US2772164A - Photographic silver halide emulsions containing 1-thia-3, 5, 7-triazaindenes - Google Patents

Photographic silver halide emulsions containing 1-thia-3, 5, 7-triazaindenes Download PDF

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Publication number
US2772164A
US2772164A US479683A US47968355A US2772164A US 2772164 A US2772164 A US 2772164A US 479683 A US479683 A US 479683A US 47968355 A US47968355 A US 47968355A US 2772164 A US2772164 A US 2772164A
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United States
Prior art keywords
emulsions
silver halide
fog
photographic
thia
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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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US479683A
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English (en)
Inventor
Charles F H Allen
John J Sagura
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority to BE543978D priority Critical patent/BE543978A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US479683A priority patent/US2772164A/en
Priority to DEE11773A priority patent/DE1032668B/de
Priority to GB134/56A priority patent/GB789842A/en
Priority to FR1148762D priority patent/FR1148762A/fr
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Publication of US2772164A publication Critical patent/US2772164A/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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides

Definitions

  • This invention relates to fog inhibiting agents and stabilizers for photographic emulsions and to photographic emulsions containing them.
  • Fog depends both on the emulsion and the conditions of development; for a given emulsion it increases with the degree of development. With constant development conditions, it tends to increase with time, temperature and relative humidity of storage conditions; it is common practice to make accelerated tests of the stability of photographic emulsions by storage at increased temperature or humidity, or both. It is, of course, desirable to have emulsions as stable as possible under the condi tions of high temperature and humidity which may occur in tropical climates, for example. Fog usually appears over the whole area of the sensitive coating, but when severe, it frequently is non-uniform. Fog may also be caused by exposure to chemicals, for example, hydrogen sulfide and other reactive sulfur compounds, hydrogen peroxide vapor, and strongly reducing materials. While antifoggants and stabilizers may protect, to some extent, against such effects, it is normally understood that an antifoggant protects against spontaneous growth of fog during prolonged storage or storage at high temperatures and humidities, or during development to maximum contrast and speed, or both.
  • R represents an alkylmercapto group, such as methylmercapto, ethylmercapto, carboxyrnethylmercapto, carbomethoxymethylmercapto, etc. (e. g., an alkylmercapto group containing from 1 to 3 carbon atoms) or a monoalkylamino group, such as methylarnino, ethylamino, etc. (e. g., a monoalkylamino group containing from 1 to 2 carbon atoms), and R1 represents a hydrogen atom or a lower alkyl group, such as methyl, ethyl, etc. (e. g., an alkyl group of the formula CnH21L+1 wherein n is a positive integer of from 1 to 2)
  • R represents an alkylmercapto group, such as methylmercapto, ethylmercapto, carboxyrnethylmercapto, carbomethoxymethylmercapto, etc. (e.
  • an object of the present invention to provide a method for stabilizing photographic emulsions.
  • a further object is to provide a means for reducing the fog produced upon keeping of such emulsions which have been sensitized, especially emulsions stored under tropical or other adverse conditions.
  • a still further object is to provide a means for stabilizing the speed and contrast of sensitized photographic emulsions.
  • the antifoggant compounds represented by Formula I (or Ia) can be employed in emulsions which have been sensitized optically or chemically, or emulsions which have not been so sensitized. It is known that the effective sensitivity of photographic silver halide emulsions can be increased by adding to them derivatives of alkylene oxides, such as ethylene oxide polymers having molecular weights of 300 or more. The practical value of these compounds is severely limited by their tendency to increase fog on storage of the photographic film, especially storage at elevated temperatures and humidity. It has been found difiicult to control this by the antifoggants commonly available without using quantities of antifoggant which partly neutralize the speed increase obtained from the alkylene oxide derivatives.
  • the alkylene oxide polymers used to sensitize the emulsions can be of various types.
  • the alkylene oxides from which the polymers are derived contain from 2 to 4 carbon atoms, e. g., ethylene oxide, propylene oxide and butylene oxide.
  • the preparation of polymers from these compounds is described in Ellis, The Chemistry of Synthetic Resins (1935), pages 990 to 994.
  • These compounds are also referred to as polyalkylene glycols and their use as sensitizers for silver halide emulsions is described in U. S. Patents 2,423,549 and 2,441,389.
  • Ethylene oxide polymers have been found to be especially advantageous in practicing our invention.
  • alkylene oxides may also be used to sensitize the silver halide emulsions, e. g., condensation products of alkylene oxide with glycols, such as those having from 8 to 18 carbon atoms, as described in U. S. Patent 2,240,472 and British Patent 443,559, as well as condensation products of alkylene oxides with aliphatic alcohols, aliphatic acids and aliphatic amines, that is, polyalkylene ethers, esters and amides, the preparation of which is described in U. S. Patent 1,970,578, condensation products of alkylene oxides with phenols, also described in U. S. Patent 1,970,578, and condensation products of alkylene oxides with hexitol ring dehydration products, as described in U. S. Patent 2,400,532.
  • condensation products of alkylene oxide with glycols such as those having from 8 to 18 carbon atoms, as described in U. S. Patent 2,240,472 and British Patent 443,5
  • polyalkylene oxide or derivative of alkylene oxide should have a molecular weight of at least 300.
  • Condensation products of ethylene oxide with long chain alcohols should have a molecular weight of about 700; other derivatives may have a molecular weight of 1500 to 4000 or more.
  • the principal purpose of our invention is to provide a means for maintaining the sensitivity and fog of silver halide emulsions at or close to initial optimum values under conditions of high temperature or high humidity, or both.
  • the antifoggants of our invention are added to the emulsion at any stage during the process of manufacture prior to coating the emulsion,
  • the antifoggants can be added to the emulsion in solution in any convenient solvent not injurious to the emulsion, such as lower aliphatic alcohols.
  • alkylene oxide derivatives which can be used to sensitize the emulsions can be illustrated by the following specific examples, although our invention is in no Way limited to the use of these specific compounds.
  • the preparation of silver halide emulsions involves three separate operations: (1) the emulsification and digestion or ripening of the silver halide, (2) the freeing of'the emulsion from aqueous soluble salts usually by washing, (3) the second digestion or after-ripening to obtain increased sensitivity (Mees, The Theory of the Photographic Process, 1942, page 3).
  • the fog inhibiting agents can be added at any stage, preferably after the final digestion.
  • the photographic emulsions which we use are of the developing-out type and best results have been obtained with gelatino-silver bromoiodide emulsions. However, emulsions of varying halide content can be. used.
  • the emulsions can be chemically sensitized by any of the accepted procedures.
  • the emulsions can be digested with naturally active gelatin, or sulfur compounds may be added such as those described in Sheppard U. S. Patents 1,574,944 and U. S. 1,623,499, and Sheppard and Brigham U. S. Patent 2,410,689.
  • the emulsions can also be treated with salts of the noble metals such as ruthenium, rhodium, palladium, iridium and platinum, all of which belong to group VIII of the periodic table of elements and have an atomic weight greater than 100,
  • Representative compounds are ammonium chloropalladate, potassium chloroplatinate and sodium chloropalladite, which are used for sensitizing in amounts below that which produces any substantial fog inhibition, as described in Smith and Trivelli U. S. Patent 2,448,060, and as antifoggants in higher amounts, :as described in Trivelli and Smith U. S. Patents 2,566,245 and 2,566,263.
  • the emulsions can also be chemically sensitized with gold salts as described in Waller and Dodd U. S. Patent 2,399,083, or stabilized with gold salts as described in Damschroder U. S. Patent 2,597,856 and Yutzy and Leermakers U. S. Patent 2,597,915.
  • Suitable compounds are potassium chloroaurite, potassium aurithiocyanate, potassium chloroaurate, auric trichloride and 2-aurosulfobenzothia'zole methochloride.
  • the emulsions can also be chemically sensitized with reducing agents, such as stannous salts (Carroll U. S. Patent 2,487,850), polyamines such as diethylene triamine (Lowe and Jones U. S. Patent 2,518,698), polyamines such as spermine (Lowe and Allen U, S. Patent 2,521,925), or bis-(fi-aminoethyl) sulfide and its watersoluble salts (Lowe and Jones U. S. Patent 2,521,926).
  • reducing agents such as stannous salts (Carroll U. S. Patent 2,487,850), polyamines such as diethylene triamine (Lowe and Jones U. S. Patent 2,518,698), polyamines such as spermine (Lowe and Allen U, S. Patent 2,521,925), or bis-(fi-aminoethyl) sulfide and its watersoluble salts (Lowe and Jones U. S. Patent 2,521,926).
  • the emulsions can also be stabilized with the mercury compounds of Allen, Byers and Murray, U. S. application Serial No. 319,611 (now U. S. Patent 2,728,663,-issued December 27, 1955), Carroll and Murray U. S. application Serial No. 319,612 (now U S. Patent 2,728,664, issued December 27, 1955) and Leubner and Murray U. S. application Serial No. 319,613 (now U. S. Patent 2,728,665, issued December 27, 1955), all filed Novemnor 8, 1952.
  • antifoggants of our invention alone, or in combination with polyalkylene oxides or their derivatives, are provided.
  • optical sensitizing can affect stability of emulsions with respect to sensitivity, fog and latent image changes, the action of the antifoggants is not completely independent or" optical sensitizing or other emulsion variables.
  • unsensitized emulsions and emulsions sensitized with cyanine or merocyanine dyes, or both can be treated with the antifoggant compounds represented by Formula I (or Ia) above.
  • the quantity of antifoggant compound employed can be varied, depending upon the particular silver halide employed, degree of ripening, presence or absence of other emulsion addenda, etc. In general, the quantity of antifoggant can vary from about 0.005 to 0.25 gram per gram mole of silver halide in the emulsion. amounts can be used in combination with one or more of the chemical sensitizing and stabilizing agents listed above.
  • the stabilizing action afforded by the antifoggants'of our invention was determined by incubation of the emulsions for a period of one week at F. and at constant humidity. The speeds were-measured in terms of 30/E where E is the exposure required to produce a density of 0.2 above fog.
  • the antifogg-ants were added to a panchromatically sensitized, high speed silver bromiodide emulsion which had been chemically sensitized with a sulfur compound, such as described in Sheppard U. S'Patent 1,574,944 and potassium chloroaurate.
  • the emulsions were coated on a cellulose acetate support and the coatings exposed on an Eastman I(b) sensitometer and processed for five minutes in a developer having the following composition:
  • compound A is Z-carboxymethylmercapto 5 methyll-oxo-6-thiono-4,5,6,7-tetrahydro-1- thia-3,5,7-triazaindene
  • compound B is 5-methyl-2-methyl mercapto 4 oxo 6 thiono 4,5,6,7 tetrahydro-l-thia-
  • compound C is Z-methylamino- 4 oxo 6 thiono 4,5 ,6,7-tetrahydro-1-thia-3,5 ,7-triazaindene.
  • these antifoggants can be incorporated in a colloid layer, such as a gelatin overcoating layer or interlayer, in contact with the emulsion.
  • the fog-inhibiting agents which we have described can be used in various kinds of photographic emulsions. In addition to being useful in non-sensitized emulsions, they can also be used in orthochromatic, panchromatic, and X-ray emulsions. If used with sensitizing dyes they can be added to the emulsion before or after the dyes are added.
  • Various silver halides can be used as the lightsensitive material, including silver bromide, silver iodide, silver chloride, silver bromiodide, silver chlorobromide, silver chlorobromiodide, etc.
  • the antifoggants of our invention can be used in emulsions intended for color photography, for example, emulsions containing colorforming couplers, or emulsions to be developed by solutions containing couplers.
  • polyethylene oxide polymers used in the emulsions according to our invention can be prepared either by polymerizing ethylene oxide in the presence of aliphatic acids, aliphatic amines, or phenols, or by reacting the polymerized polyethylene oxide with aliphatic acids, acid chlorides, or esters, which produces similar products.
  • the dispersing agents can be gelatin, or other colloids, such as collodion, albumen, cellulose derivatives, synthetic resins, etc.
  • a photographic silver halide emulsion containing an antifoggant selected from those represented by the following general formula:
  • R represents a member selected from the group wherein R represents an alkylmercapto group containing from 1 to 3 carbon atoms and R1 represents an alkyl group of the formula C1LH21L+1 wherein n is a positive integer of from 1 to 2.
  • a photographic silver halide emulsion containing an antifoggant selected from those represented by the following general formula:
  • R represents a monoalkylamino group containing from 1 to 2 carbon atoms.

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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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US479683A 1955-01-03 1955-01-03 Photographic silver halide emulsions containing 1-thia-3, 5, 7-triazaindenes Expired - Lifetime US2772164A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE543978D BE543978A (en, 2012) 1955-01-03
US479683A US2772164A (en) 1955-01-03 1955-01-03 Photographic silver halide emulsions containing 1-thia-3, 5, 7-triazaindenes
DEE11773A DE1032668B (de) 1955-01-03 1956-01-02 Stabilisiertes photographisches Material
GB134/56A GB789842A (en) 1955-01-03 1956-01-03 Improvements in photographic silver halide emulsions
FR1148762D FR1148762A (fr) 1955-01-03 1956-01-03 Nouveaux produits photographiques contenant un inhibiteur de voile

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US479683A US2772164A (en) 1955-01-03 1955-01-03 Photographic silver halide emulsions containing 1-thia-3, 5, 7-triazaindenes

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US (1) US2772164A (en, 2012)
BE (1) BE543978A (en, 2012)
DE (1) DE1032668B (en, 2012)
FR (1) FR1148762A (en, 2012)
GB (1) GB789842A (en, 2012)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1095114B (de) * 1957-05-01 1960-12-15 Du Pont Stabilisierte wasserdurchlaessige photographische Halogensilberschicht
DE1096194B (de) * 1957-05-01 1960-12-29 Du Pont Stabilisierte photographische Halogensilberschicht
DE1155333B (de) * 1961-03-27 1963-10-03 Eastman Kodak Co Photographisches Material fuer die Herstellung von mehrfarbigen Bildern nach einem Farbstoffentwicklersubstanzen verwendenden Diffusionsuebertragungsverfahren und Durchfuehrung des Verfahrens
US3895948A (en) * 1971-12-28 1975-07-22 Fuji Photo Film Co Ltd Silver halide light-sensitive material containing a heterocyclic thione and a polyalkylene oxide
US4332888A (en) * 1978-11-20 1982-06-01 Polaroid Corporation Method for stabilizing and spectrally sensitizing photosensitive silver halide emulsion
JPS63163345A (ja) * 1986-12-25 1988-07-06 Fuji Photo Film Co Ltd 画像形成方法
US4888273A (en) * 1988-02-26 1989-12-19 Polaroid Corporation Stabilized tabular silver halide grain emulsions
US5478721A (en) * 1995-01-31 1995-12-26 Eastman Kodak Company Photographic elements containing emulsion stabilizers
WO2000009511A1 (en) * 1998-08-13 2000-02-24 Astrazeneca Ab Novel thiazolopyrimidine compounds
US20080214578A1 (en) * 2005-04-06 2008-09-04 Gunnar Nordvall Novel 5-Substituted 7-Amino-[1,3]Thiazolo[4,5-D]Pyrimidine Derivatives 793
US20090124637A1 (en) * 2005-04-06 2009-05-14 Astrazeneca Ab Novel 5,7-Disubstituted [1,3]Thiazolo[4,5-D]Pyrimidin-2(3H)-One Derivatives 794

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1962605C2 (de) * 1969-12-13 1983-09-08 Agfa-Gevaert Ag, 5090 Leverkusen Photographisches Aufzeichnungsmaterial
JPS6079348A (ja) * 1983-10-06 1985-05-07 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2566659A (en) * 1948-11-23 1951-09-04 Ilford Ltd Silver halide emulsions containing antifogging agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2444605A (en) * 1945-12-15 1948-07-06 Gen Aniline & Film Corp Stabilizers for photographic emulsions
US2444607A (en) * 1945-12-15 1948-07-06 Gen Aniline & Film Corp Stabilizers for photographic emulsions
US2566658A (en) * 1948-11-23 1951-09-04 Ilford Ltd Silver halide emulsions containing antifogging agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2566659A (en) * 1948-11-23 1951-09-04 Ilford Ltd Silver halide emulsions containing antifogging agents

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1095114B (de) * 1957-05-01 1960-12-15 Du Pont Stabilisierte wasserdurchlaessige photographische Halogensilberschicht
DE1096194B (de) * 1957-05-01 1960-12-29 Du Pont Stabilisierte photographische Halogensilberschicht
DE1155333B (de) * 1961-03-27 1963-10-03 Eastman Kodak Co Photographisches Material fuer die Herstellung von mehrfarbigen Bildern nach einem Farbstoffentwicklersubstanzen verwendenden Diffusionsuebertragungsverfahren und Durchfuehrung des Verfahrens
US3895948A (en) * 1971-12-28 1975-07-22 Fuji Photo Film Co Ltd Silver halide light-sensitive material containing a heterocyclic thione and a polyalkylene oxide
US4332888A (en) * 1978-11-20 1982-06-01 Polaroid Corporation Method for stabilizing and spectrally sensitizing photosensitive silver halide emulsion
JPS63163345A (ja) * 1986-12-25 1988-07-06 Fuji Photo Film Co Ltd 画像形成方法
US4888273A (en) * 1988-02-26 1989-12-19 Polaroid Corporation Stabilized tabular silver halide grain emulsions
US5478721A (en) * 1995-01-31 1995-12-26 Eastman Kodak Company Photographic elements containing emulsion stabilizers
WO2000009511A1 (en) * 1998-08-13 2000-02-24 Astrazeneca Ab Novel thiazolopyrimidine compounds
US6806273B1 (en) 1998-08-13 2004-10-19 Astrazeneca Ab Compounds
US20080214578A1 (en) * 2005-04-06 2008-09-04 Gunnar Nordvall Novel 5-Substituted 7-Amino-[1,3]Thiazolo[4,5-D]Pyrimidine Derivatives 793
US20090124637A1 (en) * 2005-04-06 2009-05-14 Astrazeneca Ab Novel 5,7-Disubstituted [1,3]Thiazolo[4,5-D]Pyrimidin-2(3H)-One Derivatives 794
US20110092519A1 (en) * 2005-04-06 2011-04-21 Astrazeneca Ab 5,7-disubstituted thiazolo[4,5-d]pyrimidines as chemokine inhibitors
US7947693B2 (en) 2005-04-06 2011-05-24 Astrazeneca Ab 5,7-disubstituted thiazolo[4,5-D]pyrimidines as chemokine inhibitors
US8088780B2 (en) 2005-04-06 2012-01-03 Astrazeneca Ab 5,7-disubstituted thiazolo[4,5-D]pyrimidines for the selective inhibition of chemokine receptors
US9440992B2 (en) 2005-04-06 2016-09-13 Acturum Life Science AB 5,7-disubstituted thiazolo[4,5-D]pyrimidines as chemokine inhibitors

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Publication number Publication date
FR1148762A (fr) 1957-12-13
DE1032668B (de) 1958-06-19
BE543978A (en, 2012)
GB789842A (en) 1958-01-29

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