US3666480A - Spectrally sensitized silver halide photographic emulsion - Google Patents
Spectrally sensitized silver halide photographic emulsion Download PDFInfo
- Publication number
- US3666480A US3666480A US85229A US3666480DA US3666480A US 3666480 A US3666480 A US 3666480A US 85229 A US85229 A US 85229A US 3666480D A US3666480D A US 3666480DA US 3666480 A US3666480 A US 3666480A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- formula
- halide photographic
- group
- 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 abstract description 31
- 229910052709 silver Inorganic materials 0.000 title abstract description 21
- 239000004332 silver Substances 0.000 title abstract description 21
- -1 silver halide Chemical class 0.000 title abstract description 21
- 230000001235 sensitizing effect Effects 0.000 abstract description 21
- 239000002253 acid Substances 0.000 abstract description 5
- 150000001450 anions Chemical class 0.000 abstract description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 150000001556 benzimidazoles Chemical class 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 abstract 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 41
- 230000035945 sensitivity Effects 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 235000019441 ethanol Nutrition 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
- 239000000203 mixture Substances 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 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
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AGJZCWVTGOVGBS-UHFFFAOYSA-N 1,1'-diethyl-2,2'-cyanine Chemical compound C1=CC2=CC=CC=C2N(CC)\C1=C\C1=CC=C(C=CC=C2)C2=[N+]1CC AGJZCWVTGOVGBS-UHFFFAOYSA-N 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical group C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- 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
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000004453 alkoxycarbonyl 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
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle 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
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- R R R and R each represent alkyl groups, at least one of said R and R being an alkyl group having a sulfo group; Z and Z represent the non-metallic atomic groups necessary to complete a benzimidazole nucleus; X represents an acid anion and p represents an integer of 1 or 2, p being 1 when said dye forms an intermolecular salt; and at least one sensitizing dye represented by the following second Formula:
- This invention relates to a spectrally sensitized silver halide photographic emulsion, in particular, one which is supersensitized in the green region.
- spectral sensitization is a very important technique employed in the making of a silver halide photographic emulsion, in particular, a color photosensitive material.
- the spectral sensitivity depends on the chemical structure and property of the sensitizing dye used and the property of the silver halide used, for example, halogen composition, crystal habit, chemical ripening, pAg and pH.
- the spectral sensitivity also depends on the various additives to the emulsion, many of which decrease the spectral sensitivity. In the case of an emulsion used in the making of an incorporated type color photographic material, the sensitivity is decreased by the introduction of a coupler. This efiect 3,666,480 Patented May 30, 1972 is a large obstacle in the making of photographic material.
- This object can be accomplished by the use of a supersensitized silver halide photographic emulsion wherein at least one sensitizing dye represented by the following General Formula I and at least one sensitizing dye represented by the following General Formula II is added to the emulsion:
- R and R being an alkyl group having a sulfo group
- Z and Z represent the non-metallic atoms necessary to complete a benzimidazole nucleus
- X represents an acid anion group
- p represents an integer of 1 or 2, p being 1 when said dye forms an intermolecular salt.
- the spectrally sensitized silver halide photographic emulsion can advantageously be used in combination with the oxacarbocyanine dye disclosed in Japanese patent publication No. 4936/68 or with the hemicyanine dye disclosed in Belgian Patent No. 724,467.
- R R R R and R the alkyl groups may be, for example, methyl, ethyl propyl, acetoxypropyl, hydroxyethyl, allyl, benzyl, 'y-sulfopropyl, 'y-sulfobutyl, 5-sulfo butyl, 2-(3-su1fopropoxy) ethyl, 2-[2-(3-sulfopropoxy) ethoxy] ethyl or Z-hydroxy-l-sulfopropyl groups.
- Examples of X and X are chlorine, bromine, iodine, perchlorate, thiocyanate, p-toluene sulfonate, benzenesulfonate, methyl sulfonate and ethyl sulfate ions.
- One feature of the invention lies in the substituent of the l -forming nucleus in Formula II.
- the substituent f the invention is useful for raising the sensitivity in the 515-530 my range in connection with the property of the dye I aggregate and to obtain a suitable spectral sensi tivity.
- the dye of Formula I is the well-known benzimidazolocarbocyanine.
- the nucleus substituent of said benzimidazole includes those mentioned in Japanese patent publication Nos. 4936/68, 2884/68, 2530/69 and 16589/69.
- the compounds of Formula II can also readily be synthesized by known methods such as those disclosed in United States Patent No. 2,503,776.
- a typical method for the synthesis of compound HA is as follows: 850 mg. of 6 methyl-Z-ethylmercapto-l-ethylquinolinium ethyl sulfate and 800 mg. of anhydro-S-carbomethoxy-Z-methyl- 3 (y-sulfopropyl)-benzothiazolium hydroxide are dissolved in ml. of ethyl alcohol, to which is added 3.5 ml. of triethylamine, and heated for 4 hours with refluxing.
- the dye used in this invention may be added to the emulsion in the form of a solution in water or in a watersoluble organic solvent such as methanol, ethanol, pyridine, acetone or Cellosolve.
- the sensitizing dyes represented by Formulae I and II may be added as individual solutions or as a mixed solution. Dissolving may be effected by ultrasonic wave agitation.
- the amount of each dye may be varied with the emulsion employed. Ordinarily, the amount of both dyes is preferably from 1X10- mole to 1X10 mole per 1 mole of silver halide.
- the weight proportion of the dye of Formula I to the dye of Formula II varies from :1 to 1:2, and preferably from 4:1 to 2: 1. This proportion may also be varied depending on the use of other additives in the emulsion.
- the silver halide emulsions which may be used are, for example, silver iodobromide, silver bromide and silver chlorobromide.
- a silver iodobromide emulsion is advantageous to use, because its particle size is not particularly restricted.
- Gelatino-silver halide emulsions are mainly used, but binders other than gelatin may, of course, be used, for example, polyvinyl alcohol, alginate polymers, polyvinyl imidazole, polyvinylpyrrolidone and mixtures thereof with gelatin.
- the silver halide emulsion of the present invention is coated onto a suitable support, depending on its use, for example, baryta paper, cellulose triacetate film, polyethylene terephthalate film, plastic films resin-coated paper or synthetic paper.
- the sample was cut into strips and subjected to light wedge exposure through a yellow filter of No. K-12 (trademartk) using a sensitometer having a light source color temperature of 5400 K. It was then developed at 20 C. for 12 minutes with the following developer composition:
- the sample was passed through a first fixing solution, a bleaching solution and a second fixing solution and washed with water to obtain a magenta image.
- the green filter density was measured with an S-type (trademark) densitometer manufactured by Fuji Photo Film Co., Ltd.
- S-type (trademark) densitometer manufactured by Fuji Photo Film Co., Ltd.
- R R R and R each represent alkyl groups, at least one of said R and R being an alkyl group having a sulfo group Z and Z represent the non-metallic atomic groups necessary to complete a benzimidazole nucleons;
- X represents an acid anion and p represents an integer of 1 or 2, p being 1 when said dye forms an intermolecular salt; and at least one sensitizing dye represented by the following second formula:
- R represent alkyl groups, at least one of said R wherein R and 2;, have the same meaning as in claim 1, wherein R represents a methyl or ethyl group, and wherein n represents 2, 3 or 4.
- iomcrnomcmnsoi iomcrnomcmnsoi and at least one sensitizing dye represented by the following formula:
- R R Z and n have the same meaning as in claim 3.
- R R Z and n have the same meaning as in claim 3.
- a photographic light-sensitive element comprising a l (CHaCHgO) ;(GH S OsHN (C2116):
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44086580A JPS4838407B1 (enrdf_load_stackoverflow) | 1969-10-29 | 1969-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3666480A true US3666480A (en) | 1972-05-30 |
Family
ID=13890928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US85229A Expired - Lifetime US3666480A (en) | 1969-10-29 | 1970-10-29 | Spectrally sensitized silver halide photographic emulsion |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3666480A (enrdf_load_stackoverflow) |
| JP (1) | JPS4838407B1 (enrdf_load_stackoverflow) |
| BE (1) | BE758115A (enrdf_load_stackoverflow) |
| DE (1) | DE2053187C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2066635A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1328274A (enrdf_load_stackoverflow) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3765899A (en) * | 1969-03-14 | 1973-10-16 | Konishiroku Photo Ind | Light-sensitive super-sensitized silver halide photographic emulsion |
| US3849147A (en) * | 1969-06-25 | 1974-11-19 | Fuji Photo Film Co Ltd | Silver halide supersensitized photographic emulsion |
| US3856532A (en) * | 1972-04-26 | 1974-12-24 | Ilford Ltd | Photographic silver halide emulsion containing a supersensitising combination |
| US3873324A (en) * | 1973-02-28 | 1975-03-25 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| US3969116A (en) * | 1971-01-19 | 1976-07-13 | Fuji Photo Film Co., Ltd. | Silver halide photographic sensitive element for flash exposure |
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US4710631A (en) * | 1984-08-28 | 1987-12-01 | Fuji Photo Film Co., Ltd. | Temperature compensation for a semiconductor light source used for exposure of light sensitive material |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP1624337A2 (en) | 2004-08-02 | 2006-02-08 | Fuji Photo Film Co., Ltd. | Silver halide holographic sensitive material and system for taking holographic images by using the same |
| EP1691237A2 (en) | 2005-02-15 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Holographic recording material and holographic recording method |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
| EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5981221A (ja) * | 1982-10-29 | 1984-05-10 | Nissan Motor Co Ltd | プラスチツク製燃料タンク |
| US4725529A (en) | 1985-04-30 | 1988-02-16 | Konishiroku Photo Industry Co., Ltd. | Developing inhibitor arrangment in light-sensitive silver halide color photographic materials |
| AU590563B2 (en) | 1985-05-16 | 1989-11-09 | Konishiroku Photo Industry Co., Ltd. | Method for color-developing a silver halide color photographic light-sensitive material |
| JPH01170024U (enrdf_load_stackoverflow) * | 1988-05-11 | 1989-11-30 |
-
0
- BE BE758115D patent/BE758115A/xx unknown
-
1969
- 1969-10-29 JP JP44086580A patent/JPS4838407B1/ja active Pending
-
1970
- 1970-10-28 FR FR7038819A patent/FR2066635A5/fr not_active Expired
- 1970-10-29 DE DE2053187A patent/DE2053187C3/de not_active Expired
- 1970-10-29 US US85229A patent/US3666480A/en not_active Expired - Lifetime
- 1970-10-29 GB GB5159670A patent/GB1328274A/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3765899A (en) * | 1969-03-14 | 1973-10-16 | Konishiroku Photo Ind | Light-sensitive super-sensitized silver halide photographic emulsion |
| US3849147A (en) * | 1969-06-25 | 1974-11-19 | Fuji Photo Film Co Ltd | Silver halide supersensitized photographic emulsion |
| US3969116A (en) * | 1971-01-19 | 1976-07-13 | Fuji Photo Film Co., Ltd. | Silver halide photographic sensitive element for flash exposure |
| US3856532A (en) * | 1972-04-26 | 1974-12-24 | Ilford Ltd | Photographic silver halide emulsion containing a supersensitising combination |
| US3873324A (en) * | 1973-02-28 | 1975-03-25 | Fuji Photo Film Co Ltd | Spectrally sensitized silver halide photographic emulsion |
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US4710631A (en) * | 1984-08-28 | 1987-12-01 | Fuji Photo Film Co., Ltd. | Temperature compensation for a semiconductor light source used for exposure of light sensitive material |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| US5418124A (en) * | 1992-03-19 | 1995-05-23 | Fuji Photo Film Co. Ltd. | Silver halide photographic emulsion and a photographic light-sensitive material |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
| EP1624337A2 (en) | 2004-08-02 | 2006-02-08 | Fuji Photo Film Co., Ltd. | Silver halide holographic sensitive material and system for taking holographic images by using the same |
| EP1691237A2 (en) | 2005-02-15 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Holographic recording material and holographic recording method |
| 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 |
|---|---|
| FR2066635A5 (enrdf_load_stackoverflow) | 1971-08-06 |
| BE758115A (fr) | 1971-04-01 |
| GB1328274A (en) | 1973-08-30 |
| JPS4838407B1 (enrdf_load_stackoverflow) | 1973-11-17 |
| DE2053187B2 (de) | 1973-10-18 |
| DE2053187C3 (de) | 1974-05-16 |
| DE2053187A1 (de) | 1971-05-13 |
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