US2680686A - Sensitized and supersensitized photographic emulsions - Google Patents

Sensitized and supersensitized photographic emulsions Download PDF

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Publication number
US2680686A
US2680686A US141601A US14160150A US2680686A US 2680686 A US2680686 A US 2680686A US 141601 A US141601 A US 141601A US 14160150 A US14160150 A US 14160150A US 2680686 A US2680686 A US 2680686A
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United States
Prior art keywords
formula
emulsion
supersensitized
compound
silver
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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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US141601A
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English (en)
Inventor
Andre Emile Van Dormael
Nys Jean Marie
Cat Arthur Henri De
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms
    • 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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/28—Sensitivity-increasing substances together with supersensitising 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
    • G03C1/08—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

  • G A COMPOUND OF FORMULA Y. F 5 HaA DYE OF FORMULA XIII.
  • M A COMPOUND OF FORMULA 1:.
  • N A DYE or: FORMULA 12m.
  • the present invention relates to a process for the production of photographic silver halide emulsions.
  • This invention more particularly relates to the sensitization and supersensitization of photographic silver halide emulsions.
  • An object of the present invention is to provide a new process for sensitizing and supersonsitizing photographic emulsions.
  • a further object is to provide a photographic element comprising an emulsion sensitized or supersensitized according to our new process.
  • R' a member selected from the group consisting of a substituted acyl group, a not substituted acyl-group, a substituted amido group and a not-substituted amido group.
  • the compound of the formula ner A mixture of 2 g. N-methyl-2-imino-dihydrobenzthiazole and 0.8.. g.: ethyl-malonate is heated at 170 C. for 1.hour. .After cooling, the
  • Example 2 55 i' 'lhe spectral sensitivity of-lasilver chloride emulsion is increased by using 50 mg./kg. of the compound of the formula prepared as follows: g. N-phenyl-2-imino-dihydrobenzthiazole in 50 cm. acetic anhydride are heated at boiling temperature. After cooling,
  • Example 4 A silver bromide emulsion, containing per kg. of emulsion 20 mg. cyanine of the formula rig N is supersensitized by simultaneously using 30 mg./kg. of the derivative of the formula S CH:
  • Example 7 A silver chloride emulsion, containing per kg. of emulsion 20 mg. trimethincyanine of the formula which may be prepared as follows: A suspension of 5 g. N-methyl-2-imino-dihydrobenzthiazole in cm. acetic anhydride is refluxed for 15 minutes. After adding 100 cm. diluted alcohol (70%) the mixture is heated once more at boiling temperature for 5 minutes whereafter the product is precipitated by ice-water. Melting point (after recrystallisation from alcohol) Bil-142 C.
  • Emample 5 A silver chloride emulsion, containing per kg. of emulsion 6 mg. trimethincyanine of the formula CHa-CHn-CH:
  • T 02115 prepared as follows: A mixture of 3.3 g. N- 01 01 Brmethyl-2-imino-dihydrobenzthiazole and 0.6 g. 'urea is melted at about 180 C. for 1 hour. After Ha CH3 cooling, the product is extracted by boiling water. Aft cooling, the product obtained is Sucked off is strongly supersensitized by simultaneously and recrystallised from alcohol. Melting point: using mgJkgof the compound of the formula 224-226 C.
  • Example 9 30 A silver chloro-bromide emulsion, containing per kg. of emulsion 10 mg. pentamethincyanine of NH the formula (I:
  • Example13 prepared as follows: A mixture of 4 g.
  • Example 14 2 carhethoxymethyl benzthiazole in l cm.
  • a silver chloro-bromide emulsion, containing Xylene, is heated for 4 h s a boiling e p aper kg. of emulsion 10 mg. trimethincyanine of ture in the presence of 5 drops pyridine.
  • a prodr EHPCHZCHE i 1 I c-on is obtained from a silver chloro-bromide emulsion, containing Xylene, is heated for 4 h s a boiling e p aper kg. of emulsion 10 mg. trimethincyanine of ture in the presence of 5 drops pyridine.
  • a prodr EHPCHZCHE i 1 I c-on on
  • FIG. 1 The specification is accompanied by drawings to illustrate the supersensitizing efiect obtained with five of our new dyestuff combinations used in silver halide emulsions.
  • FIG. 1 to 5 is a diagrammatic reproduction of three spectrograms. In each figure, the sensitivity is represented by a dotted line; the sensitivity of the emulsion containing only the cyanine dye is represented by a dash-dotted line; and the sensitivity of the emulsion containing the compound according to the invention in combination with the cyanine dye is represented by the solid line.
  • a photographic silver halide emulsion containing the compound of the formula 2.
  • a photographic silver halide emulsion containing the combination of the dyestufi of the formula l0 and the dyestuff of the formula than N References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,080,049 Kendall May 11, 1937 2,153,930 Kendall Apr. 11, 1939 2,177,635 Carroll et a1 Oct. 31, 1939 2,298,732 Brooker et a1. Oct. 13, 1942 2,312,040 Kendall et a1. Feb. 23, 1943 2,340,882 Kendall Feb. 8, 1944 2,490,745 Carroll et a1 Dec. 6, 1949 2,503,861 Weissberger Apr. 11, 1950 FOREIGN PATENTS Number Country Date I 617,720 Great Britain Feb. 10, 1949

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US141601A 1949-02-01 1950-01-31 Sensitized and supersensitized photographic emulsions Expired - Lifetime US2680686A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR812872X 1949-02-01

Publications (1)

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US2680686A true US2680686A (en) 1954-06-08

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US (1) US2680686A (fr)
DE (1) DE812872C (fr)
FR (1) FR979853A (fr)
GB (1) GB684166A (fr)
NL (1) NL72814C (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2848329A (en) * 1956-05-14 1958-08-19 Eastman Kodak Co Supersensitization with bis-heterocyclic bases
US2852385A (en) * 1956-05-14 1958-09-16 Eastman Kodak Co Supersensitization of photographic emulsions

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2080049A (en) * 1934-08-03 1937-05-11 Ilford Ltd Production of dyes of the cyanine type
US2153930A (en) * 1935-05-08 1939-04-11 Ilford Ltd Sensitized photographic emulsion
US2177635A (en) * 1937-05-29 1939-10-31 Eastman Kodak Co Photographic emulsion
US2298732A (en) * 1940-12-16 1942-10-13 Eastman Kodak Co Polymethine base
US2312040A (en) * 1938-07-22 1943-02-23 Ilford Ltd Production of colored photographic images by color development and composition therefor
US2340882A (en) * 1935-08-16 1944-02-08 Ilford Ltd Sensitized photographic material
GB617720A (en) * 1944-03-21 1949-02-10 Dastman Kodak Company Improvements in or relating to photography
US2490745A (en) * 1948-01-13 1949-12-06 Eastman Kodak Co Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts
US2503861A (en) * 1949-03-02 1950-04-11 Eastman Kodak Co 2-(mercaptoacetamido)-benzothiazole and its s-acetyl derivative

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2080049A (en) * 1934-08-03 1937-05-11 Ilford Ltd Production of dyes of the cyanine type
US2153930A (en) * 1935-05-08 1939-04-11 Ilford Ltd Sensitized photographic emulsion
US2340882A (en) * 1935-08-16 1944-02-08 Ilford Ltd Sensitized photographic material
US2177635A (en) * 1937-05-29 1939-10-31 Eastman Kodak Co Photographic emulsion
US2312040A (en) * 1938-07-22 1943-02-23 Ilford Ltd Production of colored photographic images by color development and composition therefor
US2298732A (en) * 1940-12-16 1942-10-13 Eastman Kodak Co Polymethine base
GB617720A (en) * 1944-03-21 1949-02-10 Dastman Kodak Company Improvements in or relating to photography
US2490745A (en) * 1948-01-13 1949-12-06 Eastman Kodak Co Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts
US2503861A (en) * 1949-03-02 1950-04-11 Eastman Kodak Co 2-(mercaptoacetamido)-benzothiazole and its s-acetyl derivative

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2848329A (en) * 1956-05-14 1958-08-19 Eastman Kodak Co Supersensitization with bis-heterocyclic bases
US2852385A (en) * 1956-05-14 1958-09-16 Eastman Kodak Co Supersensitization of photographic emulsions

Also Published As

Publication number Publication date
NL72814C (fr)
FR979853A (fr) 1951-05-04
DE812872C (de) 1951-09-06
GB684166A (en) 1952-12-10

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