US2644754A - Supersensitized photographic silver halide emulsions - Google Patents

Supersensitized photographic silver halide emulsions Download PDF

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Publication number
US2644754A
US2644754A US766098A US76609847A US2644754A US 2644754 A US2644754 A US 2644754A US 766098 A US766098 A US 766098A US 76609847 A US76609847 A US 76609847A US 2644754 A US2644754 A US 2644754A
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United States
Prior art keywords
methyl
phenyl
iodide
silver halide
photographic silver
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Expired - Lifetime
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US766098A
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English (en)
Inventor
Jennen Jacob Joseph
Vandenbroele Oscar Hendrik
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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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
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed

Definitions

  • the effect of a sensitizer is not in proportion to the quantity added to the emulsion; it passes through a certain maximum by raised concentration.
  • a combination of sensitizers usually does not produce a larger effect; it often causes but a smaller effect than a single sensitizer when the latter is used in a concentration equal to the sum of the concentrations of the mixed dyestuffs.
  • Known added dyestuffs are mesosubstituted carbocyanines of the following-general formula:
  • Z is non-metallic atoms required to complete a heterocyclic ring, or thio and seleno-4'- carbocyanines:
  • Another object of the present invention isv to provide new photographic silver halide emul- 810115.
  • the hydrogen 'of the open chain may berepla'ced. by hydrocarbon groups, halogen or carboncontaining bridges.
  • the compounds totbe usedin accordance with our invention since being easily soluble, mostly even water-soluble can, fromatechnical point of view, easily b'ehandled, i. "e., withoutthe use of any organic solvents. For this very reason, they are also unstable in photographic baths so that after bathing colorless photographic layers are obtained.
  • the curve A represents the sensitivity o of an emulsion containing 3,3'diethy1-2,2'- -cya.-
  • the curve B represents the sensi? tivity of the same emulsion containing l-phenyl- 3 methyl 5 hydroxypyrazolyl alphamethyl 7 trimethine 1 phenyl 3 methyl 5- pyrazolone p p di-ammonium sulphonate.
  • the curve C represents the sensitivity 'of the same emulsion containing 3,3 -'diethy1- 2,2 -cyanine 4 phenyl thiazo lo 2 iodide, and. l .p henyl 3 methyl 5 -hydroxypyraz'olyl ⁇ alpha' methyl trimethine' 1- phenyl 3"'-' methyl 5 pyrazolonep p diammonium sulphonate.
  • the curve D represents the sensitivity of an emulsion containing 3 ,3-diethy1-2, 2 -cyanine iodide.
  • the curve E re resents the sensitivity of the same emulsion containing l-phenyl- 3 methyl 5 hydroxypyrazolyl alpha betabutylenetrimethine 1 phenyl 3 methyl 5- pyrazolone p p di ammonium sulphonate.
  • the curve F represents the sensitivity of an emulsion containing 3,3-diethyl-2,2-cyanine iodide and 1 phenyl 3 methyl 5 hydroxypyrazolyl alpha beta butylenetrimethine 1- phenyl 3 methyl 5 pyrazolone pp diammonium sulphonate.
  • the curve G represents the sensitivity of an emulsion containing 3,3-9-triethyl-6,7,- 6,7'-dibenzoxocarbocyanine iodide.
  • the curve H represents the sensitivity of the same emulsion containing 1 phenyl 3 methyl 5 hydroxypyrazolyl alpha methyl trimethine 1- phenyl 3 methyl 5 pyrazolone pp diammonium sulphonate.
  • the curve I represents the sensitivity of the same emulsion containing 3,3 9 triethyl 6,7,6)?
  • the curve J represents the sensitivity of an emulsion containing 3,3 9 triethyl 6,7,- 6',7'-dibenzoxocarbocyanine iodide.
  • the curve K represents the sensitivity of the same emulsion containing 1 phenyl 3 methyl 5 hydroxypyrazolyl alpha beta butylenetrimethine- 1 phenyl 3 methyl 5 pyraz'olone p pdi-ammonium sulphonate.
  • the curve L represents the sensitivity of the same emulsion containing 3,3 9 triethyl 6,7,6',7 dibenzoxocarbocyanine iodide and l-phenyl-3-methyl-5- hydroxypyrazolyl alpha beta butylenetrimethine 1 phenyl 3 methyl 5 pyrazolonep-p-di-ammonium sulphonate.
  • This invention may be applied to ordinary silver halide gelatine emulsions.
  • the dyestuiT combinations of our invention- may also be used in emulsions wherein instead of gelatine another binder is employed, as, e. g., resinous substances or cellulose derivatives, this without a noxious influence upon the light-sensitive substance.
  • the dyestufi" of Example 2 the preparation of which has not been described yet may be obtained by condensation of phenylmethylpyrazolone-pammonium sulphonate with sodium-oxymethylene-cyclohexanone in methyl alcohol as disclosed in the co-pending application Serial No. 766,097, filed August 4, 1947.
  • the dyestuif 5-hydroxy-3- phenylisoxazolyl alpha carbethoxy alphamethyltrimethine-3-phenylisoxazolone-5 may be prepared as follows: 0.02 mol phenylisoxazolone, 0.01 mol sodium acetyl pyruvic acid ethyl ester and 60 cm. methyl alcohol are heated on the water bath for two hours whereafter the intensive-violet colored mixture is poured into 400 cm.
  • the absorption maximum of this violet dyestuff which is probably the dyestuif of Example 4, lies at about 592 my"
  • the dyestufi (l-oxo-B-oxyhydrindyl- -Z)-betachlorotrimethine-indandione is prepared as follows: 0.02 mol indandione, 0.04 mol chloromalondialdehyde dianilhydrochloride and 0.02 mol sodium hydroxide are mixed in 250 cm. methylalcohol and allowed to remain for two days. the formed crystals are drained and washed with ether. The dyestuif obtained is probably that of- Example 5.
  • the dyestufis may be mixed with the emulsion either ins dividually or in combinations.
  • Photographic silver halide emulsion having incorporated therein a supersensitizing dyestuff composition
  • a supersensitizing dyestuff composition comprising at least one sensitizing dyestufi and at least one polymethine dyestufi, said sensitizing dyestufi being selected from the group consisting of 3,3 diethyl 2,2 cyanine iodide and 3,3,9-triethyl-6,7,6',7-dibenzoxocarbocyanine iodide, said polymethine dyestufi having the following general formula:
  • a photographic silver halide emulsion having incorporated therein a supersensiti zing dye stuff composition comprising 3,3 diethyl 2,2-

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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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Indole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US766098A 1941-05-22 1947-08-04 Supersensitized photographic silver halide emulsions Expired - Lifetime US2644754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE626467X 1941-05-22

Publications (1)

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US2644754A true US2644754A (en) 1953-07-07

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US (1) US2644754A (en(2012))
BE (1) BE445646A (en(2012))
ES (1) ES157458A1 (en(2012))
FR (1) FR882245A (en(2012))
GB (1) GB626467A (en(2012))
NL (1) NL61612C (en(2012))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830883A (en) * 1954-04-29 1958-04-15 Texas Co Gasification of sulfur-bearing carbonaceous fuels
EP0866364A1 (de) * 1997-03-18 1998-09-23 Agfa-Gevaert AG Hochempfindliches farbfotografisches Aufzeichnungsmaterial mit erhöhter Empfindlichkeit im blauen Spektralbereich

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE560805A (en(2012)) * 1956-09-13

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2127340A (en) * 1937-03-29 1938-08-16 Eastman Kodak Co Photographic emulsion containing supersensitized thiazolocarbocyanines
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process
US2274782A (en) * 1937-11-24 1942-03-03 Chromogen Inc Light-sensitive photographic material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2127340A (en) * 1937-03-29 1938-08-16 Eastman Kodak Co Photographic emulsion containing supersensitized thiazolocarbocyanines
US2274782A (en) * 1937-11-24 1942-03-03 Chromogen Inc Light-sensitive photographic material
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830883A (en) * 1954-04-29 1958-04-15 Texas Co Gasification of sulfur-bearing carbonaceous fuels
EP0866364A1 (de) * 1997-03-18 1998-09-23 Agfa-Gevaert AG Hochempfindliches farbfotografisches Aufzeichnungsmaterial mit erhöhter Empfindlichkeit im blauen Spektralbereich
US6040125A (en) * 1997-03-18 2000-03-21 Agfa-Gevaert Nv High-speed color photographic recording material having increased sensitivity in the blue spectral region

Also Published As

Publication number Publication date
NL61612C (en(2012))
BE445646A (en(2012))
ES157458A1 (es) 1943-03-01
GB626467A (en) 1949-07-15
FR882245A (fr) 1943-05-21

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