US3177078A - Filter and absorbing dyes for photographic emulsions - Google Patents
Filter and absorbing dyes for photographic emulsions Download PDFInfo
- Publication number
- US3177078A US3177078A US253003A US25300363A US3177078A US 3177078 A US3177078 A US 3177078A US 253003 A US253003 A US 253003A US 25300363 A US25300363 A US 25300363A US 3177078 A US3177078 A US 3177078A
- Authority
- US
- United States
- Prior art keywords
- colour
- silver halide
- sensitive
- spectrum
- red
- 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 claims description 43
- 239000000975 dye Substances 0.000 title description 14
- 229910052709 silver Inorganic materials 0.000 claims description 35
- 239000004332 silver Substances 0.000 claims description 35
- -1 SILVER HALIDE Chemical class 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000001228 spectrum Methods 0.000 claims description 11
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- QINGEILZLSOMTB-UHFFFAOYSA-N 1,2-diaminonaphthalene-1,2-disulfonic acid Chemical compound NC1(C(C=CC2=CC=CC=C12)(S(=O)(=O)O)N)S(=O)(=O)O QINGEILZLSOMTB-UHFFFAOYSA-N 0.000 claims description 2
- ORWQBKPSGDRPPA-UHFFFAOYSA-N 3-[2-[ethyl(methyl)amino]ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(C)CC)=CNC2=C1 ORWQBKPSGDRPPA-UHFFFAOYSA-N 0.000 claims 4
- 239000000463 material Substances 0.000 description 15
- 229920000159 gelatin Polymers 0.000 description 11
- 235000019322 gelatine Nutrition 0.000 description 11
- 239000001828 Gelatine Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 231100000489 sensitizer Toxicity 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HAUULSKNUKKCHM-UHFFFAOYSA-N 1-[(1-hydroxynaphthalene-2-carbonyl)amino]octadecane-4-sulfonic acid Chemical compound CCCCCCCCCCCCCCC(CCCNC(=O)C1=C(C2=CC=CC=C2C=C1)O)S(=O)(=O)O HAUULSKNUKKCHM-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- VRJRYYZQHXJUEW-UHFFFAOYSA-N 3,4-diaminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=C(N)C2=C1 VRJRYYZQHXJUEW-UHFFFAOYSA-N 0.000 description 1
- KHEHRJJAWUJGDW-UHFFFAOYSA-N 5,6-diaminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=C(N)C(N)=CC=C21 KHEHRJJAWUJGDW-UHFFFAOYSA-N 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- YTCQFLFGFXZUSN-BAQGIRSFSA-N microline Chemical compound OC12OC3(C)COC2(O)C(C(/Cl)=C/C)=CC(=O)C21C3C2 YTCQFLFGFXZUSN-BAQGIRSFSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
- G03C1/833—Dyes containing a metal atom
Definitions
- the sharpness and resolution of photographic images produce with photosensitive layers of silver halide emulsions are impaired by the light scattering caused by the silver halide grains. This elfect can be reduced by colouring the photosensitive layers with dyestuffs which absorb light in the spectral range to which the emulsion is sensitive, which dyestufis may then be removed after exposure.
- the harmful effect of the scattered light is attenuated owing to the longer path which the light has to traverse than the light which falls directly on the silver halide granules to produce the image.
- Dyestuffs particularly when used for colour photography, must be practically completely decolorised or removed subsequently because even a faint stain of residual dyestuif can considerably impair the quality of a colour image.
- Many dyestuffs which are decolorised by the agents used in the processing baths, e.g., by sodium sulphite or potassium ferricyanide are useless because mostly the decolorisation is incomplete. It is therefore advantageous to use dyestuffs which can be washed out of gelatine layers.
- Dyestuffs which are suitable for absorbing the scattered light particularly in the red sensitive layer of multiple layer photographic materials without having a desensitising action and which may be removed quantitatively from gelatine layers by washing with water are by far rarer than absorbing dyestuffs for the layers which are sensitive' to green or blue.
- red sensitive layer dyestufis which are easily soluble in water, particularly for colour photographic multi-layer copying materials which have a strong absorp- 'tive action in the whole red region of therspectrum, especially in the region of maximum red sensitivity, which.
- the absorbing dyestuffs according to the invention are added in aqueous solution, preferably in quantities of 0.5 to 5 grams per gram atom of silver in the form of silver halide to the gelatine-silver halide emulsions before casting. Based on the quantity of silver halide in the emulsion, we have found that for about 0.5 to about 10 g. of dye per gram mole of silver can be employed, although higher or smaller amounts of dye can be used depending upon particular conditions.- Owing to the high watersolubility of the dyestuifs and their low aflinity to gelatines they become distributed over adjacent layers so that it may be advantageous to colour not only the red sensitive emulsion layer but also the other emulsion layers before casting.
- the dyestuffs which are uniformly distributed in all the layers, in addition reduce the intensity of reflected light.
- FIGURE 1 shows the preparation and application of the dyestufis (A, B, C) according to the invention.
- FIGURE 2 shows the spectral distribution of red-sensitivity of the photographic layer sensitised with dyestuff Rr 1953 (Fiat Final Report No. 943), with themain maximum of red sensitisation in the region between 680 and 710 III/1., which is characteristic for multi-layer copying materials for colour photography.
- Rr 1953 conforms to the following formula:
- Example 1 31.8 g. of 1,2-diaminonaphthalene-3,7-disulphonic acid was dissolved by gently heating it in ml. of water and adding 80 ml. saturated sodium acetate solution. 32.4.g. of ferric chloride dissolved in 100 m1. of water were then gradually added with stirring at'30 C. to the yellow solution. After allowing the mixture to stand at room temperature for one hour, the" precipitated dyestulf (A) was isolated by suction filtering and digested twice with a small quantity of 1 5% hydrochloric acid and then filtered by suction until dry in air and subsequently completely dried at 70. 12 g. of dark green powder readily soluble in water to give a clear'solution with a brilliant blue-green colour were obtained.
- This emulsion was used for the middle layer of a three.
- the lowest layer applied on a cellulose triacetate foil consisted of a blue sensitive gelatine-si-lver bromide emulsion with yellow colour coupler, andthe uppermost layer was a green sensitive gela-.
- tine-silver chlorobromide emulsion with magenta colour coupler contained about 42 mg. of dyestufi (A) per mP. film was composed without the addition of absorbing dyestuff.
- Example 2 50 g. of 1,Z-diaminonaphthalene-S,7-disulphoni-c acid was dissolved by heatingin 350 ml. of water and 49 g. potassium acetate were added. 170 cc. of a 3 1% ferric chloride solution were stirred at into this intensely coloured yellow solution. After stirring for one hour at room temperature, the precipitated dyestuff (B) was filtered off by suction, pu-rifiedby digesting with 20%.
- a three layer positive colour-film was built up as in Example 1, except that all the layers contained 0.6 g.
- V Example 3 V 35.4 g; l,Z-diaminonaphthalene-f;,6-disulphonio. acid used such as cyanmes, 'merocyanines, complex (trinuclear) and 29.4 g. potassium acetate were dissolved together in 200 ml. water. 32 g. of ferric chloride dissolved in 100 ml. water were added at 35 with stirring.
- the product was filtered after 15 'minutes and the filtrate was treated with 1 /2 times its volume of alcohol and the precipitated dyestufi (C) was separated by suction filtration, washed with about 50 ml. of 96% alcoholand dried in a drying oven at 70. 37v g. of a greenishblack powder readily soluble in water to give a clearblue green solution were'obtained.
- the photographic. silver halideemulsions can be optically sensitised or unsensitised-
- Emulsions ofsilver chloride'orsilver chloro bromide are. preferred.
- our invention is particularly directed to .the ordinary employed silver halide gelatine emulsions, binding agents other than .gelatine, e.g.',' polyvinyl alcohol or. cellulose materials; .such 1 as hydrolyzed cellulose acetate; carboxymethyl. cellulose I or the like which haveno; deleterious etlect upon the lightsensitive materials, can beemployed aloneor in comb1nation.with.gelatine;. i g
- the emulsions prepared in accordance with our inven- 'tion can. be coated in the usual manner uponany suitable material with absorbing dyestuft had a resolution of p I lines/mm. and much better contrast.
- the blue-green colour-coupler used in the emulsion according to the invention is not especially critical and is selected according to the requirements of the particular copying material in which the emulsion is to be used.
- a photographic silver halide gelatine emulsion optically sensitised to the red region of the spectrum containing from about 0.5 to 10 g. per mole of silver halide of a water soluble dye, said dye being a reaction product of ferric chloride with 1,2-diaminonaphthalene disulphonic acids, said reaction product having its maximum absorption in the red region of the spectrum.
- a photographic element for subtractive colour photography comprising a support having coated thereon a plurality of silver halide emulsion layers, one of which is sensitive to the blue region of the spectrum and contains a colour-forming compound capable of coupling with the oxidation products of a colour developer to produce a yellow image, one of which is sensitive to the green region of the spectrum and contains a colour-forming compound capable of coupling with the oxidation products of a colour developer to produce a magenta image and one of which is sensitive to the red region of the spectrum and contains (1) a colour-forming compound capable of coupling with the oxidation products of a colour developer to produce a cyan image and 2) from about 0.5 to 10- grams per mole of silver halide of a water soluble dye having its maximum absorption in the red-light region of the spectrum, said dye being a reaction product of ferric chloride with 1,2-diamiuonaphthalene-disulphonic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA39366A DE1152609B (de) | 1962-02-03 | 1962-02-03 | Photographisches Material und rotempfindliche Halogensilberemulsion, insbesondere infarbphotographischen Mehrschichtenmaterialien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3177078A true US3177078A (en) | 1965-04-06 |
Family
ID=6931329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US253003A Expired - Lifetime US3177078A (en) | 1962-02-03 | 1963-01-21 | Filter and absorbing dyes for photographic emulsions |
Country Status (5)
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409433A (en) * | 1963-07-15 | 1968-11-05 | Agfa Ag | Photographic materials containing filter dyes |
| US3531287A (en) * | 1967-01-16 | 1970-09-29 | Eastman Kodak Co | Color separation film containing light-absorbing dye |
| US3547640A (en) * | 1967-03-09 | 1970-12-15 | Eastman Kodak Co | Multicolor photographic elements |
| US4542087A (en) * | 1984-09-04 | 1985-09-17 | Eastman Kodak Company | Use of reflecting agent in yellow dye image-providing material layer |
| EP0200502A2 (en) | 1985-04-30 | 1986-11-05 | Konica Corporation | Light-sensitive silver halide color photographic material |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| US5139930A (en) * | 1984-04-20 | 1992-08-18 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic light-sensitive material |
| US5561028A (en) * | 1994-06-24 | 1996-10-01 | Mitsubishi Paper Mills Limited | Silver halide photographic photosensitive material |
| WO2007114196A1 (ja) | 2006-03-28 | 2007-10-11 | Fujifilm Corporation | 導電膜及びその製造方法、並びに透光性電磁波シールド膜 |
| WO2008038764A1 (en) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Spontaneous emission display, spontaneous emission display manufacturing method, transparent conductive film, electroluminescence device, solar cell transparent electrode, and electronic paper transparent electrode |
| WO2008075771A1 (ja) | 2006-12-21 | 2008-06-26 | Fujifilm Corporation | 導電膜およびその製造方法 |
| EP1975698A1 (en) | 2007-03-23 | 2008-10-01 | FUJIFILM Corporation | Method and apparatus for producing conductive material |
| EP2009977A2 (en) | 2007-05-09 | 2008-12-31 | FUJIFILM Corporation | Electromagnetic shielding film and optical filter |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01274131A (ja) * | 1988-04-27 | 1989-11-01 | Konica Corp | 高感度かつ硬調なハロゲン化銀写真感光材料 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1163100A (fr) * | 1955-10-17 | 1958-09-22 | Kodak Pathe | Nouvelle émulsion photosensible |
-
0
- BE BE627808D patent/BE627808A/xx unknown
-
1962
- 1962-02-03 DE DEA39366A patent/DE1152609B/de active Pending
-
1963
- 1963-01-15 CH CH48063A patent/CH436978A/de unknown
- 1963-01-21 US US253003A patent/US3177078A/en not_active Expired - Lifetime
- 1963-02-01 GB GB4285/63A patent/GB986840A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1163100A (fr) * | 1955-10-17 | 1958-09-22 | Kodak Pathe | Nouvelle émulsion photosensible |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409433A (en) * | 1963-07-15 | 1968-11-05 | Agfa Ag | Photographic materials containing filter dyes |
| US3531287A (en) * | 1967-01-16 | 1970-09-29 | Eastman Kodak Co | Color separation film containing light-absorbing dye |
| US3547640A (en) * | 1967-03-09 | 1970-12-15 | Eastman Kodak Co | Multicolor photographic elements |
| US5139930A (en) * | 1984-04-20 | 1992-08-18 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic light-sensitive material |
| US4542087A (en) * | 1984-09-04 | 1985-09-17 | Eastman Kodak Company | Use of reflecting agent in yellow dye image-providing material layer |
| EP0200502A2 (en) | 1985-04-30 | 1986-11-05 | Konica Corporation | Light-sensitive silver halide color photographic material |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| US5561028A (en) * | 1994-06-24 | 1996-10-01 | Mitsubishi Paper Mills Limited | Silver halide photographic photosensitive material |
| WO2007114196A1 (ja) | 2006-03-28 | 2007-10-11 | Fujifilm Corporation | 導電膜及びその製造方法、並びに透光性電磁波シールド膜 |
| WO2008038764A1 (en) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Spontaneous emission display, spontaneous emission display manufacturing method, transparent conductive film, electroluminescence device, solar cell transparent electrode, and electronic paper transparent electrode |
| WO2008075771A1 (ja) | 2006-12-21 | 2008-06-26 | Fujifilm Corporation | 導電膜およびその製造方法 |
| EP1975698A1 (en) | 2007-03-23 | 2008-10-01 | FUJIFILM Corporation | Method and apparatus for producing conductive material |
| EP2009977A2 (en) | 2007-05-09 | 2008-12-31 | FUJIFILM Corporation | Electromagnetic shielding film and optical filter |
Also Published As
| Publication number | Publication date |
|---|---|
| CH436978A (de) | 1967-05-31 |
| GB986840A (en) | 1965-03-24 |
| BE627808A (US06262066-20010717-C00359.png) | |
| DE1152609B (de) | 1963-08-08 |
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