US2680686A - Sensitized and supersensitized photographic emulsions - Google Patents
Sensitized and supersensitized photographic emulsions Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- formula
- emulsion
- supersensitized
- compound
- silver
- 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 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 SILVER HALIDE Chemical class 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 5
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 5
- UBKQDYMDQHJMCL-UHFFFAOYSA-N 3-methyl-3a,4-dihydro-1,3-benzothiazol-2-imine Chemical compound CN1C(SC=2C1CC=CC2)=N UBKQDYMDQHJMCL-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910021607 Silver chloride Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- BDDPKGFJGYIFHV-UHFFFAOYSA-N 3-phenyl-3a,4-dihydro-1,3-benzothiazol-2-imine Chemical compound C1(=CC=CC=C1)N1C(SC=2C1CC=CC2)=N BDDPKGFJGYIFHV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Images
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR812872X | 1949-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2680686A true US2680686A (en) | 1954-06-08 |
Family
ID=9265867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US141601A Expired - Lifetime US2680686A (en) | 1949-02-01 | 1950-01-31 | Sensitized and supersensitized photographic emulsions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2680686A (enMihai) |
| DE (1) | DE812872C (enMihai) |
| FR (1) | FR979853A (enMihai) |
| GB (1) | GB684166A (enMihai) |
| NL (1) | NL72814C (enMihai) |
Cited By (2)
| 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)
| 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 |
-
0
- NL NL72814D patent/NL72814C/xx active
-
1949
- 1949-02-01 FR FR979853D patent/FR979853A/fr not_active Expired
-
1950
- 1950-01-28 DE DEG922A patent/DE812872C/de not_active Expired
- 1950-01-31 US US141601A patent/US2680686A/en not_active Expired - Lifetime
- 1950-01-31 GB GB2501/50A patent/GB684166A/en not_active Expired
Patent Citations (9)
| 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)
| 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 |
|---|---|
| DE812872C (de) | 1951-09-06 |
| GB684166A (en) | 1952-12-10 |
| NL72814C (enMihai) | |
| FR979853A (fr) | 1951-05-04 |
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