US2751297A - Photographic emulsion layer containing a 3-pyrazolidone - Google Patents

Photographic emulsion layer containing a 3-pyrazolidone Download PDF

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Publication number
US2751297A
US2751297A US371948A US37194853A US2751297A US 2751297 A US2751297 A US 2751297A US 371948 A US371948 A US 371948A US 37194853 A US37194853 A US 37194853A US 2751297 A US2751297 A US 2751297A
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United States
Prior art keywords
pyrazolidone
emulsion
silver halide
emulsion layer
compounds
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
US371948A
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English (en)
Inventor
Glay M Hood
Paul R Crookshank
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Eastman Kodak Co
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Eastman Kodak 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
Priority to US372168A priority Critical patent/US2691589A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to BE530883D priority patent/BE530883A/xx
Priority to US371948A priority patent/US2751297A/en
Priority to US372166A priority patent/US2688548A/en
Priority to FR1109575D priority patent/FR1109575A/fr
Priority to FR1106144D priority patent/FR1106144A/fr
Priority to FR1106813D priority patent/FR1106813A/fr
Priority to GB22505/54A priority patent/GB767699A/en
Priority to BE530887D priority patent/BE530887A/xx
Priority to GB22510/54A priority patent/GB767704A/en
Application granted granted Critical
Publication of US2751297A publication Critical patent/US2751297A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • 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
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/30—Developers
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/264—Supplying of photographic processing chemicals; Preparation or packaging thereof
    • G03C5/265—Supplying of photographic processing chemicals; Preparation or packaging thereof of powders, granulates, tablets

Definitions

  • FIG. 1 The accompanying drawings show in; greatly enlarged cross-sectional view the appearance of a representative photographic element contemplated by our invention.
  • layer represents a support such as paper, cellulose ester, etc.
  • layer lit the emulsion layer of the invention containing a mixture of silver halide and a 3-pyrazolidone compound.
  • the 3-pyrazolidone compounds employed inthe emulsions have thegeneral structure in which the various R groups repre sent substituents such as hydrogen, alkyl heterocyclicor aryl* groups, for-example, R can be benzothiazolyl or an -aryl;fgroup--of the benzene or naphthalene series, substituted or not;however, R cannot be a hydrogen atom inasmuch as 3-pyrazolidone compounds containing no substituent other than hydrogen in the l-position of the nucleus, such as 3.-pyraz- 1.
  • the '3-pyrazolidone compounds can be used in silver halide-emulsionsifor the purposes of the invention with gratifyingresults in a rather wide range of concentration.
  • Usefullresults can be obtained, for example, with from about 0.2 to 2.0 grams of the B-pyrazolidone compound per mol of silver nitrate used in making the emulsion and converted to silverhalide.
  • B-pyrazolidone compound per mol of silver nitrate used in making the emulsion and converted to silverhalide.
  • the particular silver halide infthe emulsioni is not especially critical nor is the particular'method used for preparing the emulsion.
  • oneior more of the.3.-pyrazolidone compounds cantbe added toemulsions containing mixtures of silver bromide, silver chloride and silver iodide such as present in emulsion' of well known types.
  • the 3-pyrazolidones are-particularly useful in conjunction with bromoiodide emulsions which normally develop slowly andinemulsions which normally require a short first development as in bleach redevelopment reversal processes.
  • the 3-pyrazolidone compounds are added in water solution to the emulsions at any stage in their preparation but are conveniently added after the final digestion'and just before coating. .As will be apparent, the emulsions may contain the usual addenda including .antifoggants, spreading agents, coupler compounds, etc.
  • Such emulsions zare adaptable to use in forming single as well as multi-layer films useful in color photography which customarily include two or more emulsion layers on -a support :sensitized to diiferent regions of the'visiblespectrum and which may or may not contain coupler compounds.
  • EXAMPLE 1 Samples of a finished washed bromo-iodide emulsion were provided. To the respective samples of melted emulsion were added aqueous solutions of the 3-pyrazolidone compounds indicated in the fololwing table. The samples were coated successively on a paper stock and dried. The samples were then given continuous wedge exposures and developed for 20 to 45 seconds both when the samples were fresh and after 3-day incubation at 120 F. and 60 percent relative humidity, development being carried out in a conventional Elon-hydroquinone developer. Sensitometric evaluation of the developed samples produced the data tabulated in the following table.
  • the bar gamma values in the table are a measure of the contrast of the developed samples and a description of the determination of this value is given in the American Standards Association Bulletin entitled Sensitometry and Grading of Photographic Papers, January 8, 1953.
  • the development acceleration effect of using the B-pyrazolidone compounds in the emulsions should be made between samples detioned previously, it appears essential that the 3-pyrazolidone compounds contain a substituent other than hydrogen in the l-position of the nucleus since compounds such as 3-pyrazolidone do not produce the desired effect 5 when incorporated into silver halide emulsion layers.
  • a light-sensitive photographic emulsion comprising a mixture of unexposed silver halide and a-3-pyrazolidone having the following general structure veloped for 20 seconds and the stabilizing eifect of the E2 compounds should be evaluated on the basis of the samples developed for 45 seconds. It will be apparent from 1 H the data that the 3-pyrazolidone compounds materially increase the contrast of the emulsion and stabilize the T emulsion against contrast loss on aging.
  • EXAMPLE 2 To a sample of a normally slow-developing brornoiodide emulsion used in reversal processes was added 8.77 milligrams of 1-phenyl-3-pyrazolidone per mol of silver nitrate used in making the emulsion and converted to silver halide. The emulsion was coated as usual on a paper base, exposed, developed in a caustic hydroqui none developer and evaluated sensitometrically.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and l-phenyl- 4,4-dimethyl-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and a l-tolyl- 4,4-dialkyl-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and .l-ptolyl-4,4-dimethyl-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in, the
  • a light-sensitive photographic emulsion compriswherein R represents a mononuclear aryl group of the benzene series, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and 1-phenyl- 3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and a 1- tolyl-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and l-ptolyl-S-pyrazolidine, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and a l-whydroxyalkylphenyl-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic emulsion layer comprising a mixture of unexposed silver halide and 1(p-,8- hydroxy-ethylphenyl)-3-pyrazolidone, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
  • a light-sensitive photographic element comprising a support, an unexposed silver halide emulsion layer, and a hydrophilic colloid layer adjacent to said emulsion layer containing a 3-pyrazolidone having the following general structure wherein R represents a member of the group consisting of heterocyclic groups and aryl groups of the benzene and naphthalene series and R1, R2, R3 and R4 each represent a member of the group consisting of a hydrogen atom, a mononuclear aryl group of the benzene series, and an alkyl group containing from 1 to 4 carbon atoms, in a small amount not in excess of about 2 grams per mol of silver halide in the emulsion.
US371948A 1953-08-03 1953-08-03 Photographic emulsion layer containing a 3-pyrazolidone Expired - Lifetime US2751297A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BE530883D BE530883A (fr) 1953-08-03 1953-08-03
US371948A US2751297A (en) 1953-08-03 1953-08-03 Photographic emulsion layer containing a 3-pyrazolidone
US372166A US2688548A (en) 1953-08-03 1953-08-03 Photographic developer composition
US372168A US2691589A (en) 1953-08-03 1953-08-03 Photographic developer compositions
FR1109575D FR1109575A (fr) 1953-08-03 1954-08-02 Révélateur photographique de nouvelle composition
FR1106144D FR1106144A (fr) 1953-08-03 1954-08-02 Nouveau révélateur photographique
FR1106813D FR1106813A (fr) 1953-08-03 1954-08-02 Nouveau produit photosensible
GB22505/54A GB767699A (en) 1953-08-03 1954-08-03 Improvements in photographic developer compositions
BE530887D BE530887A (fr) 1953-08-03 1954-08-03
GB22510/54A GB767704A (en) 1953-08-03 1954-08-03 Improvements in photographic emulsions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US371948A US2751297A (en) 1953-08-03 1953-08-03 Photographic emulsion layer containing a 3-pyrazolidone
US372168A US2691589A (en) 1953-08-03 1953-08-03 Photographic developer compositions

Publications (1)

Publication Number Publication Date
US2751297A true US2751297A (en) 1956-06-19

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Family Applications (3)

Application Number Title Priority Date Filing Date
US372168A Expired - Lifetime US2691589A (en) 1953-08-03 1953-08-03 Photographic developer compositions
US372166A Expired - Lifetime US2688548A (en) 1953-08-03 1953-08-03 Photographic developer composition
US371948A Expired - Lifetime US2751297A (en) 1953-08-03 1953-08-03 Photographic emulsion layer containing a 3-pyrazolidone

Family Applications Before (2)

Application Number Title Priority Date Filing Date
US372168A Expired - Lifetime US2691589A (en) 1953-08-03 1953-08-03 Photographic developer compositions
US372166A Expired - Lifetime US2688548A (en) 1953-08-03 1953-08-03 Photographic developer composition

Country Status (4)

Country Link
US (3) US2691589A (fr)
BE (2) BE530883A (fr)
FR (3) FR1106144A (fr)
GB (2) GB767704A (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257205A (en) * 1960-10-12 1966-06-21 Gevaert Photo Prod Nv Method for heat development
US3278307A (en) * 1961-11-21 1966-10-11 Eastman Kodak Co Photographic process for producing prints stabilized against print-out
US3300307A (en) * 1963-01-18 1967-01-24 Eastman Kodak Co Photographic developer composition
US3335007A (en) * 1962-06-15 1967-08-08 Gevaert Photo Prod Nv Silver halide diffusion transfer process
US3632340A (en) * 1968-09-09 1972-01-04 Eastman Kodak Co Cored direct positive silver halide emulsion developed with polyhydroxybenzene
US4734358A (en) * 1984-10-05 1988-03-29 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
USH1119H (en) 1990-01-19 1992-12-01 Fuji Photo Film Co., Ltd. Direct positive photographic material
USH1242H (en) 1990-03-03 1993-10-05 Konica Corporation Silver halide photographic light-sensitive material
US5447826A (en) * 1991-08-16 1995-09-05 Agfa-Gevaert, N.V. Photographic silver halide material

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875048A (en) * 1957-09-30 1959-02-24 Eastman Kodak Co Combined photographic developing and stabilizing solution
US3330661A (en) * 1962-11-13 1967-07-11 Eastman Kodak Co Photographic development precursors
US3649280A (en) * 1968-11-29 1972-03-14 Eastman Kodak Co Photographic elements and compositions
US4038080A (en) * 1972-09-21 1977-07-26 Minnesota Mining And Manufacturing Company Fix and bleach-fix bath desilvering
US3942985A (en) * 1973-08-24 1976-03-09 Minnesota Mining And Manufacturing Company High contrast, rapid access, air stable, regenerable iron chelate developer solutions
US4365085A (en) * 1978-02-27 1982-12-21 Polaroid Corporation Bicyclic reductone developing agents
US4154611A (en) * 1978-02-27 1979-05-15 Polaroid Corporation Bicyclic reductone developing agents
CA1267557A (fr) 1985-05-16 1990-04-10 Shigeharu Koboshi Systeme revelateur pour materiau photographique polychrome photosensible a teneur d'halogenure d'argent
EP0449340B1 (fr) * 1990-02-26 1996-10-16 Agfa-Gevaert N.V. Stabilisateurs photographiques ayant un groupe développateur
IT1240677B (it) * 1990-04-24 1993-12-17 Minnesota Mining And Manufacturing Company Composizione di sviluppo fotografico a colori e metodo per trattare unelemento fotografico a colori agli alogenuri d'argento
US5147767A (en) * 1991-04-10 1992-09-15 Knapp Audenried W Gluconic acid-based developer composition
EP0528480B1 (fr) * 1991-08-16 1997-11-19 Agfa-Gevaert N.V. Un matériau photographique à l'halogénure d'argent
US5384232A (en) * 1991-12-02 1995-01-24 E. I. Du Pont De Nemours And Company Process for rapid access development of silver halide films using pyridinium as development accelerators
US5236816A (en) * 1992-04-10 1993-08-17 Eastman Kodak Company Photographic developing solution and use thereof in the high contrast development of nucleated photographic elements
US5264323A (en) * 1992-04-10 1993-11-23 Eastman Kodak Company Photographic developing solution and use thereof in the high contrast development of nucleated photographic elements
US5384233A (en) * 1992-06-15 1995-01-24 Konica Corporation Chemicals kit including a container formed of multilayer film, for processing photographic light-sensitive materials
JP3078431B2 (ja) * 1993-09-27 2000-08-21 富士写真フイルム株式会社 黒白ハロゲン化銀写真感光材料の現像方法
US5399457A (en) * 1993-10-15 1995-03-21 Minnesota Mining And Manufacturing Company Process for reducing sludge in diffusion transfer printing plates
US5824458A (en) * 1994-02-28 1998-10-20 Fuji Photo Film Co., Ltd. Developer and fixing solution for silver halide photographic material and processing method using the same
US5427905A (en) 1994-07-13 1995-06-27 Polaroid Corporation Thermally processable image-recording material including reductone developing agent
US5798204A (en) * 1994-07-26 1998-08-25 Fuji Photo Film Co., Ltd. Development processing method of ultrahigh-contrast black-and-white silver halide photographic material
EP0704756B1 (fr) * 1994-09-09 2000-03-22 Konica Corporation Procédé de traitement photographique pour traitement d'un matériau photographique à l'halogénure d'argent sensible à la lumière
US5648205A (en) * 1994-10-13 1997-07-15 Fuji Photo Film Co., Ltd. Processing method for silver halide photographic material
JP3508081B2 (ja) * 1995-10-30 2004-03-22 コニカミノルタホールディングス株式会社 ハロゲン化銀写真感光材料用固体処理剤および処理方法
JP3574986B2 (ja) * 1996-01-16 2004-10-06 コニカミノルタホールディングス株式会社 ハロゲン化銀写真感光材料用固体処理剤及びハロゲン化銀写真感光材料の処理方法
FR2743905B1 (fr) 1996-01-23 1999-03-05 Kodak Pathe Composition de revelateur organique-inorganique
EP0848287A1 (fr) 1996-12-11 1998-06-17 Imation Corp. Composition de révélateur pour des matériaux photographiques à l'halogénure d'argent et procédé pour former des images photographiques d'argent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US742405A (en) * 1901-12-17 1903-10-27 Farbenfabriken Elberfeld Co Photographic plate and process of making same.
US2477462A (en) * 1946-03-26 1949-07-26 Du Pont Polymeric color formers from hydroxyl polymers containing reactive ketaldone groups with reactive methylene and amino color formers
GB679677A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to pyrazolidones
GB679678A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to the production of 3-amino pyrazolines
US2672416A (en) * 1949-11-16 1954-03-16 Austin N Stanton Reflex photography utilizing a luminescent light source

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US742405A (en) * 1901-12-17 1903-10-27 Farbenfabriken Elberfeld Co Photographic plate and process of making same.
US2477462A (en) * 1946-03-26 1949-07-26 Du Pont Polymeric color formers from hydroxyl polymers containing reactive ketaldone groups with reactive methylene and amino color formers
US2672416A (en) * 1949-11-16 1954-03-16 Austin N Stanton Reflex photography utilizing a luminescent light source
GB679677A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to pyrazolidones
GB679678A (en) * 1950-04-06 1952-09-24 Ilford Ltd Improvements in or relating to the production of 3-amino pyrazolines

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257205A (en) * 1960-10-12 1966-06-21 Gevaert Photo Prod Nv Method for heat development
US3278307A (en) * 1961-11-21 1966-10-11 Eastman Kodak Co Photographic process for producing prints stabilized against print-out
US3335007A (en) * 1962-06-15 1967-08-08 Gevaert Photo Prod Nv Silver halide diffusion transfer process
US3300307A (en) * 1963-01-18 1967-01-24 Eastman Kodak Co Photographic developer composition
US3632340A (en) * 1968-09-09 1972-01-04 Eastman Kodak Co Cored direct positive silver halide emulsion developed with polyhydroxybenzene
US4734358A (en) * 1984-10-05 1988-03-29 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
USH1119H (en) 1990-01-19 1992-12-01 Fuji Photo Film Co., Ltd. Direct positive photographic material
USH1242H (en) 1990-03-03 1993-10-05 Konica Corporation Silver halide photographic light-sensitive material
US5447826A (en) * 1991-08-16 1995-09-05 Agfa-Gevaert, N.V. Photographic silver halide material

Also Published As

Publication number Publication date
FR1106144A (fr) 1955-12-12
FR1106813A (fr) 1955-12-23
GB767704A (en) 1957-02-06
US2688548A (en) 1954-09-07
BE530883A (fr) 1957-10-25
GB767699A (en) 1957-02-06
FR1109575A (fr) 1956-01-31
US2691589A (en) 1954-10-12
BE530887A (fr) 1957-10-25

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