US3769024A - Light-sensitive silver halide photographic material with sensitizing dye combination - Google Patents
Light-sensitive silver halide photographic material with sensitizing dye combination Download PDFInfo
- Publication number
- US3769024A US3769024A US00163100A US3769024DA US3769024A US 3769024 A US3769024 A US 3769024A US 00163100 A US00163100 A US 00163100A US 3769024D A US3769024D A US 3769024DA US 3769024 A US3769024 A US 3769024A
- Authority
- US
- United States
- Prior art keywords
- alkyl group
- light
- silver halide
- group
- lower alkyl
- 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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- 239000000463 material Substances 0.000 title claims abstract description 43
- -1 silver halide Chemical class 0.000 title claims abstract description 38
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 37
- 239000004332 silver Substances 0.000 title claims abstract description 37
- 230000001235 sensitizing effect Effects 0.000 title description 22
- 150000001875 compounds Chemical class 0.000 claims description 62
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 abstract description 43
- 125000000217 alkyl group Chemical group 0.000 abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 20
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 abstract description 8
- 125000005843 halogen group Chemical group 0.000 abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 4
- 150000001340 alkali metals Chemical group 0.000 abstract description 4
- 150000001450 anions Chemical group 0.000 abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract description 4
- 229910052711 selenium Inorganic materials 0.000 abstract description 4
- 125000004964 sulfoalkyl group Chemical group 0.000 abstract description 4
- 150000007530 organic bases Chemical group 0.000 abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 28
- 206010070834 Sensitisation Diseases 0.000 description 13
- 230000008313 sensitization Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- 206010034960 Photophobia Diseases 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 208000013469 light sensitivity Diseases 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000005070 ripening Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 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 2
- 239000002585 base Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- NFQCZOCWVMXBJE-UHFFFAOYSA-N 3-[[2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetyl]amino]-n-[3-oxo-2-(2,4,6-trichlorophenyl)-1h-pyrazol-5-yl]benzamide Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC=C1OCC(=O)NC1=CC=CC(C(=O)NC=2NN(C(=O)C=2)C=2C(=CC(Cl)=CC=2Cl)Cl)=C1 NFQCZOCWVMXBJE-UHFFFAOYSA-N 0.000 description 1
- 101000685083 Centruroides infamatus Beta-toxin Cii1 Proteins 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- ZUIVNYGZFPOXFW-UHFFFAOYSA-N chembl1717603 Chemical compound N1=C(C)C=C(O)N2N=CN=C21 ZUIVNYGZFPOXFW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 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 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- ABSTRACT Photographic materials of improved green sensitivity containing a light-sensitive silver halide emulsion and including, in combination, at least one monomethinecyanine dye of the general formula,
- Y is a hydrogen atom, a lower alkyl group or a lower alkoxy group
- Z is S or Se
- V is a hydrogen atom or a lower alkyl group
- R is a lower alkyl group or a substituted alkyl group
- R is a sulfoalkyl group or a carboxyalkyl group
- X is an anion
- m is zero or 1, and at least one oxacarbocyanine dye of the general formula
- Y is a hydrogen atom or a lower alkyl group
- Y is a hydrogen atom, a lower alkyl group, a lower alkoxyl group, a halogen atom or a phenyl group
- W is a halogen atom or a phenyl group
- R is a lower alkyl group
- M is a hydrogen atom, an alkali metal atom or H.Q (where Q is an organic base); and n and n are individually 2, 3 or 4. Lower fog levels are also noted.
- Emulsions are detailed as well as materials utilizing such emulsions.
- This invention relates to a light-sensitive silver halide photographic material containing a specific combination of sensitizing dyes. More particularly, the invention pertains to a light-sensitive silver halide photographic material characterized by containing in the light-sensitive silver halide photographic emulsion a combination comprising at least one compound of the below-mentioned general formula (I) and at least one compound of the below-mentioned general formula (ll).
- Y is a hydrogen atom or a lower alkyl group
- Y is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a phenyl group
- W is a halogen atom or a phenyl group
- R is a lower alkyl group
- M is a hydrogen atom, an alkali metal atom or H.Q (where Q is an organic base); and n and n are individually 2, 3 or 4.
- the combination is desired to provide a high green-sensitivity and a spectral sensitization zone necessary for the attainment of the best color producibility as a light-sensitive 'color photographic material. Further, the combination is required to be such that even when used together with a magenta coupler, i.e., a magenta color-forming agent which couples with the oxidation product of a color developer of the pphenylenediamine type to form a color image, the combination should not bring about any degradation of green sensitivity or desensitization due to interaction with the magenta coupler.
- a magenta coupler i.e., a magenta color-forming agent which couples with the oxidation product of a color developer of the pphenylenediamine type to form a color image
- all the combinations used in the prior art super-sensitization have some of the above-mentioned drawbacks, and have not been satisfactory.
- sensitizing dyes of the general formulas (l) and (II) are ortho-type sensitizing dyes;
- the compound of the formula (I) when used singly, is a green-sensitive sensitizing dye showing the maximum wavelength of color sensitization in a short wavelength.
- the compound of the formula (ll) is a green-sensitive sensitizing dye showing the maximum wavelength of color sensitization in a long wavelength region (550 mp. 560 mp).
- these compounds are used independently, therefore, it is impossible to obtain a green-sensitive silver halide emulsion which sufficiently sensitizes in the required wavelength region.
- the long wavelength portion in the green-sensitive region is reinforced with a short wavelength portion, there are attained not only a high green sensitivity but also a green sensitization having a fresh color-sensitization maximum which cannot be exhibited if the compounds are used singly.
- the specific combination of sensitizing dyes according to the present invention is used, the sensitizing dyes necessary in. the multi-layer type color photography can be prevented from diffusion into other layers. Such effect is valuable in accomplishing a faithful color reproduction in color photography.
- Examples of the compounds of the general formula JzHs N @tlia Examples of the compounds of the general formula A light-sensitive photographic material according to the present invention, which has been supersensitized by incorporation of a specific combination of the above mentioned compounds, has such excellent properties as mentioned previously, and the combination of the compounds in accordance with the present invention can impart an ideal green sensitivity to silver halide emulsions.
- the combination of said compounds is effective as a markedly excellent spectral sensitizer for high sensitivity green-sensitivephotographic materials, particularly for green-sensitive emulsions of color photographic materials, according to application purposes.
- the combination is applicable to, for example, ordinary black-and-white photographic materials, various light-sensitive materials of the image transfer type, and color photographic materials of the type containing coloring dyes to be treated according to silver-bleaching method.
- the distribution of spectral sensitization maxima of the silver halide emulsion according to the present invention is variable depending on the kinds and proportions of the sensitizing dyes of the general formulas (l) and (Il). These compounds may be added to a silver halide emulsion after dissolving them either singly or in combination in an optionally water-miscible organic solvent such as methanol or ethanol.
- the time of addition of these sensitizing dyes to a silver halide photographic emulsion may be at any stage during the preparation of the emulsion, but is preferably immediately after, completion of the second ripening, in general.
- the amounts of the compounds to be added vary depending on the kinds of the compounds and of the silver halide, emulsion. Ordinarily, however, the total amount of the compounds of thegeneral formulas (l) and (II) is variable within a wide range from 1 to 200 mg. per kg. of the silver halide emulsion. In this case,
- the ratio of the compound (I) to the compound (ll) is preferably in the range from 1 to 5 l by weight.
- the emulsion used in the present invention may have been incorporated with a noble metal sensitizer, a sulfur sensitizer or a polyalkylene oxide type compound. Further, the emulsion may have, if necessary, been spectrally sensitized by using the said compounds together with another sensitizing dye .such as, for example, a cyanine or merocyanine dye. In addition, the emulsion may have been incorporated according to an ordinary procedure with such photographic additives as stabilizer, surfactant, hardener, etc.
- the green-sensitive emulsion for color photographic material used in the present invention may have further been incorporated with magenta couplers which develop colors by reaction of a p-phenylenediamine type color developer, and which have nuclei as, for example pyrazolone and imidazolone nuclei.
- magenta couplers which develop colors by reaction of a p-phenylenediamine type color developer, and which have nuclei as, for example pyrazolone and imidazolone nuclei.
- These couplers may be any of oleophilic or hydrophilic couplers having in the active methylene or methine portions substituents capable of being released by color development reaction, or diffusion-preventing groups or water solubilizing groups.
- the support used to prepare the lightsensitive material of the present invention may be any of paper, and cellulose triacetate or polyester and the like natural and synthetic high molecular weight films.
- Example 1 A high speed silver iodobromide emulsion containing 5 mole percent of silver iodide which has been treated with a gelatin coagulant (Japanese Patent Publication No. 16,086/60) was subjected to second ripening according to gold sensitization and sulfur sensitization methods, and then divided into several portions. Each divided emulsion was incorporated with a methanol solution of each of or a mixture of the sensitizing dyes set forth in Table 1. Subsequently, the emulsion was allowed to stand at about 40 C. for 20 minutes to stabilize the color stabilizing action thereof, incorporated with given amounts of a stabilizer, a hardener and a coating aid, coated on a film base and then dried to obtain a green-sensitive photographic material.
- a gelatin coagulant Japanese Patent Publication No. 16,086/60
- Example 2 A high speed silver iodobromide emulsion for negatives, which had been adjusted to the optimum sensitivity according to gold sensitization and sulfur sensitization, was divided into several portions each 1 kg. in weight. Each divided emulsion was incorporated with a combination of, 0.1 percent methanol solutions of the individual compounds set forth in Table 2.
- 1-(2,4,6- trichlorophenyl)-3-( 3-( 2,4-di-tert-amylphenoxyacetamido)-benzamido)-5-pyrazolone as a magenta coupler was dissolved at an elevated temperature in a mixed solvent comprising di-n-butyl phthalate and ethyl acetate, and then dispersed in a gelatin solution by use of sodium alkylbenzenesulfonate, and a given amount of the resulting dispersion was added to the emulsion. Subsequently, the emulsion was incorporated with a hardener and a coating aid and then adjusted to pH 6.8 to prepare a green-sensitive color photographic emulsion.
- This emulsion was uniformly coated on a cellulose triacetate film to a dry thickness of 5 p. to obtain a sample.
- the thus obtained samples were exposed in the same manner as in Example 1 and then subjected to sensitometry.
- the composition of the color developer used in the sensitometry was as follows:
- the light-sensitive silver halide photographic materials of the present invention are excellent green-sensitive color photographic materials which are not deteriorated in optical sensitizing property and less in residual color even when present together with a magenta coupler.
- Example 3 I A silver chlorobromide emulsion for photographic positives, containing 20 mole percent of silver bromide silver halide emulsion a combination comprising at least one monomethinecyanine dye of the formula,
- Y is a hydrogen atom, a lower alkyl group or a lower alkoxy group
- Z is S or Se
- V is a hydrogen atom or a lower alkyl group
- R is a lower alkyl group which may contain a sulfo or hydroxy group
- R is a sulfoalkyl group or a carboxyalkyl group having one to four car bon atoms
- X is an anion
- m is zero or one, and at least one oxacarbocyanine dye of the formula
- l-(2,4,6-trichlorophenyl)-3-(3- dodecyl-succinimidobenzamido)-5-pyrazolone as a magenta coupler was dissolved at an elevated temperature in a mixed solvent comprising di-n-butyl phthalate and ethyl acetate, and then dispersed in a gelatin solution by use of sodium alkylbenzenesulfonate, and a given amount of the resulting dispersion was added to the emulsion. Subsequently, the emulsion was incorporated with a hardener and a coating aid, coated on ,a film base and'then dried to prepare a sample.
- a light-sensitive silver halide photographic material characterized by containing in the light-sensitive halogen atom or a phenyl group; R is a lower alkyl group; M is a hydrogen atom or an alkali metal atom; and n, and n are individually 2, 3 or 4.
- a light-sensitive silver halide photographic material wherein the compound of said formula (I) is one member selected from the group CH; C O O H l Call-Is (wins a 2H4 H) N drncmooori 1 l CHzCHzOH (+)N H300 S B and and the compound of said formula (II) is one member selected from the group consisting of 3.
- a light-sensitive silver halide photographic material according to claim 2, wherein the exemplified compound (2) and the exemplified compound (10) are used in combination.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45061738A JPS4841205B1 (enrdf_load_stackoverflow) | 1970-07-16 | 1970-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3769024A true US3769024A (en) | 1973-10-30 |
Family
ID=13179819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00163100A Expired - Lifetime US3769024A (en) | 1970-07-16 | 1971-07-15 | Light-sensitive silver halide photographic material with sensitizing dye combination |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3769024A (enrdf_load_stackoverflow) |
| JP (1) | JPS4841205B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2135413A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1318154A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3861920A (en) * | 1974-01-02 | 1975-01-21 | Polaroid Corp | Super-sensitizing dye combination in silver halide emulsions |
| US3933510A (en) * | 1972-09-04 | 1976-01-20 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| US3953215A (en) * | 1973-07-16 | 1976-04-27 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsions |
| US4940657A (en) * | 1988-01-21 | 1990-07-10 | Mitsubishi Paper Mills Limited | Photographic spectral sensitizing dye |
| USH899H (en) | 1986-03-25 | 1991-03-05 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic material feasible for high speed |
| US5077183A (en) * | 1987-12-24 | 1991-12-31 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material and a process for the preparation of a photographic silver halide emulsion |
| US5348849A (en) * | 1990-10-26 | 1994-09-20 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| CN102702769A (zh) * | 2012-06-20 | 2012-10-03 | 大连理工大学 | 一类绿光荧光菁染料、制备方法及其应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52103812U (enrdf_load_stackoverflow) * | 1976-02-04 | 1977-08-06 | ||
| JPS59173183U (ja) * | 1983-05-09 | 1984-11-19 | 東洋紙業株式会社 | デイスク収納ケ−ス |
| US5658751A (en) * | 1993-04-13 | 1997-08-19 | Molecular Probes, Inc. | Substituted unsymmetrical cyanine dyes with selected permeability |
| US7776529B2 (en) | 2003-12-05 | 2010-08-17 | Life Technologies Corporation | Methine-substituted cyanine dye compounds |
| WO2006124816A1 (en) | 2005-05-11 | 2006-11-23 | Molecular Probes, Inc. | Fluorescent chemical compounds having high selectivity for double stranded dna, and methods for their use |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2132866A (en) * | 1937-03-29 | 1938-10-11 | Eastman Kodak Co | Photographic emulsion |
| US3580724A (en) * | 1968-06-04 | 1971-05-25 | Konishiroku Photo Ind | Light-sensitive supersensitized silver halide color photographic emulsions |
| US3615634A (en) * | 1967-04-10 | 1971-10-26 | Agfa Gevaert Ag | Optically sensitized light-sensitive silver halide material |
| US3617294A (en) * | 1968-09-09 | 1971-11-02 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3667960A (en) * | 1969-03-27 | 1972-06-06 | Fuji Photo Film Co Ltd | Spectrally supersensitized silver halide photographic emulsion |
-
1970
- 1970-07-16 JP JP45061738A patent/JPS4841205B1/ja active Pending
-
1971
- 1971-07-15 DE DE19712135413 patent/DE2135413A1/de active Pending
- 1971-07-15 US US00163100A patent/US3769024A/en not_active Expired - Lifetime
- 1971-07-16 GB GB3355071A patent/GB1318154A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2132866A (en) * | 1937-03-29 | 1938-10-11 | Eastman Kodak Co | Photographic emulsion |
| US3615634A (en) * | 1967-04-10 | 1971-10-26 | Agfa Gevaert Ag | Optically sensitized light-sensitive silver halide material |
| US3580724A (en) * | 1968-06-04 | 1971-05-25 | Konishiroku Photo Ind | Light-sensitive supersensitized silver halide color photographic emulsions |
| US3617294A (en) * | 1968-09-09 | 1971-11-02 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3667960A (en) * | 1969-03-27 | 1972-06-06 | Fuji Photo Film Co Ltd | Spectrally supersensitized silver halide photographic emulsion |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933510A (en) * | 1972-09-04 | 1976-01-20 | Fuji Photo Film Co., Ltd. | Spectrally sensitized silver halide photographic emulsion |
| US3953215A (en) * | 1973-07-16 | 1976-04-27 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsions |
| US3861920A (en) * | 1974-01-02 | 1975-01-21 | Polaroid Corp | Super-sensitizing dye combination in silver halide emulsions |
| USH899H (en) | 1986-03-25 | 1991-03-05 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic material feasible for high speed |
| US5077183A (en) * | 1987-12-24 | 1991-12-31 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material and a process for the preparation of a photographic silver halide emulsion |
| US4940657A (en) * | 1988-01-21 | 1990-07-10 | Mitsubishi Paper Mills Limited | Photographic spectral sensitizing dye |
| US5348849A (en) * | 1990-10-26 | 1994-09-20 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| CN102702769A (zh) * | 2012-06-20 | 2012-10-03 | 大连理工大学 | 一类绿光荧光菁染料、制备方法及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1318154A (en) | 1973-05-23 |
| JPS4841205B1 (enrdf_load_stackoverflow) | 1973-12-05 |
| DE2135413A1 (de) | 1972-01-20 |
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