US3929484A - Color developer compositions containing improved yellow dye-forming coupler - Google Patents
Color developer compositions containing improved yellow dye-forming coupler Download PDFInfo
- Publication number
- US3929484A US3929484A US492116A US49211674A US3929484A US 3929484 A US3929484 A US 3929484A US 492116 A US492116 A US 492116A US 49211674 A US49211674 A US 49211674A US 3929484 A US3929484 A US 3929484A
- Authority
- US
- United States
- Prior art keywords
- coupler
- yellow
- color
- dye
- developer compositions
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 13
- -1 AMINO Chemical class 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001768 cations Chemical class 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 239000001043 yellow dye Substances 0.000 abstract description 5
- 230000032683 aging Effects 0.000 abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000008366 buffered solution Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JEOQACOXAOEPLX-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)C1CSCN1.OC(=O)[C@@H](N)CCCN=C(N)N JEOQACOXAOEPLX-WCCKRBBISA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- FFAJEKUNEVVYCW-UHFFFAOYSA-N 4-n-ethyl-4-n-(2-methoxyethyl)-2-methylbenzene-1,4-diamine Chemical group COCCN(CC)C1=CC=C(N)C(C)=C1 FFAJEKUNEVVYCW-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical group C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ATGAWOHQWWULNK-UHFFFAOYSA-I pentapotassium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [K+].[K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O ATGAWOHQWWULNK-UHFFFAOYSA-I 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30535—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site not in rings of cyclic compounds
-
- 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
- Y10S430/149—Lippmann
Definitions
- ABSTRACT Color developer compositions which contain, dissolved therein, both (a) an organic aromatic primary amino developing agent and (b) a yellow-dye-forming coupler having the structure:
- R is a branched alkyl group containing 3 to 6 carbon 10 atoms; X is C1 or Br; Y is X, hydrogen or I alkyl (1 to 8 carbon atoms); and A and B differ and are either H or -COOM, wherein M is a photographically inactive cation or a methyl or ethyl group.
- Use of such compositions results in more efficient coupler usage and color products having yellow dyes with improved aging characteristics.
- the invention encompasses such liquid developer compositions, blends of (a) and (b), and the yellow dye-forming couplers, per
- the present invention relates to developer compositions containing such valuable diffusible yellow-dye-forming coupler materials.
- the coupler compounds of this invention are haloanilidophenoxycarboxy compounds having the structure I:
- R is a branched alkyl group containing 3 to 6 carbon atoms: X is Cl or Br; Y is X, hydrogen or alkyl (1 to 8 carbon atoms); and A and B differ and are either H or -COOM, wherein M is a photographically inactive cation, a methyl group or an ethyl group.
- This invention also includes developer compositions containing one or more of the compounds ofthe structure I l and one or more organic aromatic amino developing agents, which developer compositions are used in the form of aqueous solutions comprising water and having a pH ofat least about 10.
- color-forming coupler compounds have been classified as incorporated" and diffusible", based upon the way such compounds are ordinarily used.
- incorporated couplers have fairly large molecules in order to prevent the diffusion or substantial movement of such couplers within the particular hydrophilic colloid layer into which they were incorporated during the manufacture of the photographic element.
- diffusible' couplers are soluble in alkaline solutions which also usually contain one or more organic aromatic amino developing agents.
- diffusible couplers when diffusible couplers are used, their capability ofdiffusing into (and through) the emulsion layers of the photographic element being treated makes it possible for them to react (couple) with oxidized aromatic amino color developer(s) and thereby become effectively bound into the emulsion layer. In this situation. unreacted diffusible coupler can be readily removed from the photographic element via simply washing the element with water.
- Diffusible couplers that form yellow dyes have, to date, exhibited more of a need in this respect than have other types of color-forming couplers.
- couplers (and compositions containing them) of the present invention apparently result from the unique combination of substituents on the basic ketomethylene backbone structure of the coupler compounds encompassed by Formula I above.
- couplers having a. an aryloxy coupling of group attached through the ether linkage directly to the active carbon atom of the coupler and b. a branched alkyl group (such as R in structure I above) attached to one of the activating carbonyl groups in an acetanilide coupler.
- HY DROLYTIC STABILITY TEST As it was stated above, one of the valuable properties of the materials of the present invention relates to their surprisingly highresistance to hydrolysis under conditions which simulate end-use conditions; namely, in aqueoussolution at a buffered pH of 12.06 and at a temperature of 239C. Under such conditions, with the coupler being dissolved in the aqueous buffered solution at a concentration of coupler about 6.6 X 10' molar, many couplers have been found to degrade (hydrolyze) at varying rates of hydrolysis. The rates of hydrolysis are apparently unaffected by the presence or absence of color developing agent in the solution.
- compositionsof the-present invention comprise one or more p.-'phenylenedia mine type color developing agents.
- Such agents are well known an'dneed not be described in detail herein, since any phenylenediamine color developing-agent .can be'used.
- a preferred pphenylenediamine-type color developing agent is 4- amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine, di-ptoluenesulfonate salt.
- the coupler compounds of structure I can be used successfully in combination with such color developing agents. The ratio of color develinthis test.
- the coupier/color developer compositions of this invention are preferably' b'lends of solid ,icr-ystalline or powdered materials whichb-lendscanreadily be dissolved in aqueous compositions in the preparation of color developer bziths:
- Such baths which contain yellow dye-forming 2'5 coupler dissolved therein, can then be used in the conventional manner during the yellow developer step in a multi-step process for manufacturing colored pho- EXAMPLE
- a conventional photographic element comprising a Data resulting fromqsubjeeting the processed film strips to spectrophotometric absorption tests were recorded.
- Couplers providing data for Table II were so-called fourequivalent-couplers, while those providing data for Table lIl were two-equivalent" couplers.
- Substituent groups appearing at the column headings in these Tables refer to the structural formula at the beginning of each table. 1
- Coupler Material O H O CO2CH2C6H5 A solution of 76.9 g of the amide (I) and phenol(ll) times with 100 ml water and then dried over M SO in 400 ml of acetonitrile containing 30.1 g. triethylam- 55 filtered, and concentrated in vacuum. The resulting ine was heated at reflux for 2 /2 hours. The solution was yellow syrup was dissolved in 200 ml methanol and then evaporated in vacuum. The resulting solid matecrystallized at room temperature. The dried crystalline rial was dissolved in 500 ml chloroform, extracted 3 product had a melting point of 92-95C.
- Step 2 O H O H2/Pd 1
- a solution of 51.4 g of the product from Step 1, above, in 300 ml ethyl acetate and 2.0 g of 10% palladium on carbon was shaken under 40 psi of hydrogen until hydrogen uptake ceased. Then the solution was warmed to completely dissolve the product. The resulting suspension was filtered to remove catalyst, and the filtrate was dried. The pale, pink solid material was recrystalized twice with methanol containing charcoal (for color improvement) to yield a product (Compound lV) having a melting point of l85l87.5C.
- a color developer composition comprising at least one organic aromatic primary amino developing agent and a yellow-dye-forming coupler material; the improvement which comprises using as said yellowdye-forming coupler material a compound having the structure:
- R is a branched alkyl group containing 3 to 6 carbon atoms; X is Cl or Br; Y is X, hydrogen or alkyl (l'to 8 carbon atoms); and A and B differ and are either H or COOM, wherein M is a photographically inactive cation or a methyl or ethyl group.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US492116A US3929484A (en) | 1974-03-08 | 1974-07-26 | Color developer compositions containing improved yellow dye-forming coupler |
| CA219,819A CA1041116A (en) | 1974-03-08 | 1975-02-11 | Color developer compositions containing improved yellow dye-forming coupler |
| JP2642975A JPS559697B2 (enrdf_load_stackoverflow) | 1974-03-08 | 1975-03-04 | |
| DE19752510075 DE2510075C3 (de) | 1974-03-08 | 1975-03-07 | Farbentwickler für farbphotographische Aufzeichnungsmaterialien |
| IT21050/75A IT1034108B (it) | 1974-03-08 | 1975-03-07 | Composti copulanti formanti colo ranti e compositioni di contengono |
| CH294275A CH593500A5 (enrdf_load_stackoverflow) | 1974-03-08 | 1975-03-07 | |
| FR7507135A FR2263537B1 (enrdf_load_stackoverflow) | 1974-03-08 | 1975-03-07 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44980074A | 1974-03-08 | 1974-03-08 | |
| US492116A US3929484A (en) | 1974-03-08 | 1974-07-26 | Color developer compositions containing improved yellow dye-forming coupler |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/583,340 Division US3994967A (en) | 1974-03-08 | 1975-06-02 | Color developer compositions containing improved yellow dye-forming coupler |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3929484A true US3929484A (en) | 1975-12-30 |
Family
ID=27035819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US492116A Expired - Lifetime US3929484A (en) | 1974-03-08 | 1974-07-26 | Color developer compositions containing improved yellow dye-forming coupler |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3929484A (enrdf_load_stackoverflow) |
| JP (1) | JPS559697B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1041116A (enrdf_load_stackoverflow) |
| CH (1) | CH593500A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2263537B1 (enrdf_load_stackoverflow) |
| IT (1) | IT1034108B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394440A (en) * | 1982-01-22 | 1983-07-19 | Eastman Kodak Company | Yellow-dye-forming photographic developing composition |
| US4828970A (en) * | 1986-04-18 | 1989-05-09 | Konishiroku Photo Industry Co., Ltd. | Method for processing a light-sensitive silver halide color photographic material by controlling the pH value of the bleach fixing solution |
| US4882264A (en) * | 1984-01-20 | 1989-11-21 | Olin Hunt Specialty Products Inc. | Color developer composition |
| 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 |
Families Citing this family (7)
| 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 |
| AU570081B2 (en) | 1983-11-02 | 1988-03-03 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material |
| JPS60143331A (ja) | 1983-12-29 | 1985-07-29 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| AU590563B2 (en) | 1985-05-16 | 1989-11-09 | Konishiroku Photo Industry Co., Ltd. | Method for color-developing a silver halide color photographic light-sensitive material |
| DE3681347D1 (de) | 1985-05-31 | 1991-10-17 | Konishiroku Photo Ind | Verfahren zur herstellung eines direkt positiven farbbildes. |
| DE3682128D1 (de) | 1985-07-17 | 1991-11-28 | Konishiroku Photo Ind | Photographisches silberhalogenidmaterial. |
| AU591540B2 (en) | 1985-12-28 | 1989-12-07 | Konishiroku Photo Industry Co., Ltd. | Method of processing light-sensitive silver halide color photographic material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277155A (en) * | 1960-08-24 | 1966-10-04 | Eastman Kodak Co | Monofluoro-beta-ketoacetanilide couplers for color photography |
| US3770446A (en) * | 1970-12-18 | 1973-11-06 | Konishiroku Photo Ind | Color photographic silver halide material containing acetanilide couplers |
-
1974
- 1974-07-26 US US492116A patent/US3929484A/en not_active Expired - Lifetime
-
1975
- 1975-02-11 CA CA219,819A patent/CA1041116A/en not_active Expired
- 1975-03-04 JP JP2642975A patent/JPS559697B2/ja not_active Expired
- 1975-03-07 FR FR7507135A patent/FR2263537B1/fr not_active Expired
- 1975-03-07 IT IT21050/75A patent/IT1034108B/it active
- 1975-03-07 CH CH294275A patent/CH593500A5/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277155A (en) * | 1960-08-24 | 1966-10-04 | Eastman Kodak Co | Monofluoro-beta-ketoacetanilide couplers for color photography |
| US3770446A (en) * | 1970-12-18 | 1973-11-06 | Konishiroku Photo Ind | Color photographic silver halide material containing acetanilide couplers |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394440A (en) * | 1982-01-22 | 1983-07-19 | Eastman Kodak Company | Yellow-dye-forming photographic developing composition |
| US4882264A (en) * | 1984-01-20 | 1989-11-21 | Olin Hunt Specialty Products Inc. | Color developer composition |
| 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 |
| US4828970A (en) * | 1986-04-18 | 1989-05-09 | Konishiroku Photo Industry Co., Ltd. | Method for processing a light-sensitive silver halide color photographic material by controlling the pH value of the bleach fixing solution |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS559697B2 (enrdf_load_stackoverflow) | 1980-03-11 |
| CH593500A5 (enrdf_load_stackoverflow) | 1977-12-15 |
| FR2263537A1 (enrdf_load_stackoverflow) | 1975-10-03 |
| IT1034108B (it) | 1979-09-10 |
| FR2263537B1 (enrdf_load_stackoverflow) | 1977-04-15 |
| DE2510075B2 (de) | 1977-03-10 |
| JPS50123342A (enrdf_load_stackoverflow) | 1975-09-27 |
| CA1041116A (en) | 1978-10-24 |
| DE2510075A1 (de) | 1975-09-11 |
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