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US3382071A - Silver halide photographic element containing spot or streak prevention compounds - Google Patents

Silver halide photographic element containing spot or streak prevention compounds Download PDF

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Publication number
US3382071A
US3382071A US430208A US43020865A US3382071A US 3382071 A US3382071 A US 3382071A US 430208 A US430208 A US 430208A US 43020865 A US43020865 A US 43020865A US 3382071 A US3382071 A US 3382071A
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US
United States
Prior art keywords
silver halide
gelatin
layer
compounds
photographic
Prior art date
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
Application number
US430208A
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English (en)
Inventor
Bodenstein Carl August
Vielhaber Hans
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Application granted granted Critical
Publication of US3382071A publication Critical patent/US3382071A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • G03C1/33—Spot-preventing agents
    • 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
    • Y10S430/139—Defect coating

Definitions

  • This invention relates to photography, and more particularly to photographic elements bearing silver halide emulsion layers which elements are free from spots or streaks.
  • the invention also relates to processes for preparing such elements.
  • particles of impurities which are most active chemically are light and heavy metals, their oxides and salts, and also, in particular, substances having acidic and basic reaction.
  • the appearance, size and intensity of the resulting defects depend chiefly on the time of action by the causative agent in the emulsion, the kind of emulsion, the rate of diffusion of ions of the causative agent, the length of storage time and also on the processing conditions used for the exposed material.
  • the photosensitive material substances which have a good sequestering capacity for metal ions, such for example as metaphosphates and polyphosphates or hydroxylated polyaminopolycarboxylic acids, e.g., derivatives of imino-, hydrazino-, ethylenediaminodiand ethylenediaminotriacetic acids.
  • metal ions such for example as metaphosphates and polyphosphates or hydroxylated polyaminopolycarboxylic acids, e.g., derivatives of imino-, hydrazino-, ethylenediaminodiand ethylenediaminotriacetic acids.
  • aldoximes and hydroxyketones such as hydroxyacetone, triose reductone, hydroxyacetophenone and the like.
  • a an R, R and R H, halogen, e.g., C1 or Br; alkyl of 14 carbons, e.g., ethyl, methyl, propyl and 'butyl, and substituted alkyl groups, acyl groups, e.g., acetyl and benzoyl; carboxyl, carboxyamide or carboxylic acid ester groups with an alkanol of 1-4 carbons, e.g., methyl and ethyl; where R, R and R may be alike or different.
  • R H, carboxyl, carboxyamide or carboxylic acid ester groups.
  • R H, alkyl or carbalkoxy groups of 1-4 carbons as listed above.
  • R and R together may also represent a doublebonded oxygen atom.
  • R H, alkyl of 14 carbons, as listed above, aralkyl
  • benzyl e.g., benzyl
  • aryl e.g., phenyl and naphthyl, substituted or not.
  • the compounds to be added in accordance with this invention are superior to those known in the art for such purposes. This superiority is presumably attributable to the fact that, in addition to high complex-forming capacity, they have a high buffering capacity and so are capable of counteracting pH changes due to the action of acidic or basic substances and thus of eliminating all defects which occur as a result of such local shifts in pH.
  • additives in accordance with this invention in conjunction with salts, suitably alkali metal salts, e.g., a sodium or potassium salt of ethylenediaminetetraacetic acid.
  • salts suitably alkali metal salts, e.g., a sodium or potassium salt of ethylenediaminetetraacetic acid.
  • the compounds provided in accordance with this invention in combination with salts of ethylen-ediamintetraacetic acid, have an antistatic eilect. It is known in the art that photosensitive photographic materials can acquire an electric charge due to friction effects in the manufacturing process. Aside from the fact that such electrically charged films or the like are subject to particularly severe dust deposits because they act as electrostatic precipitators, there is also the hazard that the photosensitive layer will be prematurely exposed to luminosity occurring during discharges. These drawbacks are eliminated by the substances provided in accordance with this invention when they are used in combination with salts of ethylenediaminetetraacetic acid.
  • An additional advantage of the additives according to this invention is that they are independent of pH within the pH range which is photochemically involved, so that their range of utility is in no wise restricted.
  • the additives in accordance with this invention are readily soluble in water and so are suitably incorporated with the photosensitive photographic layers in aqueous solution.
  • the designated compounds may be added to the photosensitive layer, but they are also effective in auxiliary layers, such as the barytes layer, adhesive layers, e.g., gelatin, etc. sublayers; interlayers, e.g., gelatin filter layers; or protective coatings or antihalation coatings. If the addition is made directly to the photosensitive silver halide emulsion layer, it is preferable to use 025-05 g. per kg. of emulsion.
  • the compounds to be used in accordance with this invention do not impair either the sensitivity or the gradation of the photosensitive photographic material and accordingly can be used both in photosensitive photographic films and in photographic papers. Because of their good compatibility with emulison additives they can be used in orthochromatically and in panchromatically sensitized emulsions, as well as in unsensitized emulsions, e.g., X-ray emulsions. It has been found that the compounds provided in accordance with this invention can also be added, with excellent results, to color photography emulsions containing coupling agents.
  • the compounds maltol and kojic acid which are particularly suited to the purposes of this invention, are commercial products, available on the market in adequate purity.
  • Example 1 There is applied to a cellulose triacetate film base a suspension of gelatin in organic solvents, containing 7 g. gelatin per liter, as an adhesive layer. A gelatin interlayer composed of a solution of gelatin in a water:methanol blend, containing 1 g. gelatin per liter, is coated over the adhesive layer.
  • test strips A and B were now prepared, which differed in that the adhesive layer solution for strip B contained maltol (Compound III in the table above) at 4 g./liter of the solution used in making the adhesive layer.
  • maltol Compound III in the table above
  • test strips A and B were exposed, developed in a customary metolzhydroquinone developer, fixed in an acidic fixative bath and then dried.
  • Strip A showed dark spots, while strip B was spotless.
  • Example 2 On the gelatin interlayer of a material constructed as in Example 1, after contaminating it with dust sweepings from the production room, a highly sensitive panchromatic neutral silver bromideziodide (5% AgI) emulsion suitable for portrait film was coated. It contained 10% gelatin and 0.33 mol/kg. of silver halide. One of the customary gelatin protective coatings was then applied to the photosensitive layer. This material served as test specimen A. For the comparison specimen B, the same material was employed, with the difference that its gelatin interlayer contained pyrocomene amine acid (Compound II in the table above) at 1.5 g./liter of the slution employed in making the protective coating.
  • pyrocomene amine acid Compound II in the table above
  • Strip A showed light and dark spots, while strip B was completely flawless.
  • Example 3 The gelatin interlayer, still wet, of a photographic material prepared as in Example 1, is contaminated with finely divided rust and other corrosion dust from the coating machinery (specimen A). For comparison the same material is employed, with the difference that its photosensitive emulsion contained kojic acid (Compound V in the table above) at 0.5 g./liter of emulsion. After drying, the two strips were exposed, developed, fixed and dried. Strip A shows dark spots, while strip B is completely flawless.
  • kojic acid Compound V in the table above
  • Example 4 The gelatin interlayer, still wet, of a photosensitive photographic material made according to Example 2 is contaminated with dust from powdered dye-containing antihalation layers, specimen A.
  • control specimen B the same material is employed, with the difference that its protective coating contains S-hydroxy-pyrone-(Z) (Compound I of the table above) at 5 g./ liter of the solution employed in making the protective coating.
  • Strip A shows white spots while strip B is completely flawless.
  • the invention is not limited to incorporating the novel compounds shown above in photographic elements having gelatino-silver halide emulsions of the type given in the above examples. It may be applied to other simple and mixed silver halide emulsions.
  • the emulsions can contain binding agents other than geltain or mixtures of gelatin and such binding agents. Suitable binding agents include polyvinyl alcohol and acetals thereof, polyvinyl pyrrolidone, polyvinvyl lactams, cellulose esters, dextrin These same water-permeable macromolecular organic and dextran, the latter two being mixed with gelatin.
  • protective colloids and mixtures can be used for the subl-ayers, filter layers or protective layers.
  • the emulsions can contain color formers and other emulsion adjuvants including non-optical sensitizers such as sulfur sensitizers containing labile sulfur, e.g., allyl isothiocyanate allyl diethyl thiourea, phenyl isothiocyanate and sodium thiosulfate, the polyoxyalkylene ethers in Blake et al., US. 2,400,532 and the polyglycols disclosed in Blake et al., U.S. 2,423,549.
  • nonoptical sensitizers such as amines as taught by Stand et al., US. 1,925,508 and metal salts as taught by Baldsiefen et al., US.
  • Antifoggants e.g., benzotriazole and triazaindenes
  • hardeners i.e., chrome alum, formaldehyde, etc.
  • the photographic emulsion or adhesive layer may be coated on any suitable support such as paper or films composed of cellulose esters, e.g., cellulose triacetate, cellulose acetate/butyrate, superpolymers, e.g., poly(vinyl chloride covinyl acetate) polyvinyl acetals, e.g., formals, acetals; polystyrene; polyamides, e.g., polyhexamethylene adipamide, and polyesters, e.g., polyethylene terephthalate, polyethylene terephthalate/isophthalate; esters formed by condensing terephthalic acid and dimethyl terephthalate with propylene glycol, tetramethylene glycol or cyclohexane-1,4-dimethanol (hexahydro-p-xylene alcohol).
  • cellulose esters e.g., cellulose triacetate, cellulose acetate/butyrate
  • a photographic element comprising a support bearing at least one silver halide emulsion layer, said element being characterized in that it has at least one waterpermeable organic colloid layer containing one or more compounds having the general formula:
  • x is a member selected from the group consisting of O- and and wherein R, R and R separately are each members selected from the group consisting of H, Cl, Br, alkyl of 1-4 carbons, acyl, carboxyl, carboxamide and carboxyalkyl of 2-5 carbons, and R and R when together constitute the atoms necessary to form an aromatic ring;
  • R is a member selected from the group consisting of H, carboxyl, carboxamide and carboxyalkyl of 2-5 carbons;
  • R is a member selected from the group consisting of H, alkyl of 1-4 carbons and carbalkoxy of 14 carbons, and R and R together constitute doubly bonded oxygen atom; and
  • R is a member selected from the group consisting of H, alkyl of 1-4 carbon atoms, aralkyl and aryl.
  • An element according to claim 1 having at least one gelatino-silver halide photographic emulsion layer.
  • the layer containing the compound is a gelatin layer contiguous with a gelatin-silver halide photographic emulsion layer.
  • a photographic element according to claim I having at least one water-permeable organic colloid layer containing kojic acid and an alkali metal salt of ethylenediaminetetraacetic acid.
  • the layer containing the compound is a gelatin layer contiguous with a gelatino-silver halide photographic emulsion layer.
  • a photographic element according to claim 1 having at least one water-permeable organic colloid layer containing maltol.
  • a photographic element according to claim 1 having at least one water-permeable organic colloid layer containing maltol and an alkali metal salt of ethylene diaminetetraacetic acid.
  • the layer containing the compound is a gelatin layer contigu ous with a gelatino-silver halide photographic emulsion layer.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US430208A 1964-06-24 1965-02-03 Silver halide photographic element containing spot or streak prevention compounds Expired - Lifetime US3382071A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA46406A DE1198200B (de) 1964-06-24 1964-06-24 Lichtempfindliches photographisches Material

Publications (1)

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US3382071A true US3382071A (en) 1968-05-07

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US (1) US3382071A (xx)
BE (1) BE665814A (xx)
DE (1) DE1198200B (xx)
GB (1) GB1090244A (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3876427A (en) * 1972-02-08 1975-04-08 Fuji Photo Film Co Ltd Developer for photographic materials used in the graphic arts
US4340665A (en) * 1981-03-04 1982-07-20 E. I. Du Pont De Nemours And Company Silver halide film

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69636024T2 (de) * 1995-08-23 2006-08-31 Fuji Photo Film Co., Ltd., Minami-Ashigara Verfahren zur Verarbeitung lichtempfindlichen Silberhalogenidfarbmaterials

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2460188A (en) * 1945-05-02 1949-01-25 Commercial Solvents Corp Fungicidal compositions
US2845349A (en) * 1955-09-07 1958-07-29 Powers Chemco Inc Photographic developers
US3130204A (en) * 1962-02-07 1964-04-21 Pfizer & Co C Preparation of gamma-pyrones
US3138556A (en) * 1961-09-05 1964-06-23 Purex Corp Ltd Coating remover composition
US3186853A (en) * 1964-09-03 1965-06-01 Baltimore Spice Co Method of processing meat
US3305363A (en) * 1962-11-13 1967-02-21 Eastman Kodak Co Photographic development promoters
US3310405A (en) * 1962-08-29 1967-03-21 Agfa Ag Spot prevention in light-sensitive silver halide emulsion layers

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2460188A (en) * 1945-05-02 1949-01-25 Commercial Solvents Corp Fungicidal compositions
US2845349A (en) * 1955-09-07 1958-07-29 Powers Chemco Inc Photographic developers
US3138556A (en) * 1961-09-05 1964-06-23 Purex Corp Ltd Coating remover composition
US3130204A (en) * 1962-02-07 1964-04-21 Pfizer & Co C Preparation of gamma-pyrones
US3310405A (en) * 1962-08-29 1967-03-21 Agfa Ag Spot prevention in light-sensitive silver halide emulsion layers
US3305363A (en) * 1962-11-13 1967-02-21 Eastman Kodak Co Photographic development promoters
US3186853A (en) * 1964-09-03 1965-06-01 Baltimore Spice Co Method of processing meat

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3876427A (en) * 1972-02-08 1975-04-08 Fuji Photo Film Co Ltd Developer for photographic materials used in the graphic arts
US4340665A (en) * 1981-03-04 1982-07-20 E. I. Du Pont De Nemours And Company Silver halide film

Also Published As

Publication number Publication date
BE665814A (xx) 1965-12-23
GB1090244A (en) 1967-11-08
DE1198200B (de) 1965-08-05

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