US3770449A - Spectrally sensitized silver halide photographic emulsion - Google Patents
Spectrally sensitized silver halide photographic emulsion Download PDFInfo
- Publication number
- US3770449A US3770449A US00183492A US3770449DA US3770449A US 3770449 A US3770449 A US 3770449A US 00183492 A US00183492 A US 00183492A US 3770449D A US3770449D A US 3770449DA US 3770449 A US3770449 A US 3770449A
- Authority
- US
- United States
- Prior art keywords
- agbr
- dye
- silver halide
- halide photographic
- photographic emulsion
- 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
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- 239000000839 emulsion Substances 0.000 title claims abstract description 39
- -1 silver halide Chemical class 0.000 title claims abstract description 32
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 22
- 239000004332 silver Substances 0.000 title claims abstract description 22
- 230000001235 sensitizing effect Effects 0.000 claims abstract description 38
- 239000000298 carbocyanine Substances 0.000 claims abstract description 9
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 18
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001450 anions Chemical class 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 47
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 36
- 230000035945 sensitivity Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000586 desensitisation Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- NIPMJVLJVGQZRB-UHFFFAOYSA-N Cl[IH]Br Chemical compound Cl[IH]Br NIPMJVLJVGQZRB-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000126 substance Substances 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
- G03C1/28—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Definitions
- ABSTRACT A silver halide photographic emulsion containing a supersensitizing combination of at least one carbocyanine dye having a heterocyclic necleus comprising a benzothiazole or benzoselenazole nucleus, at least one of the heterocyclic nuclei having an acetylamino group at the 5-position thereof, and having a sensitized maximum portion within the range of from 600 to 660 nm, and at least one sensitizing dye of the following general formula (ll)' wherein R and R each represents a lower alkyl group; A represents a lower alkyl group or an aryl group; Z and Z each represents an atomic group necessary to complete a benzothiazole, benzoselenazole or B-naphthothiazole nucleus; X represents an anion; and m is 0 or 1, m being 0 when an intermolecular salt is formed.
- This invention relates to a spectrally sensitized silver halide photographic emulsion and more especially to a silver halide photographic emulsion which is supersensitized by the combined use of at least two sensitizing dyes resulting in a high red sensitivity.
- sensitizing dyes which are in supersensitization relation to each other and have a small inherent desensitization, Le, a less desensitization, in the wavelength region inherent to silver halide grains.
- the object of this invention is to provide a silver halide photographic emulsion having a panchromatically sensitized region, particularly a high red sensitivity within the spectrosensitized wavelength region of 640-685 nm and a small inherent desensitization by the combined use of two different types of sensitizing dyes.
- a panchromatically sensitized region is used generally for black and white photographic sensitive materials.
- the object of this invention has been accomplished by the combined use of a carbocyanine dye comprising heretocyclic nuclei selected from benzothiazole and benzoselenazole nuclei, at least one of the heterocyclic nuclei having an acetylamino group at the 5-position thereof, and having a sensitized maximum portion within the range of from 600 to 660 nm., preferably of the following general formula (I), and a sensitizing dye of the general formula (II) in a silver halide photographic emulsion:
- R l and R each represents a lower alkyl group, e.g., methyl, ethyl, 'y-sulfopropyl, 'y-sulfobutyl, 6-sulfobutyl, allyl etc.;
- A represents a lower alkyl group, e.g., methyl, ethyl etc.;
- 2 represents an atomic group necessary to complete a benzothiazole or benzoselenazole nucleus, which may be substituted by a halogen atom, e.g., chlorine, etc., a lower alkyl group, e.g., methyl, ethyl, etc.; an alkoxyl group, e.g., methoxy, ethoxy, etc.; or a phenyl group;
- Z represents a sulfur or selenium atom;
- X represents an anion, e.g., a chloride, bromide, io
- R and R each represents lower alkyl, e.g. methyl, ethyl, 'y-sulfopropyl, 'y-sulfobutyl, 8-sulfobutyl, B-hydroxyalkyl, B-carboxyalkyl, etc.;
- A represents lower alkyl, e.g. methyl, ethyl, etc., or an aryl group, e.g. phenyl;
- Z and Z each represents an atomic group necessary to complete a benzothiazole, benzoselenazole or B-naphthothiazole nucleus, which maybe sub-- stituted by a halogen, e.g.
- a lower alkyl group e.g. methyl, ethyl, etc.; alkoxy, e.g. m'ethoxy, ethoxy etc.; a hydroxyl group or a phenyl group;
- X represents an anion, e.g., a chloride, bromide. iodide, p-toluene sulfonate or benzenesulfonate ion, etc. and those used generally in the art;
- FIGS. 1-4 are spectograms illustrating the supersensitization effects of the combination of dyes according to the present invention.
- the combined use of the sensitizing dyes according to this invention provides a silver halide emulsion having a higher red sensitivity compared to the use of each sensitizing dye alone and, at the same time, a very small inherent desensitization.
- Another sensitizing dye for improving the .green sensitivity e.g., 2,2-cyanine, thia* 2 -cyani ne etc.
- another sensitizing dye for improving the .green sensitivity e.g., 2,2-cyanine, thia* 2 -cyani ne etc.
- those having other s jE ctral sensitizing wavelength regions e.g., 2,2-cyanine, thia* 2 -cyani ne etc.
- sensitizing dyes used in this invention are mentioned as follows, but the sensitizing dyes used in this invention are not to be restricted only to those examples.
- the carbocyanine dyes and sensitizing dyes of the general formula (II) which are used in this invention can be synthesized by a known method.
- a known method for example, with reference to US. Pat. No. 2,503,776 and German Pat. Nos. 929,080 and 1,072,765, those skilled in the art can readily synthesize them.
- the solvent is distilled off and treated with ethyl ether and then with acetone to yield coarse crystals of Dye C.
- the coarse crystals are recrystallized from a mixed solvent of chloroform/ methanol to yield 550 mg of Dye C having a meltingpoint above 310 C and a k of 559 nm.
- Other sensitizing dyes can be obtained by a similar method to the process as mentioned above.
- the sensitizing dyes of the general formula (I) are used, in general.
- tion is effective for the spectral sensitization of any silver halide photographic emulsions. And, it can sensitize sufiiciently an emulsion containing a hydrophilic colloid other than gelatin, for example, agar collodion, water soluble cellulose derivatives, polyvinyl alcohol and other synthetic or natural hydrophilic polymers.
- a mixed silver halide emulsion such as silver iodobromide, chloroiodobromide, and the like is suitable.
- sensitizing dyes For the preparation of spectrally sensitized photographic emulsions according to this invention, it is enough to add the sensitizing dyes to a photographic emulsion in a common manner. In practice, it is convenient to add the dyes as a solution thereof in a suitable solvent such as methanol, ethanol, cellosolve etc., to the emulsion.
- a suitable solvent such as methanol, ethanol, cellosolve etc.
- the photographic emulsion according to this invention may be treated by a known method for hyperand The spectral sensitizing process according to this invenother super-sensitization.
- additives ' which are generally used in the art of photographic EXAMPLES
- silver halide photographic emulsions containing a combination of the sensitizing dyes of this invention were also prepared.
- emulsions were coated onto a cellulose triacetate film base, dried, exposed through a red filter (transmitting rays of a wavelength longer than 580 nm) and a blue filter (transmitting rays of a wavelength of 400 490 nm and having a maximum transmission at,
- Amount of Amount of sensitizing Senfiilizing Sensitized myse s l added' mu EX erimental Dyg (10' mol/kg Dye (10 mol/kg wave length Relative red Inherent Referred to 1&6.
- Example No. Flo. emuLsi n No. emulsion) Emulsion (nm) sensitivity sensitivityv in drawings A 4 AgBr/l 656 12s 94 Fig.3(8).
- AgBr/l 648 I00 AgBr/l 648 I25 I87 AgBr/I 648 I40 87 AgBr/l 662 50 93 3 AgBr/l 662 I00 90 3 C 4 2 1 AgBr/I 654 94 C 4 2 ,535. 3!!! .9, 199, 94
- AgBr/l 666 10 90 AgBr/l 634 13 87 AgBr/l 634 26 87 4 1 AgBr/I 652 120 96 AgBr/I 660 135 96 AgBr/l 600 16 1 93 Fi .,2(41. AgBr/l 600 313 93 5 AgBr/l 632 60 85 Fig. 2(5).
- the addition of a single sensitizing dye according to this invention reduces inherent sensitivity together with an increase of red sensitivity as the amount of dye added is increased.
- the combined use of the sensitizing dyes provides a higher red sensitivity than in the single use of the corresponding sensitizing dye alone.
- the effect of the combination of said sensitizing dyes is not injured by the further addition of a green sensitizing l0 dye thereto, e.g. the combined use of green sensitizing dye (i) or (ii) with the combination of the sensitizing dyes according to this invention.
- the said green sensitizing dyes have the following chemical structures, but they are not restricted only to these sensitizing dyes.
- Dye ll wherein R and R each represents a lower alkyl group; A, represents a lower alkyl group or an aryl group; 2;, and Z each represents an atomic group necessary to complete a benzothiazole, benzoselenazole or B naph-. thothiazole nucleus; X, represents an anion; and m is Qorbmkei wh an szrmv ssql saltisf tmcd- 2.
- R and R each represents a lower alkyl group
- A represents a lower alkyl group
- z rep res ents an atomic group necessary to complete a benzothiazole or benzoselenazole nucleus
- Z represents a sulfur or a selemum atom
- X 1- represents an anion, and n is 0 or 1
- the silver halide photographic emulsion of claim 1 further containing at least one green sensitizing cyanine dye selected from the group consisting of 2,2- yan1ne and thia-2 -c yanine 4.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45083653A JPS4842498B1 (enrdf_load_stackoverflow) | 1970-09-24 | 1970-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3770449A true US3770449A (en) | 1973-11-06 |
Family
ID=13808395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00183492A Expired - Lifetime US3770449A (en) | 1970-09-24 | 1971-09-24 | Spectrally sensitized silver halide photographic emulsion |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3770449A (enrdf_load_stackoverflow) |
| JP (1) | JPS4842498B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2147893C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2108455A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1355853A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3918979A (en) * | 1970-09-21 | 1975-11-11 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US5316904A (en) * | 1992-11-19 | 1994-05-31 | Eastman Kodak Company | Amide substituted dye compounds and silver halide photographic elements containing such dyes |
| US5354651A (en) * | 1992-11-19 | 1994-10-11 | Eastman Kodak Company | Hydroxyarylacyl dye compounds and silver halide photographic elements containing such dyes |
| US5492802A (en) * | 1992-11-19 | 1996-02-20 | Eastman Kodak Company | Dye compounds and photographic elements containing such dyes |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2066966A (en) * | 1931-02-07 | 1937-01-05 | Agfa Ansco Corp | Manufacture of light sensitive materials |
| US2066967A (en) * | 1931-02-07 | 1937-01-05 | Agfa Ansco Corp | Dyes of the cyanine series |
| US3679428A (en) * | 1969-07-23 | 1972-07-25 | Fuji Photo Film Co Ltd | Spectrally sensitized photographic emulsions |
-
1970
- 1970-09-24 JP JP45083653A patent/JPS4842498B1/ja active Pending
-
1971
- 1971-09-23 GB GB4452071A patent/GB1355853A/en not_active Expired
- 1971-09-23 FR FR7134240A patent/FR2108455A5/fr not_active Expired
- 1971-09-24 DE DE2147893A patent/DE2147893C3/de not_active Expired
- 1971-09-24 US US00183492A patent/US3770449A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2066966A (en) * | 1931-02-07 | 1937-01-05 | Agfa Ansco Corp | Manufacture of light sensitive materials |
| US2066967A (en) * | 1931-02-07 | 1937-01-05 | Agfa Ansco Corp | Dyes of the cyanine series |
| US3679428A (en) * | 1969-07-23 | 1972-07-25 | Fuji Photo Film Co Ltd | Spectrally sensitized photographic emulsions |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3918979A (en) * | 1970-09-21 | 1975-11-11 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US5316904A (en) * | 1992-11-19 | 1994-05-31 | Eastman Kodak Company | Amide substituted dye compounds and silver halide photographic elements containing such dyes |
| US5354651A (en) * | 1992-11-19 | 1994-10-11 | Eastman Kodak Company | Hydroxyarylacyl dye compounds and silver halide photographic elements containing such dyes |
| US5492802A (en) * | 1992-11-19 | 1996-02-20 | Eastman Kodak Company | Dye compounds and photographic elements containing such dyes |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2147893A1 (de) | 1972-05-25 |
| FR2108455A5 (enrdf_load_stackoverflow) | 1972-05-19 |
| JPS4842498B1 (enrdf_load_stackoverflow) | 1973-12-13 |
| GB1355853A (en) | 1974-06-05 |
| DE2147893C3 (de) | 1974-12-12 |
| DE2147893B2 (de) | 1974-05-16 |
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