US3656959A - Photographic silver halide emulsion - Google Patents
Photographic silver halide emulsion Download PDFInfo
- Publication number
- US3656959A US3656959A US755745A US3656959DA US3656959A US 3656959 A US3656959 A US 3656959A US 755745 A US755745 A US 755745A US 3656959D A US3656959D A US 3656959DA US 3656959 A US3656959 A US 3656959A
- Authority
- US
- United States
- Prior art keywords
- dye
- silver halide
- halide emulsion
- photographic silver
- ethyl
- 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
- 239000000839 emulsion Substances 0.000 title claims abstract description 47
- -1 silver halide Chemical class 0.000 title claims abstract description 46
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 38
- 239000004332 silver Substances 0.000 title claims abstract description 38
- 230000001235 sensitizing effect Effects 0.000 claims abstract description 28
- 239000000975 dye Substances 0.000 abstract description 80
- 150000001768 cations Chemical class 0.000 abstract description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 230000003595 spectral effect Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 125000004964 sulfoalkyl group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- PTBGZESVAJXTHX-UHFFFAOYSA-N 1h-benzimidazole;hydrate Chemical compound O.C1=CC=C2NC=NC2=C1 PTBGZESVAJXTHX-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- 150000001556 benzimidazoles Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- XXTISPYPIAPDGY-UHFFFAOYSA-N n,n-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1N(C=N)C1=CC=CC=C1 XXTISPYPIAPDGY-UHFFFAOYSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- OWIRVNDMYDSKIJ-UHFFFAOYSA-N 2,4-dichloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1Cl OWIRVNDMYDSKIJ-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- GYVLFYQMEWXHQF-UHFFFAOYSA-N 5,6-dichloro-1-ethylbenzimidazole Chemical compound ClC1=C(Cl)C=C2N(CC)C=NC2=C1 GYVLFYQMEWXHQF-UHFFFAOYSA-N 0.000 description 1
- NPPPLXJXZOCDHJ-UHFFFAOYSA-N 6-chloro-4-methylquinoline Chemical compound C1=C(Cl)C=C2C(C)=CC=NC2=C1 NPPPLXJXZOCDHJ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- XCFIVNQHHFZRNR-UHFFFAOYSA-N [Ag].Cl[IH]Br Chemical compound [Ag].Cl[IH]Br XCFIVNQHHFZRNR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom 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
- GTRLQRHWPXEBLF-UHFFFAOYSA-N benzyl carbamimidothioate Chemical class NC(=N)SCC1=CC=CC=C1 GTRLQRHWPXEBLF-UHFFFAOYSA-N 0.000 description 1
- WJAASTDRAAMYNK-UHFFFAOYSA-N benzyl carbamimidothioate;hydron;chloride Chemical compound Cl.NC(=N)SCC1=CC=CC=C1 WJAASTDRAAMYNK-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Definitions
- Z and Z are non-metallic groups necessary to complete a benzimidazole nucleus
- a and B are polymethylene groups or alkylpolymethylene groups.
- M is a cation.
- Preferred dyes are set out in the specification.
- the present invention relates generallyto a photographic silver halide emulsion containing a novel sensitizing dye, and more particularly to a photographic silver halide emulsion containing an unsymmetrical benzimidazolocarbocyanine dye in whichthe substituents of-the nitrogen atoms-in both heterocyclic rings are sulfoalkyl groups.
- a benzirnidazolocarbocyanine dye can provide a high spectral sensitivity to a silver halide emulsion, but the formation of fog is generally increased by the addition of such a dye.
- Symmetrical benzimidazolocarbocyanine dyes having sulfoalkyl groups at the nitrogen atoms in both heterocyclic rings are disclosed in the specifications of U. 5. Pat. No. 2,912,329 andBelgian patents 648,981 and 669,308. However, unsymmetrical benzimidazolocarbocyanine dyes having sulfoalkyl groups at the nitrogen atoms in both heterocyclic groups thereof have never been known.
- Z and Z each represent a non-metallic atomic group necessary to complete the benzimidazole nucleus;
- a and B each represents a member selected from the group consisting of a 'polymethylene group, and-an alkylpolymethylene group; and
- M represents a cation.
- For mostcommercial usage, about 5 mg. to I 50 mg. of dye perkilogramof emulsionwill-suffice.
- a photographic light-sensitive element containing the above-described emulsion shows'greatly improved results.
- Preferred dyes and'the various-moities operable are set-out in the descriptive portion of the specification.
- An object of this invention is to provide a photographic silver halide emulsion having a high sensitivity over the spectral sensitizing wavelength region by using a novel sensitizing dye which does not increase photographic fog caused by the sensitizing dye.
- Z and Z each represents non-metallic atoms necessary to complete the benzimidazole nucleus
- a and B which may be the same or different, each represents a polymethylene group, such as an ethylene group, a trimethylene group, and a tetramethylene group, or an alkylpolymethylene group such as a methyltrimethylene group
- M represents a hydrogen cation, a metallic ion necessary for forming a salt of sulfonic acid, such as, a potassium ion, a sodium ion, and the like, ora cation of an organic amine, such as a triethylammoniumion, a pyridinium ion, an-S-benzylthiuronium ion, and the like.
- the sensitizing dye used in the present invention is an unsymmetrical benzimidazolocarbocyanine dye having sulfoalkyl groups as substituents at the nitrogen atoms in both heterocyclic rings.
- benzimidazole nucleus formed by aforesaid atomic groups Z or 2' there are: l-ethylbenzimidazole, l-phenylbenzimidazole, l-methyl-S- chlorobenzimidazole, I--ethyI-5-chlorobenzimidazole, lmethyl-S,6-dichlorobenzimidazole, 1-ethyl-5,6- dichlorobenzimidazole, I-(B-hydroxyethyl)-5,6- dichlorobenzimidazole, I-(y-acetoxypropyl)-5,6-
- the sensitizing dye of the present invention is an unsymmetrical benzimidazolocarbocyanine dye which has sulfoalkyl groups at the nitrogen atoms in both heterocyclic rings thereof in combination with properly selected substituents in both heterocyclic rings.
- the sensitivity of .the desired spectral wavelength region of a photographic silver halide emulsion can'be increased by adding the sensitizing dye described thereto without increasing the formation of fog to any significant extent.
- the sensitizing dye used in this invention also has great merit that the alkyl groups of the nitrogen atoms in both heterocyclic rings of the dye and the alkylene .chains of the sulfoalkyl groups may be selected from a large class.
- novel sensitizing dye represented by general formula -(I) may be prepared by reacting-an anilinovinyl intermediate compound having a sulfoalkyl ,group as a substituent of the (wherein Z and A are defined in connection with-general formula (I) with acetic anhydride in nitrobenzene, to provide an acetoanilidovinyl intermediate product, and condensing the intermediate product in the presence of an organic base, such as triethylamine, with an intermediate represented by general formula (III):
- ether was added to the reaction product to precipitate the dye, which was recovered by filtration, washed with ether and then treated with an aqueous solution of potassium acetate to convert the dye into the potassium salt of the dye.
- the potassium salt was recrystallized from a mixed solvent of methanol and isopropanol, 0.7 g. of the crystal of dye 6, having a melting point greater than 300 C., was obtained.
- the spectral absorption maximum of the dye in methanol was 512 m. .r.
- the novel sensitizing dye used in the present invention can spectrally sensitize silver halide emulsions and in particular, the dye is very effective for enlarging the spectrally sensitive region of a gelatino silver halide emulsion.
- the sensitizing dye can also sufficiently sensitize photographic silver halide emulsions containing hydrophilic colloids other than gelatin, such as, agar agar, collodion, water-soluble cellulose derivatives, polyvinyl alcohol, and other natural or synthetic hydrophilic resins.
- hydrophilic colloids other than gelatin such as, agar agar, collodion, water-soluble cellulose derivatives, polyvinyl alcohol, and other natural or synthetic hydrophilic resins.
- such silver salts as silver chloride, silver bromide, silver iodobromide, silver chlorobromide, and silver chloro-iodobromide may be employed.
- one or more of the aforesaid novel sensitizing dyes may be incorporated in a photographic silver halide emulsion by any conventional method.
- the dye is usually added to a photographic emulsion as a solution thereof in a solvent such as methanol or ethanol.
- the amount of the sensitizing dye to be incorporated in the photographic emulsion may be varied within a very wide range, but for most commercial uses, it has been found that from 5 mg. to mg. per kilogram of emulsion, according to desired end result, is suitable.
- the photographic silver halide emulsion of this invention may further be subjected to super sensitization and hyper sensitization.
- the usual additives such as a chemical sensitizer, a stabilizer, an antibronzing agent, a hardening agent, a surface active agent, an antifoggant, a plasticizer, a developing accelerator, a color coupler, and a fluorescent whitening agent. Any conventional methods may be used for the addition.
- the photographic silver halide emulsion of this invention may be applied to a support such as a glass plate, a cellulose derivative film, a synthetic resin film, or a baryta paper by any conventional methods to provide photographic light-sensitive elements.
- EXAMPLE A photographic silver halide emulsion was prepared by adding the sensitizing dye of this invention mentioned above to a silver iodobromide emulsion (Agl AgBr 7 mol 93 mol). The photographic emulsion was applied to a triacetyl cellulose film and dried. The photographic light sensitive film was exposed to a lamp (color temperature 2,660 K.) and after development, the spectral sensitizing characteristics were measured by means of a diffraction grating spectrometer.
- composition of the developer used above was as follows:
- the sensitization maximums when various sensitizing dyes of this invention were used are shown in Table 1, and the fog densities of the photographic light-sensitive elements prepared by using the photographic silver halide emulsions of this invention are shown in Table 2 together with those of comparative light-sensitive elements using other photographic silver halide emulsions containing conventional control sensitizing dyes shown below.
- said dye is (A).
- a photographic light-sensitive element which comprises a layer of photographic silver halide emulsion claimed in claim 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5543967 | 1967-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3656959A true US3656959A (en) | 1972-04-18 |
Family
ID=12998610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US755745A Expired - Lifetime US3656959A (en) | 1967-08-29 | 1968-08-27 | Photographic silver halide emulsion |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3656959A (enrdf_load_stackoverflow) |
| BE (1) | BE719803A (enrdf_load_stackoverflow) |
| DE (1) | DE1797199A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1577843A (enrdf_load_stackoverflow) |
| GB (1) | GB1242588A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| US5354646A (en) * | 1986-03-26 | 1994-10-11 | Konishiroku Photo Industry Co., Ltd. | Method capable of rapidly processing a silver halide color photographic light-sensitive material |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59188641A (ja) | 1983-04-11 | 1984-10-26 | Fuji Photo Film Co Ltd | ハロゲン化銀写真乳剤 |
| JPS61245151A (ja) | 1985-04-23 | 1986-10-31 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPS61251852A (ja) | 1985-04-30 | 1986-11-08 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料の処理方法 |
| JPS61250645A (ja) | 1985-04-30 | 1986-11-07 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPS61250643A (ja) | 1985-04-30 | 1986-11-07 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| AU591540B2 (en) | 1985-12-28 | 1989-12-07 | Konishiroku Photo Industry Co., Ltd. | Method of processing light-sensitive silver halide color photographic material |
| DE69131785T2 (de) | 1990-08-20 | 2000-05-11 | Fuji Photo Film Co., Ltd. | Datenbehaltendes photographisches Filmerzeugnis und Verfahren zur Herstellung eines Farbbildes |
| US5476760A (en) | 1994-10-26 | 1995-12-19 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2912329A (en) * | 1957-08-23 | 1959-11-10 | Eastman Kodak Co | Green sensitization for photographic emulsions containing coupler dispersions |
-
1968
- 1968-08-22 BE BE719803D patent/BE719803A/xx unknown
- 1968-08-27 US US755745A patent/US3656959A/en not_active Expired - Lifetime
- 1968-08-29 DE DE19681797199 patent/DE1797199A1/de active Pending
- 1968-08-29 FR FR1577843D patent/FR1577843A/fr not_active Expired
- 1968-08-29 GB GB41372/68A patent/GB1242588A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2912329A (en) * | 1957-08-23 | 1959-11-10 | Eastman Kodak Co | Green sensitization for photographic emulsions containing coupler dispersions |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| US5354646A (en) * | 1986-03-26 | 1994-10-11 | Konishiroku Photo Industry Co., Ltd. | Method capable of rapidly processing a silver halide color photographic light-sensitive material |
| US5582957A (en) * | 1995-03-28 | 1996-12-10 | Eastman Kodak Company | Resuspension optimization for photographic nanosuspensions |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1577843A (enrdf_load_stackoverflow) | 1969-08-08 |
| BE719803A (enrdf_load_stackoverflow) | 1969-02-03 |
| DE1797199A1 (de) | 1970-12-10 |
| GB1242588A (en) | 1971-08-11 |
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