)
GB820738A (en) 1959-09-23
FR1152693A (fr) 1958-02-21

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