US2586164A - Photographic emulsions containing symmetrical tetranuclear dyestuffs - Google Patents
Photographic emulsions containing symmetrical tetranuclear dyestuffs Download PDFInfo
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- US2586164A US2586164A US193285A US19328550A US2586164A US 2586164 A US2586164 A US 2586164A US 193285 A US193285 A US 193285A US 19328550 A US19328550 A US 19328550A US 2586164 A US2586164 A US 2586164A
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- dyestuffs
- tetranuclear
- silver halide
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- 239000000839 emulsion Substances 0.000 title claims description 17
- -1 SILVER HALIDE Chemical class 0.000 claims description 22
- 229910052709 silver Inorganic materials 0.000 claims description 18
- 239000004332 silver Substances 0.000 claims description 18
- 239000000975 dye Substances 0.000 claims description 14
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
- 230000001235 sensitizing effect Effects 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical class O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QNJHGPHQXHFAHA-UHFFFAOYSA-N 4-(1,3-thiazol-4-yl)-1,3-thiazole Chemical compound S1C=NC(C=2N=CSC=2)=C1 QNJHGPHQXHFAHA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GUWWTYPDEOUCTR-UHFFFAOYSA-N 2,2-dimethyl-4-(1,3-thiazol-4-yl)-3H-1,3-thiazole Chemical compound CC1(SC=C(N1)C=1N=CSC1)C GUWWTYPDEOUCTR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- KVTHPKXDLVYNCH-UHFFFAOYSA-N 2-iodoethylbenzene Chemical compound ICCC1=CC=CC=C1 KVTHPKXDLVYNCH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- DVRWEKGUWZINTQ-UHFFFAOYSA-N 3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound O=C1CSC(=S)N1C1=CC=CC=C1 DVRWEKGUWZINTQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- G03C1/22—Methine and polymethine dyes with an even number of CH groups
Definitions
- This invention relates to gelatino silver halide emulsions, "and particularly to photographic emulsions sensitized by means of new symmetrical tetranuclear dyestuffs in which the central nucleus, 4,4-bithiazole is linked to two-N-substituted rhodanine nuclei by a dimethine chain.
- sensitizing dyes operate bydyeing the silver halide grain. To do this, they must be adsorbed to the silver halide. If they are displaced from the silver halide grains, they lose their efiectiveness as sensitizers. It is also known that many color formers used in color photography have greater aifinity for silver halides than the sensitizers, and act to displace the same from the silver halide grains. One must, therefore, select a sensitizer which will not be so displaced.
- An object of the present invention is to provide photographic gelatino silver halide emulsions with new symmetrical tetranuclear dyestuffs in which the central nucleus, 4,4'-bithiazole, is linked to two N-substituted rhodanine nuclei by a dimethine chain.
- a further object is to provide such dyestuffs which are free from the disadvantages noted above.
- This invention is predicted upon the discovery that symmetrical tetranuclear dyestuffs, in which the central nucleus, 4,4'-bithiazole, linked to two N-substituted rhodanine nuclei by a dimethine chain, are not only sensitizers for orthochromatic and panchromatic film emulsions, but are also compatible with color coupling components, being unaffected by the presence of color coupling components and exhibiting the property of non-.'- migration from the layer in which they are in-: corporated. In the latter combination, the sensitizing action of the dyestuffs is not impaired or diminished.
- An additional advantage of these dyestuffs is their ability to remain fixed in the layer in which they are originally deposited.
- R represents an alkyl group, e. g., methyl, ethyl, propyl, butyl, etc., allyl and phenyl
- R1 represents an alkyl or aralkyl group, e. g., methyl, ethyl, propyl, isopropyl, butyl, etc., benzyl, phenethyl, and the like.
- the process of preparing the above dyes comprises heating, preferably, under reflux conditions, with or without atertiary base, an alcoholic solution containing one mol of a di-quaternary cyclammonium salt of 2,2-dimethyl-4,4'-bithiazole and two mols of a rhodanine intermediate having a reactive acetanilido group linked to a monomethine chain adjacent to a keto group'of such intermediate.
- the rhodanineintermedi'ates are described in United States Patent No. 2,186,608.
- cyclammonium salts of- 2,2- dimethyl-4,4-bithiazole utilized in the condensation' reaction are characterized by the following general formula:
- the quaternization of the 2,2-dimethyl4,4'- bithiazole is eil'ectuated by fusion with an alkylatihg' agent; e. g'., an alkyl or aralkyl halide or by heating'thebase with an alkylating agent, e. g., an alkyloraralkylhalide in a sealed tube in a water bath under increased pressure in the usual manher.
- the alkylating agent employed may be methyl or ethyl iodide,.dimethyl sulfate, methyl p-toluen'esulfonate, phenethyl iodide, and the like.
- solvent-diluents employed in the preparation of the new dyes of the'present invention employing: methyl; ethyl; propyl, isopropyl, butyl, benzyl, furfuryl alcohol and the like.
- Triethylamine, tributylamine and the like are representative-of the tertiary bases which I may use.
- Example I The melting pointof the crude Example I was repeated with the exception 0 that 0.33 gram of 3-ethyl-5-acetanilidomethylenerhodanine was substituted for 0.35 gram of 3- allyl-5-acetanilidomethylenerhodanine.
- a tetranucle'ar merocyanine dyestuff was obtained which has approximately the same sensitizing properties as the dyestufl of Example I.
- Example I was repeated with the exception that 15 0.4 gram of S-phenyl-E-acetanilidomethylenerhodanine was substituted for 0.35 gram of 3- allyl-5-acetanilidomethylenerhodanine.
- the dyestufi obtained has approximately the same sensitizing characteristics as the dyestufi of Example I.
- the diagrammatic spectrogram constituting the accompanying drawing illustrates the regions of the spectrum to which the symmetrical tetranuclear merocyanine dyestuffs will sensitize a gelatino silver halide emulsion containing 45% of silver halide and the extent of the sensitization at various Wavelengths.
- the single figure of the accompanying drawing illustrates the sensitizing properties of the dyes prepared in accordance with Examples I to III, respectively.
- a photographic gelatino silver halide emulsion which contains a dyestuif of the following structure:
- a photographic gelatino silver halide emulsion which contains a dyestuff of the following structure:
- a photographic gelatino silver halide emulsion which contains a dyestufi of the following structure:
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- 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)
- Plural Heterocyclic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Feb. 19, 1952 L. c. HENSLEY 2,586,164
PHOTOGRAFHIC EMULSIONS CONTAINING SYMMETRICAL TETRANUCLEAR DYESTUFFS Filed Oct. 51, 1950 INVENTOR Lee C. Hensley B LBW Patented Feb. 19, 1952 PHOTOGRAPHIC EMULSIONS CONTAIN- ING SYMMETRICAL TETRANUCLEAR DYESTUFFS Lee C. Hensley, Binghamton, N. Y., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware Application October 31, 1950, Serial No. 193,285
. 4 Claims. 1 s
This invention relates to gelatino silver halide emulsions, "and particularly to photographic emulsions sensitized by means of new symmetrical tetranuclear dyestuffs in which the central nucleus, 4,4-bithiazole is linked to two-N-substituted rhodanine nuclei by a dimethine chain.
The use of sensitizing dyes, particularly in multilayer color film, poses many problems. It is known that sensitizing dyes operate bydyeing the silver halide grain. To do this, they must be adsorbed to the silver halide. If they are displaced from the silver halide grains, they lose their efiectiveness as sensitizers. It is also known that many color formers used in color photography have greater aifinity for silver halides than the sensitizers, and act to displace the same from the silver halide grains. One must, therefore, select a sensitizer which will not be so displaced.
Another-problem arises as regards the migration of the sensitizers from one emulsion to another. Where this ensues, color distortion is the inevitable result. Many proposals have been made dealing with the anchoring of compounds placement from silver halide grains by color formers, and (35 the ability to resist diffusion from one sensitized emulsion to another.
Efforts which satisfy the last prerequisite, unfortunately, often lead to compounds which will not meet the first two tests. Thus, it is known that thesensitizing power of cyanine dyes varies with the substituent on the cyanine N-atoms. Where this substituent is alkyl, the power decreases as the chain length increases. Hence, if a long alkyl chain be used to anchor the dye in the emulsion, we end-up with a product of little or no sensitizing power. The use of other expedients to anchor the dye, on the other hand, often gives products incapable of withstanding the displacement action of color formers insofar 2 as the silver halide grains are concerned. It is thus manifest that the provision of sensitizers having the necessary prerequisite is a dlfllcult problem, to say the least.
It is known that many cyanine dyes sensitize photographic silver halide emulsions to high red sensitivity. Most of these dyes, however, are not suitable for sensitizing silver halide emulsions containing color coupling components. This is thought to be due to a physical displacement which the sensitizing dye undergoes when color coupling components are added. That is, the sensitizer is adsorbed to the surface of the silver halide grain, and then, with addition of color coupling component, is displaced therefrom. An object of the present invention is to provide photographic gelatino silver halide emulsions with new symmetrical tetranuclear dyestuffs in which the central nucleus, 4,4'-bithiazole, is linked to two N-substituted rhodanine nuclei by a dimethine chain.
A further object is to provide such dyestuffs which are free from the disadvantages noted above. A
Other objects and advantages of this invention will become apparent by reference to the following specification in which its preferred details and embodiments are described.
This invention is predicted upon the discovery that symmetrical tetranuclear dyestuffs, in which the central nucleus, 4,4'-bithiazole, linked to two N-substituted rhodanine nuclei by a dimethine chain, are not only sensitizers for orthochromatic and panchromatic film emulsions, but are also compatible with color coupling components, being unaffected by the presence of color coupling components and exhibiting the property of non-.'- migration from the layer in which they are in-: corporated. In the latter combination, the sensitizing action of the dyestuffs is not impaired or diminished. An additional advantage of these dyestuffs is their ability to remain fixed in the layer in which they are originally deposited.
The symmetrical tetranuclear merocyanine dyestuffs fulfilling the above advantages are characterized by the following general formula:
wherein R represents an alkyl group, e. g., methyl, ethyl, propyl, butyl, etc., allyl and phenyl, and R1 represents an alkyl or aralkyl group, e. g., methyl, ethyl, propyl, isopropyl, butyl, etc., benzyl, phenethyl, and the like.
The process of preparing the above dyes comprises heating, preferably, under reflux conditions, with or without atertiary base, an alcoholic solution containing one mol of a di-quaternary cyclammonium salt of 2,2-dimethyl-4,4'-bithiazole and two mols of a rhodanine intermediate having a reactive acetanilido group linked to a monomethine chain adjacent to a keto group'of such intermediate. The rhodanineintermedi'ates are described in United States Patent No. 2,186,608.
As illustrative examples of such rho'danine intermediates, reference is made to:
-acetanilidomethylene-3-methylrhodanine S-acetanilidomethylene-3-ethylrhodanine 5-acetanilidomethylene-3-allylrhodanine 5Facetanilidomethylene-3 propylrhodanine 5-acetanilidomethylene 3 -phenylrhodanine 'Ifhe di-quaternary. cyclammonium salts of- 2,2- dimethyl-4,4-bithiazole utilized in the condensation' reaction are characterized by the following general formula:
S? S CH HC wherein R1 has-the same value as above and X represents anani'onic acid. radical, e. g., Cl, Br, I, C104, SO4CH3, SO4CiH5,- SOsCsHiCHs, and the product was 109-111 C. After crystallizing from petroleum ether (B. P. 60-75 0.), the melting point was 117 C. and the yield of the product was 13.6 grams.
One gram of 1,4-dibromobutane-2,3 and 0.63 gram of thioacetamide were dissolved in 20 cc. of absolute methanol and warmed for 10 minutes on the steam bath. The mixture. (2.. solid had separated) was poured'intolOOcc'. of'water. The aqueous mixture was made acid with diluted hydrochloric acid and filtered. Upon neutralization. a brownish solid appeared in the filtrate. This solid. was filtered off and recrystallized from methanol and had a melting point of 165 C.
The quaternization of the 2,2-dimethyl4,4'- bithiazole is eil'ectuated by fusion with an alkylatihg' agent; e. g'., an alkyl or aralkyl halide or by heating'thebase with an alkylating agent, e. g., an alkyloraralkylhalide in a sealed tube in a water bath under increased pressure in the usual manher. The alkylating agent employed may be methyl or ethyl iodide,.dimethyl sulfate, methyl p-toluen'esulfonate, phenethyl iodide, and the like.
As solvent-diluents employed in the preparation of the new dyes of the'present invention,- the following alcohols may be employed: methyl; ethyl; propyl, isopropyl, butyl, benzyl, furfuryl alcohol and the like. Triethylamine, tributylamine and the like are representative-of the tertiary bases which I may use.
The following examples describe in detail the methods of accomplishing the above objects, but it is to be understood that they are inserted merely for the purpose of illustration and are not to be construed as limiting the scopeoftheinvention.
Emample' I like. and are obtained by quaternizing 2,2'-dimetli'yl.-4',4"-bithiazole characterized by the following formula:
The"2,'2" -dimethyl=4,4'!-bithiazo1e is prepared in the following manner:
Eight: and six-tenths grams (0.1: mol) of but'anedione-ZB (diacetyD in 35. cc. of carbon disulfide were treatedxdropwisewith stirring; with asolutionof 101600. of 'bromin'e'in 20 cc. of carbon disulfide at the boiling point of the carbon disulfide. The addition was completedin 3 hours. The. stirring. andrheating were continued another 2 hours. After cooling, the; carbon disulfide was decanted irom the solid. which had separated. The crystals were washed with petroleum ether (P. B. (so-75 0.). The melting pointof the crude Example I was repeated with the exception 0 that 0.33 gram of 3-ethyl-5-acetanilidomethylenerhodanine was substituted for 0.35 gram of 3- allyl-5-acetanilidomethylenerhodanine. A tetranucle'ar merocyanine dyestuff was obtained which has approximately the same sensitizing properties as the dyestufl of Example I.
Example III Li s=d =0 \l Example I was repeated with the exception that 15 0.4 gram of S-phenyl-E-acetanilidomethylenerhodanine was substituted for 0.35 gram of 3- allyl-5-acetanilidomethylenerhodanine. The dyestufi obtained has approximately the same sensitizing characteristics as the dyestufi of Example I.
The diagrammatic spectrogram constituting the accompanying drawing illustrates the regions of the spectrum to which the symmetrical tetranuclear merocyanine dyestuffs will sensitize a gelatino silver halide emulsion containing 45% of silver halide and the extent of the sensitization at various Wavelengths. The single figure of the accompanying drawing illustrates the sensitizing properties of the dyes prepared in accordance with Examples I to III, respectively.
illustrations, or to the specific details given therein, but is capable of variations and modifications s s ESE O=CH CH= S \N/ \N/ 0= \N/ J=s wherein R represents a member selected from the class consisting of alkyl, allyl, and phenyl groups, and R1 represents a member selected from the class consisting of alkyl and aralkyl groups.
2. A photographic gelatino silver halide emulsion which contains a dyestuif of the following structure:
This application is a continuation-in-part of my application Serial No. 92,585, filed May 11, 1949, now abandoned, which was a division of application Serial No. 75,751, filed February 10,
3. A photographic gelatino silver halide emulsion which contains a dyestuff of the following structure:
1949, now abandoned. The sensitizing dyestufis. per se, are claimed in copending application Serial No. 189,487, filed October 10, 195-0, now Patent No. 2,553,503.
4. A photographic gelatino silver halide emulsion which contains a dyestufi of the following structure:
an. an.
While there have been pointed out above certain preferred embodiments of the invention, the same is not limited to the foregoing examples,
LEE C. HENSLEY.
No references cited.
Claims (1)
1. A PHOTOGRAPHIC GELATINO SILVER HALIDE EMULSION CONTAINING A SYMMETRICAL TETRANUCLEAR MEROCYANINE DYESTUFF CHARACTERIZED BY THE FOLLOWING GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193285A US2586164A (en) | 1950-10-31 | 1950-10-31 | Photographic emulsions containing symmetrical tetranuclear dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193285A US2586164A (en) | 1950-10-31 | 1950-10-31 | Photographic emulsions containing symmetrical tetranuclear dyestuffs |
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| US2586164A true US2586164A (en) | 1952-02-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| US193285A Expired - Lifetime US2586164A (en) | 1950-10-31 | 1950-10-31 | Photographic emulsions containing symmetrical tetranuclear dyestuffs |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148982A (en) * | 1960-04-11 | 1964-09-15 | Gevaert Photo Prod Nv | Electrophotographic process utilizing organic photoconductors |
| US3194805A (en) * | 1960-09-02 | 1965-07-13 | Eastman Kodak Co | Merocyanine and holopolar dyes containing arylene-chain substitution |
-
1950
- 1950-10-31 US US193285A patent/US2586164A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148982A (en) * | 1960-04-11 | 1964-09-15 | Gevaert Photo Prod Nv | Electrophotographic process utilizing organic photoconductors |
| US3194805A (en) * | 1960-09-02 | 1965-07-13 | Eastman Kodak Co | Merocyanine and holopolar dyes containing arylene-chain substitution |
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