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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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pyrazolidone
emulsion
silver halide
emulsion layer
compounds
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US371948A
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Glay M Hood
Paul R Crookshank
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE530883D priority Critical patent/BE530883A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US372168A priority patent/US2691589A/en
Priority to US372166A priority patent/US2688548A/en
Priority to US371948A priority patent/US2751297A/en
Priority to FR1109575D priority patent/FR1109575A/en
Priority to FR1106813D priority patent/FR1106813A/en
Priority to FR1106144D priority patent/FR1106144A/en
Priority to GB22510/54A priority patent/GB767704A/en
Priority to BE530887D priority patent/BE530887A/xx
Priority to GB22505/54A priority patent/GB767699A/en
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Publication of US2751297A publication Critical patent/US2751297A/en
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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.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

June 19, 1956 HOOD EI'AL 2,751,297
PHOTOGRAPHIC EMULSION LAYER CONTAINING A 3-PYRAZOLIDONE Filed Aug. 3. 1953 S/L V E HAL/0E EMUL S/OIV CONTA/lV/IVG A 3 PYRAZOL /0 ONE l0 SUPPOR 7' 6L4 Y M. HOOD PAUL R. CROOKSHA/VK INVENTORS BY M X M ATTORNEY 8 AGENT United States Patent PHOTOGRAPHIC EMULSION LAYER CON- TAINING A 3-PYR-AZOLIDONE Glay M. Hood and Paul R. Crookshank, Rochester, N. Y
assignors to Eastman Kodak Company, N. Y., a corporation of New Jersey Application August 3, 1953, Serial No. 371,948 12 Claims. (Cl. 95-7) '9 Rochester,
it is desirable to obtain rapid and reasonably complete development of the exposed emulsion layer. Wehave discovered that if certain 3-pyrazolidone compounds are incorporated into silver halide emulsion layers, particularly those emulsion layers which-are normally slow developing or in those cases where a short complete development is desired, development proceeds much faster than when the 3-pyrazolidone compounds are not present in the emulsion layer.
The accompanying drawings show in; greatly enlarged cross-sectional view the appearance of a representative photographic element contemplated by our invention. In the element of the drawings layer represents a support such as paper, cellulose ester, etc., and 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. l-phenyl-3-pyrazolidone l-p-tolyl-3-pyrazolidone 5-phenyl-3-pyrazolidone 5-methyl-3-pyrazolidone 1-p-chlorophenyl-3-pyrazolidone 1-phenyl-S-phenyl-3pyrazolidone l-m-tolyl-3-pyrazolidone 1 phenyl-S-methyl-3-pyrazolidone 1-p-tolyl-5 phenyl-3pyrazolidone l-m-tolyl-S-pyrazolidone 2,751,297 Patented June 19, 1956 l-p-methoxyphenyl 3 pyrazolidone l-acetamidophenyl-3-pyrazolidone 1-phenyl-2-acetyl-4,4:dimethyl-3-pyrazolidone l-phenyl-4,4-dimethyl-3-pyrazolidone l-m-aminophenyl 4=methyl-4-propyl-3-pyrazolidone 'l-o-chlorophenyl-4-methyl-4-ethyl-3-pyrazolidone 'l-m-acetamidophenyl-4,4-diethyl-3-pyrazolidone l (p-fi-hydroxyethylphenyl) 4,4-dimethyl 3-pyrazolidone 1-p-hydroxyphenyl-4,4-dimethyl-3-pyrazolidone l -p-methoxyphenyl 4;4-diethyl-3pyrazolidone l-p=tolyl 4,4-dimethyl*3-pyrazolidone l (7-hydroxy-2-naphthyl) 4-methyl 4 n-p-ropyl -3- pyrazolidone l-p-diphenyl-4,4 dimethyl-3-pyrazolidone 1-(p-B-hydroxye'thylphenyl)-3-pyrazolidone l-o-tolyl3-pyrazolidone 1=o-tolyl-4,4-dimethyl-3 pyrazolidone 1-benzothiazolyl 3 pyrazolidone Compounds l to '12 can be prepared by the methods described in British Patents 679,677 and 679,678. Compounds 13 to 23 and26above are representative of 4,4- dialkyl-3-pyrazolidone compounds useful in the'invention and these compounds are described and claimed in the Allen et al. U. 'S.,patent application Serial No. 372,148, filed August 3,1953.
The w-hydroxyalkylphenyl-3-pyrazo1idones in which the "alkylgroup preferably contains from 1 to 4 carbon atoms, for example, compoundslS and 24 above, are described in the Allen et al. invention and in the Reynolds and "Tin'ker U; su patenttapplication Serial No. 372,167, filed concurrently.
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. However,'both smaller and largeriquantities of'the'compounds than indicated can be. used with good results. The particular silver halide infthe emulsioniis not especially critical nor is the particular'method used for preparing the emulsion. Thus 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. However; 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. According to our invention, such color films carry at-least .one emulsion layer containing one or more of the-pyrazoemulsion or to stabilize it can be incorporated in :a hydrophilic colloid layer such asgelatin adjacent -to.=the
emulsion layer with the result. that materialdevelopment acceleration and improvement in emulsion :stabilityere obtained thereby.
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. In considering the data of the table, 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.
What we claim is:
1. 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. R
Use of pyrazolidones in a washed bromoiodide emulsion Bar Gamma D-rnax.
tar I B on, Chemical mglmole 20 Sec. Dev. Bee. Dev. 20 Sec. Dev. 45 See. Dev.
Silver Halide Fresh 3Day Fresh 3108. Fresh 3Day Fresh 3Day Inc. Inc. 1110. Inc.
Check None 1.00 s1 1. 7a 1. 1. 01 s9 1. 2a 1. 25 it? is: 1a 1a 112 5 .28 0 437 1. 41 95 1. ss 1. 70 1. 1s 1. 12 1. 27 1. as 219 1. 21 .93 1. s9 1. as 1.15 1. 04 1. 27 1. 2e at 1a 1a 1a 4'"dimeihYLl'phenyl'ii'pyrawndune 431 1: 25 I as 1185 11 e5 11 1g 11 11 2; i1 2% 219 1. 20 .93 1. s3 1. 65 1. 15 1.00 1. 27 1. 2s tit l-tt tit it; 1a 12 1e htdimethym@myn'a'pymtlmm wis? 11 29 I as 1161 1'. s2 1: 15 1102 11 is iI 219 76 9s 1. 71 1. 64 9s 1. 02 1. 25 1. 24 1, 75% 1.32 1.22 39 13 1 2 21 1.27 1'(Mflydmyeihybphwyl)'a'pmmndme--'- 237 1: 21; I91 11 11 1: 62 110 110 1122 i1 3% 219 1. 59 .so 1. e9 1. 1. 04 1.10 1. 25 1. 24
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. The data obtained showed that the gamma for samples of the emulsion containing no pyrazolidone compound which were developed 15, 30 and 45 seconds respectively, were 0.75, 0.98 and 1.05, whereas the samples containing the pyrazolidone compound developed under the same conditions had gammas of 1.08, 1.27 and 1.35. This example illustrates the effect which may be expected in reversal processes where it is desired to obtain a rapid complete development of the negative image where the first or negative development is usually short.
The other 3-pyrazolidone compounds such as those specifically mentioned above are useful in our invention as accelerators and stabitizers for emulsions. As men- 55 wherein R represents a mononuclear aryl group of the benzene series and R1 and R2 each represent an alkyl group of 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.
3. 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.
4. 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.
5. 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
emulsion.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
References Cited in the file of this patent UNITED STATES PATENTS 742,405 Eichengrun et al. Oct. 27, 1903 2,477,462 McQueen July 26, 1949 2,672,416 Stanton Mar. 16, 1954 FOREIGN PATENTS 679,677 Great Britain Sept. 24, 1952 679,678 Great Britain Sept. 24, 1952

Claims (1)

1. A LIGHT-SENSITIVE PHOTOGRAPHIC EMULSION COMPRISING A MIXTURE OF UNEXPOSED SILVER HALIDE AND A 3-PYRAZOLIDONE HAVING THE FOLLOWING GENERAL STRUCTURE
US371948A 1953-08-03 1953-08-03 Photographic emulsion layer containing a 3-pyrazolidone Expired - Lifetime US2751297A (en)

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

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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
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US3278307A (en) * 1961-11-21 1966-10-11 Eastman Kodak Co Photographic process for producing prints stabilized against print-out
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US3300307A (en) * 1963-01-18 1967-01-24 Eastman Kodak Co Photographic developer composition
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BE530883A (en) 1957-10-25
GB767699A (en) 1957-02-06
BE530887A (en) 1957-10-25
FR1109575A (en) 1956-01-31
GB767704A (en) 1957-02-06
FR1106144A (en) 1955-12-12
US2688548A (en) 1954-09-07
FR1106813A (en) 1955-12-23
US2691589A (en) 1954-10-12

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