US3764340A - Spectrally sensitized silver halide photographic emulsion - Google Patents
Spectrally sensitized silver halide photographic emulsion Download PDFInfo
- Publication number
- US3764340A US3764340A US00183592A US3764340DA US3764340A US 3764340 A US3764340 A US 3764340A US 00183592 A US00183592 A US 00183592A US 3764340D A US3764340D A US 3764340DA US 3764340 A US3764340 A US 3764340A
- Authority
- US
- United States
- Prior art keywords
- dye
- silver halide
- photographic emulsion
- halide photographic
- sensitizing dyes
- 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
- -1 silver halide Chemical class 0.000 title abstract description 42
- 239000000839 emulsion Substances 0.000 title abstract description 38
- 229910052709 silver Inorganic materials 0.000 title abstract description 21
- 239000004332 silver Substances 0.000 title abstract description 21
- 239000000975 dye Substances 0.000 abstract description 65
- 230000001235 sensitizing effect Effects 0.000 abstract description 38
- 230000035945 sensitivity Effects 0.000 abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 206010070834 Sensitisation Diseases 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 5
- 230000008313 sensitization Effects 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000000586 desensitisation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NIPMJVLJVGQZRB-UHFFFAOYSA-N Cl[IH]Br Chemical compound Cl[IH]Br NIPMJVLJVGQZRB-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 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
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- This invention relates to a spectrally sensitized silver halide photographic emulsion, and more particularly 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.
- An object of this invention is to provide a silver halide photographic emulsion having a high red sensitivity within the spectrally sensitized wavelength region of 620-685 11m. and a small inherent desensitization by the combined use of two different types of sensitizing dyes.
- it aims at the improved red sensitivity of blackwhite sensitive material having a sensitive maximum in the vicinity of 630 nm. and the improved spectral sensitivity of black-White sensitive material having a sensitive maximum in a longer wavelength region, i.e. in the region of 640680 nm.
- R represents a lower alkyl group, e.g., methyl, ethyl, propyl, etc., alkenyl, e.g., vinyl, methyl, etc.
- R represents a sulfoalkyl group, e.g., 'y-sulfopropyl, -sulfobutyl, fi-sulfobutyl, etc.
- A represents a lower alkyl group, e.g., methyl, ethyl, etc., or an aryl group, e.g., phenyl, p-methoxyphenyl
- Z represents nonmetallic atoms re- 3,764,340 Patented Oct.
- P and Q represent hydrogen atoms or lower alkyl groups or an atomic group capable of being connected to each other to form a heterocyclic ring
- R and R each represents a lower alkyl group, e.g., methyl, ethyl, propyl, 'y-sulfopropyl, 'y-sulfobutyl, fi-sulfobutyl, fi-carboxybutyl, etc.;
- A represents a lower alkyl group, e.g., methyl, ethyl, etc., or an aryl group, e.g., phenyl;
- Z and 2 each represents nonmetallic atoms required to complete a benzothiazole, benzoselenazole or ,B-naphth'othiazole nucleus, which may be substituted by a halogen atom, e.g., chlorine, bromine atom, etc., a lower alkyl group, e.g
- the cyanine dyes of the general Formula I have a sensitized maximum peak in the range of 620-650 nm. and, compared with the sensitizing dyes of the general Formula II, a very small red sensitivity. Many cyanine dyes of the general Formula II have a sharp J-band and a high red sensitivity. It has been found that the combined use of said sensitizing dyes (I) and (II) having such features improves the red sensitivity of said sensitizing dye of (II), resulting in a silver halide photographic emulsion having a very small inherent densensitization.
- the combination of said sensitizng dye of (I) and mesomethylthiacarbocyanine among said sensitizng dye (II) is suitable to a black-white sensitive material having a sensitized maximum peak in the vicinity of 630 nm. and shows such eifect that has not been found in the previous art, said effect extending gradually the spectral sensitization region to the longer wavelength without a large shift of sensitive maximum peak.
- the combination use of a sensitizing dye of the general Formula I and a symmetrical fi-naphthothiacarbocyanine of the general Formula II has a peculiar effect: that is, the sensitized maximum peak may be selected voluntarily in the region of 620- 680 nm.
- the spectral sensitivity can be highly increased to maintain the red sensitivty at a high level. Said effect is not affected by using at the same time another sensitizer for improving the green sensitivity (for example, 2,2'-cyanine, thia-2-cyanine, etc.) or sensitizers having other spectral sensitization region.
- another sensitizer for improving the green sensitivity for example, 2,2'-cyanine, thia-2-cyanine, etc.
- sensitizers having other spectral sensitization region for example, 2,2'-cyanine, thia-2-cyanine, etc.
- FIGS. 14 show the sensitivities of the dyes described herein when compared with various control samples. A fuller understanding of the drawings can be had by referring to Table 2 and the specific examples reported therein.
- sensitizing dyes used in this invention are mentioned as follows, but said sensitizing dyes used in this invention are not restricted to these examples.
- Dye L The sensitizing dyes of the general Formulas I and II, which are used in this invention, can be synthesized by a known method. For example, by reference to U.S. Pat. No. 2,503,776 and German Pat. Nos. 929,080 asd 1,072,- 765, those skilled in the art can synthesize them readily.
- sensitizing dyes according to this invention can be similarly synthesized.
- the spectral sensitization process according to this invention is effective for the spectral sensitization of gelatin silver halide photographic emulsion. It can also sensitize sufficiently an emulsion containing hydrophilic colloid other than gelatin, e.g., agar collodion, watersoluble cellulose derivatives, polyvinyl alcohol or other synthetic or natural hydrophilic resins.
- a mixed silver halide emulsion such as silver iodobromide, chloroiodobromide, etc., are suitable.
- sensitizing dye of (I) and (II) it is possible to add said sensitizing dye of (I) and (II) to a photographic emulsion in a common manner.
- the dyes it is convenient to add the dyes as a solution in a suitable solvent such as methanol, ethanol, etc., to the emulsion.
- the sensitizing dyes (I) and (II) to be contained in the emulsion are used in an amount of 10- to 10- mol/mol of silver halide respectively and the molar ratio of both dyes may be varied within a wide range of from 9:1 to 1:9 corresponding to the etfect desired.
- the photographic emulsion according to this invention can be applied further with the hyperand other super-sensitization.
- additives which are generally used, for example, chemical sensitizer, stabilizer, toner, hardener, surface active agent, antifoggant, plasticizer, development accelerator, color developer and fluorescent brightening agent can be contained in the emulsion in a common manner.
- the photographic emulsion according to this invention can be coated on a suitable base, for example, glass, films of cellulose derivatives, films of synthetic resins, baryta paper or resin-coated paper in a common manner.
- a suitable base for example, glass, films of cellulose derivatives, films of synthetic resins, baryta paper or resin-coated paper in a common manner.
- Single sensitizing dye of (I) and (II) used in this invention each was added to a silver iodobromide emulsion (AgI:AgBr7:93 in mol percent) to prepare silver halide photographic emulsions.
- silver halide photographic emulsions containing the combination of said sensitizing dyes of (I) and (II) used in this invention were prepared. These emulsions were coated respectively on a cellulose triacetate film base, dried, then exposed through a yellow filter (a filter transmitting rays of longer wavelength than 580 nm.) and a blue filter (a filter transmitting rays of 400-490 nm. and having a maximum transmission at 450 nm.) to a daylight of 64 luxes (corresponding to 5,400 K.) and developed.
- the liquid developer one having the composition shown in Table 1 was used. 1
- the yellow and red sensitivity are each shown as the relative sensitivity to the sensitivity 100 of said sensitiziug dye H which is exposed in an amount of 4X16- mol/kg. emulsion through the yellow and red filter as mentioned above and the inherent sensitivity is shown as the relative sensitivity to the sensitivity 100 of original emulsion which is exposed through the blue filter.
- the green sensitizing dyes which may be used in combination with said sensitizing dye of (I) and (II) used in this invention are those having the follownig chemical structures, but they are not restricted only to these sensitizing dyes.
- R represents a lower alkyl or alkenyl group
- R represents a sulfoalkyl group
- A represents a lower alkyl, or aryl group
- Z represents a n'on'rnetallic atom required to complete a benzothiazole, benzoselenazole or B-naphthothiazole nucleus
- Z represents a sulfur or selenium atom
- B represents a phenyl
- P and Q each represents a hydrogen atom or a lower alkyl group or an atomic group capable of being connected to form a morpholine ring
- X represents an anion
- n is 0 or 1, n being 0 for the intermolecular salt
- A represents a lower alkyl or aryl group
- Z and Z each represents a nonmetallic atom required to complete a' benzothiazole, benzoselenazole or B-naphthothiazle nucleus
- X represents an anion
- m is 0 or 1
- m being 0 for the intermolecular salt.
- the sensitizing dye of the general Formula II is a member selected from the group consisting of:
- Anionic mi 6 (JHDaSOr 132KB 30 6.
- a photographic light-sensitive material compi'ising a layer containing the photographic emulsion as claimed in claim 1.
Landscapes
- 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)
- Plural Heterocyclic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45083656A JPS4842499B1 (OSRAM) | 1970-09-24 | 1970-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3764340A true US3764340A (en) | 1973-10-09 |
Family
ID=13808482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00183592A Expired - Lifetime US3764340A (en) | 1970-09-24 | 1971-09-24 | Spectrally sensitized silver halide photographic emulsion |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3764340A (OSRAM) |
| JP (1) | JPS4842499B1 (OSRAM) |
| DE (1) | DE2147888C3 (OSRAM) |
| FR (1) | FR2108527A5 (OSRAM) |
| GB (1) | GB1364918A (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179296A (en) * | 1975-12-29 | 1979-12-18 | Fuji Photo Film Co., Ltd. | 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 |
-
1970
- 1970-09-24 JP JP45083656A patent/JPS4842499B1/ja active Pending
-
1971
- 1971-09-23 GB GB4451971A patent/GB1364918A/en not_active Expired
- 1971-09-24 US US00183592A patent/US3764340A/en not_active Expired - Lifetime
- 1971-09-24 DE DE2147888A patent/DE2147888C3/de not_active Expired
- 1971-09-24 FR FR7134469A patent/FR2108527A5/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179296A (en) * | 1975-12-29 | 1979-12-18 | Fuji Photo Film Co., Ltd. | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2147888C3 (de) | 1974-10-31 |
| GB1364918A (en) | 1974-08-29 |
| FR2108527A5 (OSRAM) | 1972-05-19 |
| DE2147888A1 (de) | 1972-04-13 |
| DE2147888B2 (de) | 1974-04-04 |
| JPS4842499B1 (OSRAM) | 1973-12-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3617293A (en) | Photographic supersensitized silver halide emulsions | |
| US3666480A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US3615635A (en) | Silver halide photographic emulsion | |
| US3814609A (en) | Silver halide supersensitized photographic emulsions | |
| US3632349A (en) | Silver halide supersensitized photographic emulsion | |
| US3348949A (en) | Photographic light-sensitive materials | |
| US3764340A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US3573920A (en) | Fine grain silver halide emulsions containing novel dye combinations | |
| US3922170A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US2158882A (en) | Photographic emulsion | |
| US3808009A (en) | Light-sensitive super-sensitized silver halide photographic emulsions | |
| US3681080A (en) | Silver halide photographic emulsion | |
| US3988513A (en) | Silver halide emulsions for recording electron rays | |
| US3933510A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US3694217A (en) | Silver halide photographic emulsion | |
| US3971664A (en) | Fine grain silver halide emulsions with polyheteronuclear sensitizing dyes | |
| US3770449A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US2159565A (en) | Photographic emulsion | |
| US2848329A (en) | Supersensitization with bis-heterocyclic bases | |
| US3698910A (en) | Light-sensitive silver halide photographic material | |
| US4039335A (en) | Photographic silver halide emulsions | |
| US3705809A (en) | Silver halide supersensitized photographic emulsion | |
| US3769026A (en) | Spectrally sensitized silver halide photographic emulsion | |
| US2852385A (en) | Supersensitization of photographic emulsions | |
| US2398778A (en) | Sensitized photographic emulsion |