US3694217A - Silver halide photographic emulsion - Google Patents
Silver halide photographic emulsion Download PDFInfo
- Publication number
- US3694217A US3694217A US865545A US3694217DA US3694217A US 3694217 A US3694217 A US 3694217A US 865545 A US865545 A US 865545A US 3694217D A US3694217D A US 3694217DA US 3694217 A US3694217 A US 3694217A
- Authority
- US
- United States
- Prior art keywords
- group
- silver halide
- agbr
- sensitizing
- 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
Links
- 239000000839 emulsion Substances 0.000 title abstract description 48
- -1 Silver halide Chemical class 0.000 title abstract description 30
- 229910052709 silver Inorganic materials 0.000 title abstract description 27
- 239000004332 silver Substances 0.000 title abstract description 27
- 230000001235 sensitizing effect Effects 0.000 abstract description 52
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001450 anions Chemical class 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 229910052711 selenium Inorganic materials 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 239000011593 sulfur Substances 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 54
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 29
- 230000035945 sensitivity Effects 0.000 description 26
- 206010070834 Sensitisation Diseases 0.000 description 21
- 230000008313 sensitization Effects 0.000 description 20
- 230000003595 spectral effect Effects 0.000 description 20
- 238000001228 spectrum Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010724 Wisteria floribunda Nutrition 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WPNJAUFVNXKLIM-UHFFFAOYSA-N Moxonidine Chemical compound COC1=NC(C)=NC(Cl)=C1NC1=NCCN1 WPNJAUFVNXKLIM-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000000217 alkyl 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
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 239000000203 mixture Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012260 resinous material Substances 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
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/134—Brightener containing
Definitions
- This invention relates to a spectrally sensitized silver halide photographic emulsion and, more particularly, to a silver halide photographic emulsion having a maximum spectral sensitization within the range of from about 620 my. to 645 mg and a high sensitivity to red light.
- the sensitizing effect in a. longer wave length region of a sensitizing dye having its maximum spectral sensitization in a longer wave length region is greatly affected by the other sensitizing dye having its spectral sensitivity in a shorter wave length region and, in general, the sensitization efiect (attributable to the aggregation of sensitizing dyes on particles of silver halide) in a longer wave length region is lowered.
- the principal object of the present invention is to provide a silver halide photographic emulsion containing a novel sensitizing dye which will aiford a high spectral sensitivity in a spectral sensitization wave length region of about 620 to 645 mp. without any decrease in either the total sensitivity and in the red sensitivity, even when used in combination with an ortho sensitizer, and further, which will not retain any stain in the sensitive material after development.
- FIGS. l-4 show spectral sensitization spectra obtained by employing a dye of the present invention alone, in combination with known dyes, and by employing a conventional dye alone and in combination with other known dyes, respectively.
- the special feature of the chemical structure of the sensitizing coloring matter used in the present invention consists of the substituents R and R. It has been found that the spectral sensitizing property of, especially, mesomethylthiacarbocyanines, mesomethylselenathiacarbocyanines and mesomethylselenacarbocyanines is affected to a great extent by the substituents R and R.
- mesomethylcarbocyanine dyes are used in combination with a known ortho sensitizing dye, such as thia-2'-cyanine or 2,2'-cyanine, its sensitizing property in a red region corresponding to the maximum spectral sensitization (approximately 620 to 645 m due to the aggregation of the mesomethylcarbocyanine dye on the silver halide particles is adversely affected, and, consequently, the red sensitivity of the emulsion is lowered to a great extent, so that the use of such mesomethylcarbocyanines is disadvantageous for the object of the present invention.
- a known ortho sensitizing dye such as thia-2'-cyanine or 2,2'-cyanine
- the sensitizing dye of the present invention is able to spectrally sensitize silver halide photographic emulsions.
- emulsion used in the present invention may be an emulsion which contains a mixed silver halide, such as silver iodobromide or silver chlorobromoiodide.
- the photoemulsion which is sensitized in accordance with the present invention may be prepared by incorporating one or more sensitizing dyes in a photographic emulsion in an ordinary manner.
- the dye is usually added to the emulsion while in solution in a suitable solvent, such as methanol or ethanol.
- the amount of the sensitizing dye to be incorporated in the emulsion may vary in a wide range of from 5 to 200 mg. per kg. of emulsion, depending on the required effect.
- the photographic emulsion used in accordance with the present invention may be, in addition, super-sensitized and hyper-sensitized according to conventional methods.
- the photographic emulsion in accordance with the present invention may be applied in the usual manner to a suitable support, such as, e.g., sheet glass, a film of cellulose derivative, a film of synthetic resin or baryta paper.
- a suitable support such as, e.g., sheet glass, a film of cellulose derivative, a film of synthetic resin or baryta paper.
- Fuji #7 filter made by Fuji Photo Film Co., Ltd., transmitting light having a wave length longer than 580 mg
- the developing solution used was of the formulation as indicated in Table 2.
- Table 3 is shown the degrees of color sensitization and maxima of sensitization obtained by separate addition of the sensitizing dyes as indicated in Table 1.
- Table 4 is shown the degrees of spectral sensitization and maxima of sensitization obtained by the separate addition of the sensitizing dyes indicated above as sensitizing dyes for comparison.
- Table 5 is shown the degrees of spectral sensitization and maxima of sensitization obtained by various combinations of sensitizing dyes selected from those listed in Table l and those as indicated above for comparison with a known green-sensitive sensitizing dye.
- the red sensitivities were indicated by terms of relative sensitivity, assuming that the red sensitivity of sensitizing coloring matter A was 100.
- sensitizing dye F 0. 015 AgBr/I 625 80
- the red sensitivities were indicated in terms of relative sensitivity, assuming that the red sensitivity of an emulsion having incorporated therein, by itself, sensitizing dye F was 100.
- FIG. 1 indicates a spectral sensitization spectrum obtained by using great extent when used in combination with green-sensitization spectrum obtained by using sensitizing dye 3 in combination with known green-sensitive coloring matter H and I;
- FIG. 3 indicates aspectral sensitization spectrum obtained by using sensitizing dye E alone;
- FIG. 4 indicates a spectral sensitization spectrum obtained by using sensitizing dye F in combination with the known green-sensitive sensitizing dyes H and I.
- sensitizing dye E was used for compan'sion purposes, its maximum sensitization in the red region (J-band) falls off to a great extent when used in combination witht green-sensitive sensitizing dye H and this causes a remarkable depression of the red sensitivity, while, when employing sensitizing dye 3 of the present invention, the phenomenon that will cause such a depression of red sensitivity does not occur even if it is used in combination with the green-sensitive sensitizing dyes H and I.
- the known green-sensitive sensitizing dyes used in combination with the sensitizing dye of the present in- The red sensitivities were indicated in terms of relative 75 vention are those having the following structures.
- Z and Z are individually selected from the group consisting of a sulfur and a selenium atom
- R is selected from the group consisting of an ethyl group, an n-propyl group, an n-butyl group and an allyl group
- R' is selected from the group consisting of an 'y-sulfopropyl group, a 'ysulfobutyl group, a a-sulfobutyl group, a B-carboxybutyl group and a w-carboxypentyl group
- X represents an anion
- n is or 1, n being 0 when the dye is an intramolecular salt.
- the silver halide photographic emulsion as in claim group consisting of p 1 Br CzHs l? CH N N Br- (5 2H5 2 5 8.
Landscapes
- 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)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6570468 | 1968-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3694217A true US3694217A (en) | 1972-09-26 |
Family
ID=13294656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US865545A Expired - Lifetime US3694217A (en) | 1968-09-12 | 1969-09-12 | Silver halide photographic emulsion |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3694217A (enrdf_load_stackoverflow) |
| DE (1) | DE1946307C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2019427B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1280016A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3446962A1 (de) * | 1983-12-22 | 1985-07-04 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photographisches silberhalogenid-druckpapier und verwendung des papiers im schwarz-weiss-entwicklungsverfahren |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| US4690883A (en) * | 1984-12-14 | 1987-09-01 | Fuji Photo Film Co., Ltd. | Image forming process |
| JPH01302351A (ja) * | 1988-05-31 | 1989-12-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| 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 |
| US5456999A (en) * | 1991-11-29 | 1995-10-10 | Agfa-Gevaert, N.V. | Infrared sensitive silver halide photographic 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB498290A (en) * | 1937-03-25 | 1938-12-28 | Eastman Kodak Co | Improvements in sensitised photographic emulsions |
| DE917330C (de) * | 1940-10-22 | 1955-01-10 | Agfa Ag Fuer Photofabrikation | Verfahren zur Herstellung von am mittelstaendigen Kohlenstoffatom der Methinkette substituierten, symmetrischen und unsymmetrischen Carbocyaninen |
| BE484580A (enrdf_load_stackoverflow) * | 1947-08-29 | |||
| DE929080C (de) * | 1951-10-23 | 1955-08-16 | Agfa Ag Fuer Photofabrikation | Verfahren zur Herstellung von Betain-Cyanin-Farbstoffen und von Betain-Styryl-Farbstoffen |
| BE548605A (enrdf_load_stackoverflow) * | 1956-03-07 | |||
| GB841119A (en) * | 1957-09-02 | 1960-07-13 | Ici Ltd | New photographic sensitisers |
| US2917516A (en) * | 1957-11-25 | 1959-12-15 | Eastman Kodak Co | Method of making thiazole or oxazole quaternary salts |
| DE1113873B (de) * | 1959-01-17 | 1961-09-14 | Wolfen Filmfab Veb | Verfahren zur Sensibilisierung von Halogensilberemulsionen |
| GB1027053A (en) * | 1963-08-26 | 1966-04-20 | Ilford Ltd | Photographic light-sensitive materials |
-
1969
- 1969-09-11 FR FR696931013A patent/FR2019427B1/fr not_active Expired
- 1969-09-12 US US865545A patent/US3694217A/en not_active Expired - Lifetime
- 1969-09-12 DE DE1946307A patent/DE1946307C2/de not_active Expired
- 1969-09-12 GB GB45170/69A patent/GB1280016A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3446962A1 (de) * | 1983-12-22 | 1985-07-04 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photographisches silberhalogenid-druckpapier und verwendung des papiers im schwarz-weiss-entwicklungsverfahren |
| US4657846A (en) * | 1983-12-22 | 1987-04-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic printing paper |
| US4690883A (en) * | 1984-12-14 | 1987-09-01 | Fuji Photo Film Co., Ltd. | Image forming process |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive 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 |
| JPH01302351A (ja) * | 1988-05-31 | 1989-12-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| US5456999A (en) * | 1991-11-29 | 1995-10-10 | Agfa-Gevaert, N.V. | Infrared sensitive silver halide photographic 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1280016A (en) | 1972-07-05 |
| FR2019427B1 (enrdf_load_stackoverflow) | 1973-05-11 |
| FR2019427A1 (enrdf_load_stackoverflow) | 1970-07-03 |
| DE1946307C2 (de) | 1983-10-20 |
| DE1946307A1 (de) | 1970-05-14 |
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