US3677765A - Silver halide supersensitized photographic emulsion - Google Patents
Silver halide supersensitized photographic emulsion Download PDFInfo
- Publication number
- US3677765A US3677765A US114338A US3677765DA US3677765A US 3677765 A US3677765 A US 3677765A US 114338 A US114338 A US 114338A US 3677765D A US3677765D A US 3677765DA US 3677765 A US3677765 A US 3677765A
- Authority
- US
- United States
- Prior art keywords
- agbr
- silver halide
- alkyl group
- group
- nucleus
- 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 35
- -1 Silver halide Chemical class 0.000 title abstract description 21
- 229910052709 silver Inorganic materials 0.000 title abstract description 19
- 239000004332 silver Substances 0.000 title abstract description 19
- 230000001235 sensitizing effect Effects 0.000 abstract description 45
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical class C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 abstract description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001450 anions Chemical class 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 55
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 53
- 230000035945 sensitivity Effects 0.000 description 19
- 206010070834 Sensitisation Diseases 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000008313 sensitization Effects 0.000 description 12
- 230000003595 spectral effect Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 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 5
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 5
- 235000010724 Wisteria floribunda Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 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 2
- 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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 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 1
- 229920001817 Agar Polymers 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
- 229910021612 Silver iodide Inorganic materials 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
- 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
- 125000003118 aryl group Chemical group 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
- 229910021538 borax Inorganic materials 0.000 description 1
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- DHHNSJJTDFVVSG-UHFFFAOYSA-L disodium;benzene-1,4-diol;sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O.OC1=CC=C(O)C=C1 DHHNSJJTDFVVSG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000006870 function Effects 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
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
- G03C1/28—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
-
- 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- 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
- R and R each represents a lower alkyl group or a substituted lower alkyl group
- Z and Z each represents an atomic group necessary to complete a benzothiazole nucleus, a benzoselenazole nucleus or a naphthothiazole nucleus
- X represents an anion
- R represents a lower alkyl group and R R Z 2,, X and In each has the same meaning as R R Z Z X and n respectively.
- the present invention relates to a spectrally sensitized silver halide light-sensitive photographic emulsion and especially to a silver halide light-sensitive photographic emulsion in which at least two sensitizing dyes are used in combination, by which a Wavelength region spectrally sensitized by each sensitizing dye is super-sensitized and a high red-sensitivity is obtained.
- the spectral sensitizing fllHCilOll obtained by the use of a sensitizing dye having a limited chemical structure may be additionally strengthened by using it together with another sensitizing dye or organic compound having a certain limited chemical structure. This phenomenon is known as a supersensitization function.
- An object of the present invention is to provide a silver halide photographic light-sensitive emulsion having a high red-sensitivity in a spectral sensitized wavelength range of 620-690 nm. by using two different kinds of sensitizing dyes in combination.
- This wavelength range is a spectral wavelength range used widely in black and white sensitive materials or in color photographic redsensitive layers.
- R and R each represents a lower alkyl group (for example, methyl or ethyl, etc.) or a substituted alkyl group commonly used in sensitizing dyes (for example, a 'y-sulfopropyl group, a 'y-sulfobutyl group, a li-sulfobutyl group, a B-hydroxyethyl group, a fi-carboxy propyl group, a e-carboxybutyl group or an allyl group, etc.); 2, and 2;, each represents an atomic group necessary to complete a benzothiazole nucleus, a benzoselenazole nucleus or a naphthothiazole nucleus, wherein the nucleus may be substituted with, for example, a halogen atom (for example, chlorine or bromine, etc.), a lower alkyl group, a hydroxyl group, an alkoxyl group (for example, methoxy or
- cyanine dyes for example, a chlorine, bromine, iodine, p-toluenesulfonic acid or an ethylsulfonic acid ion, etc.
- n 0 or 1, n being 0 when an intra-molecular salt is formed
- R represents a lower alkyl group (for example methyl or ethyl, etc.)
- R and R each represents a lower alkyl group (for example, methyl or ethyl, etc.) or a substituted alkyl group (for example, 'y-sulfopropyl, 'ysulfobutyl, B-sulfobutyl, B-hydroxypropyl, fl-carboxyethyl or allyl, etc.)
- Z each represents a group of atoms necessary to form a benzothiazole nucleus, a benzoselenazole nucleus or a naphthothiazole nucleus, wherein the nucleus may be substituted with, for example, a halogen atom (for example, chlorine or bromine, etc.), a lower alkyl group (for example, methyl, ethyl, propyl, etc.) an alkoxy group (for example, methoxy or e
- cyanine dyes for example, a chlorine, bromine, iodine, p-toluenesulfonic acid or ethylsulfonic acid ion, etc.
- m represents or 1, m being 0 when an intra-molecular salt is formed.
- sensitizing dye (I) A characteristic of the sensitizing dye represented by Formula I (hereinafter termed sensitizing dye (I) is that the hydrogen atom at the B-position of the methine chain of the cyanine dye containing a benzothiazole nucleus, a benzoselenazole nucleus or a naphthothiazole nucleus is replaced with a phenylethyl group.
- Such cyanine dyes easily form an optical (color) sensitization range which has a comparatively easy inclination at the long wavelength side of the maximum sensitization part.
- sensitizing dye (l1) easily form an optical (color) sensitization range which has a comparatively steep inclination at the long wavelength side of the maximum sensitization part.
- a high red-sensitivity can be obtained by using a combination of sensitizing dyes (I) and (II) as compared with the cases of using each sensitizing dye by itself. Further, it is possible to use the dyes together with an optical sensitizer in order to increase the green-sensitivity (a pseudocyanine dye, etc.) or othefl optical sensitizers having other spectral sensitization ranges.
- sensitizing dyes which may be used in the present invention.
- sensitizing dyes shown below are merely given as examples, applicants having no intention of being limited thereto.
- sensitizing dyes represented by Formulae I and II used in the present invention can be produced by any known method.
- the sensitizing dyes represented by Formula I are prepared by reacting a compound represented by Formula III:
- R X and n have the same meaning as in Formula I, and R represents an alkyl group (for example, methyl or ethyl, etc.), with a compound represented by Formula IV):
- the spectral sensitization method of the present invention is elfective for spectrally sensitizing gelatino silver halide protographic emulsions. Further, it is possible to sufliciently sensitize emulsions containing a hydrophilic colloid, excepting gelatin, such as agar-agar collodion, water-soluble cellulose derivatives, polyvinyl alcohol and other synthetic or natural hydrophilic resins by this method.
- mixed silver halide emulsions such as of silver iodo bromide and silver chloroiodo bromide are suitable.
- sensitizing dyes (I) and (II) may be admixed with the photographic emulsion by any common method.
- coloring material is usually added as a solution in a suitable solvent such as methanol or ethanol to the emulsion.
- the amount of sensitizing dyes (I) or (H) is preferably within the range of from mole to 10- mole of dye per mole of silver halide.
- the molar ratio of sensitizing dye (I) to dye (II) used in the emulsion can vary over a wide range of 9:1-lz9 according to the desired eifect.
- the photographic emulsion of the present invention can be subjected to hypersensitization and supersensitization by any well known method.
- additives commonly used such as sensitizers, stabilizers, color controlling agents, hardeners, surface active agents, antifogging agents, plasticizers, development accelerators, color 8 formers or whitening fluorescent agents, etc., can be added to the emulsion by usual methods.
- the photographic emulsion of the present invention can be applied to a suitable support such as glass, films of cellulose derivatives, synthetic resin films and baryta paper by any common method.
- silver halide photographic emulsions which contain a combination of sensitizing dyes (I) and (II) were prepared.
- the resulting films were exposed to a 64-lux daylight lamp (corresponding to 5400 K.) as the light source through a Fuji No. 7 filter (trademark) (red filter through which rays having a long Wavelength of about 580 nm. penetrate, produced by Fuji Photo Film Co., Ltd.) and subjected to development.
- As the developing solution that having a composition described in Table l was used,
- Table 2 shows the red sensitivity and maximum sensitization achieved employing the above-mentioned sensitizing dye (I) by itself.
- Table 3 shows the red sensitivity and maximum sensitization realized when using the abovementioned sensitizing dye (H) by itself.
- Table 4 shows the red sensitivity and maximum sensitization realized when using combinations of sensitizing dyes (I) and (II).
- sensitizing dye (10- molslkg. emulsion) (ml.) Emulsion Maximum sensitization Red tnm.) sensitivity oomocoemoemeeeomoooeoo Red sensitivity is shown as the relative sensitivity based on the red sensitivity of sensitizing dye B being 100 when exposed using Fuji No. 7 filter (red filter).
- R and R each represents a lower alkyl group or a substituted lower alkyl group
- Z and Z each represents an atomic group necessary to complete a benzothiazole nucleus, a benzoselenazole nucleus or a naphthothiazole nucleus
- X represents an anion
- R represents a lower alkyl group and R R Z Z X and m each has the same meaning as R R Z Z X and 11, respectively.
- sensitizing dye (II) is a compound selected from the group consisting of 5.
- the silver halide light-sensitive photographic emulsion as claimed in claim 1 further comprising at least one pseudocyanine dye.
- a light-sensitive photographic material comprising a support having coated thereon at least one layer containing the silver halide light-sensitive photographic emulsion as claimed in claim 1.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45011586A JPS4842173B1 (enrdf_load_stackoverflow) | 1970-02-10 | 1970-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3677765A true US3677765A (en) | 1972-07-18 |
Family
ID=11781995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US114338A Expired - Lifetime US3677765A (en) | 1970-02-10 | 1971-02-10 | Silver halide supersensitized photographic emulsion |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3677765A (enrdf_load_stackoverflow) |
| JP (1) | JPS4842173B1 (enrdf_load_stackoverflow) |
| BE (1) | BE762770A (enrdf_load_stackoverflow) |
| CA (1) | CA975605A (enrdf_load_stackoverflow) |
| DE (1) | DE2106170A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2078428A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1342532A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622290A (en) * | 1984-11-09 | 1986-11-11 | Mitsubishi Paper Mills, Ltd. | Silver halide photographic emulsion |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
-
1970
- 1970-02-10 JP JP45011586A patent/JPS4842173B1/ja active Pending
-
1971
- 1971-02-09 CA CA104,836A patent/CA975605A/en not_active Expired
- 1971-02-10 US US114338A patent/US3677765A/en not_active Expired - Lifetime
- 1971-02-10 FR FR7104436A patent/FR2078428A5/fr not_active Expired
- 1971-02-10 BE BE762770A patent/BE762770A/xx unknown
- 1971-02-10 DE DE19712106170 patent/DE2106170A1/de active Pending
- 1971-04-19 GB GB2178571A patent/GB1342532A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622290A (en) * | 1984-11-09 | 1986-11-11 | Mitsubishi Paper Mills, Ltd. | Silver halide photographic emulsion |
| 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 |
|---|---|
| DE2106170A1 (de) | 1971-08-26 |
| FR2078428A5 (enrdf_load_stackoverflow) | 1971-11-05 |
| BE762770A (fr) | 1971-07-16 |
| GB1342532A (en) | 1974-01-03 |
| CA975605A (en) | 1975-10-07 |
| JPS4842173B1 (enrdf_load_stackoverflow) | 1973-12-11 |
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