US2450748A - Photographic silver halide emulsion supersensitized with a c-acyloxy quinoline base - Google Patents
Photographic silver halide emulsion supersensitized with a c-acyloxy quinoline base Download PDFInfo
- Publication number
- US2450748A US2450748A US663762A US66376246A US2450748A US 2450748 A US2450748 A US 2450748A US 663762 A US663762 A US 663762A US 66376246 A US66376246 A US 66376246A US 2450748 A US2450748 A US 2450748A
- Authority
- US
- United States
- Prior art keywords
- emulsion
- silver
- quinoline base
- emulsions
- acyloxy
- 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
Links
- 239000000839 emulsion Substances 0.000 title description 67
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 47
- 229910052709 silver Inorganic materials 0.000 title description 7
- 239000004332 silver Substances 0.000 title description 7
- -1 silver halide Chemical class 0.000 title description 4
- 239000000975 dye Substances 0.000 description 21
- 230000035945 sensitivity Effects 0.000 description 18
- 230000003595 spectral effect Effects 0.000 description 14
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 13
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 230000029087 digestion Effects 0.000 description 5
- 230000001235 sensitizing effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- NJXWZWXCHBNOOG-UHFFFAOYSA-N 3,3-diphenylpropyl(1-phenylethyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C)[NH2+]CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NJXWZWXCHBNOOG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BHXCPQHXDLLGAV-UHFFFAOYSA-N quinolin-6-yl acetate Chemical compound N1=CC=CC2=CC(OC(=O)C)=CC=C21 BHXCPQHXDLLGAV-UHFFFAOYSA-N 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- LQNGSCMDXDEBEI-UHFFFAOYSA-N 6-phenylmethoxyquinoline Chemical compound C=1C=C2N=CC=CC2=CC=1OCC1=CC=CC=C1 LQNGSCMDXDEBEI-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102100022430 Melanocyte protein PMEL Human genes 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 108091058557 SILV Proteins 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- LAABTJXWUKMZIV-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 LAABTJXWUKMZIV-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- CNNBEXYIRHCJBH-UHFFFAOYSA-N quinolin-2-yl acetate Chemical compound C1=CC=CC2=NC(OC(=O)C)=CC=C21 CNNBEXYIRHCJBH-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- 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
- G03C1/12—Methine and polymethine dyes
-
- 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
Definitions
- This invention relates to sensitized photographic emulsions and to a process for preparing the same.
- This application is a continuation-inpart of our copendi ng application Serial No. 466,796, filed November 24, 1942 (now United States Patent 2,398,778, dated April 23, 1946).
- a photographic silver halide emulsion other than a chloride emulsion e. g. silver chlorobromide (which may contain small amounts of silver iodide), silver bromide or silver trally sensitized with a (at least one) cyanine dye is supersensitized by incorporating in the emulsion a (at least one) quinoline base containing an (at least one) acyloxy (acyloxyl) group attached to a (at least one) carbon atom of the quinoline base.
- a photographic silver halide emulsion other than a chloride emulsion e. g. silver chlorobromide (which may contain small amounts of silver iodide), silver bromide or silver trally sensitized with a (at least one) cyanine dye is supersensitized by incorporating in the emulsion a (at least one) quinoline base containing an (at least one) acyloxy (acyloxyl)
- Our invention is directed principally to emulsions of such grain size that the bromiodide emulsions, spec- I 2 emulsions give a substantially neutral-toned image in Eastman Kodak Company's D76 developer, and should not be confused with prior proposals to obtain blue-black tones in fine-grain emulsions by means of heterocyclic nitrogen bases.
- our invention involves incorporation of the quinoline bases in the emulsion before exposure of the emulsion and should not be confused with proposals to develop with colorforming developers silver salt images, in the presence of certain heterocyclic nitrogen bases which contain a reactive methyl group.
- the quinoline bases employed in practicing our invention are quinoline bases containing an acyloxyl group attached to a carbon atom of the quinoline base.
- the acyloxy group is an acetoxy group or a benzoxy group.
- the acyloxyquinolines include 6- acetoxyquinoline, 2-acetoxyquinoline, fi-benzoxyquinoline, etc. v
- cyanine dyes which are super.- sensitized by the quinoline bases are characterized by the fact that the dyes produce two types of sensitization depending upon conditions. Such different types of sensitization are described by Leermakers, Carroll and Stand, J. Chem. Physics 5, 878 (1937) and by Schwarz, Sci. et Ind. Phot. 10, 233 (1939).
- a cyanine dye of this type is used as a sensitizer in low concentration, it e nowadays- hibits a sensitizing maximum displaced about20 to m toward the red from the absorption maximum in ethyl alcohol solution.
- siuin line bases can be added to he emulsions w th. b for or after thesens tiz n dy or dyes.
- Th euinoliu bases are nreterably. but ot nec ssan y. dilu ed with a water-miscibl s lvent. su h as m than l, before inaorn ration in t e mulsi nshe sensit insdye. or dy sanrd the u ncl ne as or ba es ca be add d o th em lu ns at an n i t st e f their pr parat n but p efer bly t -the washed, fore coating.
- the accompanying drawing illustrates graphically the supersensitizing effect obtained with one of our new combinations in a gelatino-silverbromoiodide emulsion,
- the figure is a diagrammatic reproduction of two spectrograms.
- Curve A represents the sensitivity of the emulsion sensit i z e d with 3,3-diethy1 9 methylselenacarbocyin a concentration of 20 mg. per liter of emulsion.
- Curve 3 represents the sensitivity of the same emulsion sensitized'with 3,3- diethyl-9-methylselenacarbocyanine bromide in a concentration of 20 mg.
- G-acetoxyquinoline having also been added to the emulsion in a concentration of 0.25 cc. per liter of emulsion.
- the supersensitizing or synergistic eiTect of the combination is apparent.
- G-Acetoxyquinoline, alone, imparts no additional spectral sensitivity to the emulsion.
- Our invention is primarily directed to the customarily employed gelatino-silver-halide developing-out emulsions, such as gelatino-silver-chlorobromide, gelatino-silver-bromide and gelatino silver-bromiodide developing-out emulsions, esfor development to black-andwhite images by means of non-color-formin developers, e, g. hydroquinone-N-methyl-p-aminophenol developers.
- non-color-formin developers e, g. hydroquinone-N-methyl-p-aminophenol developers.
- Emulsions prepared in accordance with our invention can be coated in th usual manner upon any desired support, such as cellulose nitrate support, cellulose acetate support, polyvinyl aoetal resin support, metal support, glass support or paper support.
- a photographic silver halide emulsion selectedfrom the group consisting of silver chlorobromide, silver bromide and silver bromiodide emulsions spectrally sensitized with a sensitizing cyanine dye containing, as a supersensitizer, a u n i e ba QI BI an acyloxy o p r tached to a carbon atom of the quinoline base.
- a photographic gelatino-silver-halide developing-out emulsion selected from the group consisting of gelatino-silver-chlorobromide, gelatino-silver-bromide and gelatino-silver-bromiodide developing-out emulsions spectrally sensitized with a cyanine dye which produces a maximum of spectral sensitivity in the emulsion at one concentration and at a higher concentration, or upon digestion of the emulsion at the lower concentration, produces a second maximum of spectral sensitivity at a wavelength longer than that of the first maximum, said emulsion containing as a supersensitizer, a quinoline base containing an acyloxy group attached to a carbon atom of the quinoline base.
- a photographic gelatino-silver-bromiodide developing-out emulsion spectrally sensitized with a cyanine dye which produces a maximum of spectral sensitivity in the emulsion at one con centration and at a higher concentration, or upon digestion of the emulsion at the lower concentration, produces a second maximum of spectral sensitivity at. a wavelength longer than that of the first maximum, said emulsion containing, as a supersensitizer, a quinoline base containing a benzoxy group attached to a carbon atom of the quinoline base.
Landscapes
- 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)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE472645D BE472645A (is") | 1946-04-20 | ||
| US663762A US2450748A (en) | 1946-04-20 | 1946-04-20 | Photographic silver halide emulsion supersensitized with a c-acyloxy quinoline base |
| GB10452/47A GB635623A (en) | 1946-04-20 | 1947-04-18 | Sensitive photographic emulsions |
| FR55346D FR55346E (fr) | 1946-04-20 | 1947-04-19 | Perfectionnements relatifs aux émulsions photographiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US663762A US2450748A (en) | 1946-04-20 | 1946-04-20 | Photographic silver halide emulsion supersensitized with a c-acyloxy quinoline base |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2450748A true US2450748A (en) | 1948-10-05 |
Family
ID=24663171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US663762A Expired - Lifetime US2450748A (en) | 1946-04-20 | 1946-04-20 | Photographic silver halide emulsion supersensitized with a c-acyloxy quinoline base |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2450748A (is") |
| BE (1) | BE472645A (is") |
| FR (1) | FR55346E (is") |
| GB (1) | GB635623A (is") |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049456A (en) * | 1975-04-14 | 1977-09-20 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2158882A (en) * | 1937-01-16 | 1939-05-16 | Eastman Kodak Co | Photographic emulsion |
-
0
- BE BE472645D patent/BE472645A/xx unknown
-
1946
- 1946-04-20 US US663762A patent/US2450748A/en not_active Expired - Lifetime
-
1947
- 1947-04-18 GB GB10452/47A patent/GB635623A/en not_active Expired
- 1947-04-19 FR FR55346D patent/FR55346E/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2158882A (en) * | 1937-01-16 | 1939-05-16 | Eastman Kodak Co | Photographic emulsion |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049456A (en) * | 1975-04-14 | 1977-09-20 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| BE472645A (is") | |
| FR55346E (fr) | 1952-01-02 |
| GB635623A (en) | 1950-04-12 |
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