US3784383A - Light sensitive silver halide color photographic material - Google Patents
Light sensitive silver halide color photographic material Download PDFInfo
- Publication number
- US3784383A US3784383A US00256010A US3784383DA US3784383A US 3784383 A US3784383 A US 3784383A US 00256010 A US00256010 A US 00256010A US 3784383D A US3784383D A US 3784383DA US 3784383 A US3784383 A US 3784383A
- Authority
- US
- United States
- Prior art keywords
- coupler
- silver halide
- color photographic
- light
- photographic material
- 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
- 239000000463 material Substances 0.000 title claims abstract description 38
- -1 silver halide Chemical class 0.000 title claims description 26
- 229910052709 silver Inorganic materials 0.000 title claims description 25
- 239000004332 silver Substances 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 230000002950 deficient Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000009102 absorption Effects 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000000873 masking effect Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 241000689227 Cora <basidiomycete fungus> Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture 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
- 239000002904 solvent Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- BYGOPQKDHGXNCD-UHFFFAOYSA-N tripotassium;iron(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] BYGOPQKDHGXNCD-UHFFFAOYSA-N 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
- G03C7/32—Colour coupling substances
- G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
- G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
Definitions
- color photographic material containing a cyan coupler discloses couplers of the formula usable in the form of a solution in an organic solvent, Y
- cyan coupler providing auto-masking mechanism for the light-sensitive color photographic material so as OH to compensate for the deficient color reproductivity of A I said material.
- CONHR' Almost all of the cyan couplers used as color formers in light-sensitive color photographic materials are compounds of the l-naphthol-Z-carboxylic acid or orthoaminophenol type.
- cyan colored couplers having an arylazo group at their 4-position have been utilized as colored couplers provided with autornasking mechanism so as to compensate for deficiencies in color reproductivityofcolor photographic materials concerned.
- the above-mentioned couplers have less of a disadvantage with respect to spectral absorption but are extremely low (about one-half) in emulsion speed as compared with the coupler (I) and inferior in graininess of the resulting color images.
- the protected type colored cyan couplers of Japanese Pat. Publication No. l 1,304/1967 are used for negative sensitive materials. It is therefore desirable that couplers have such properties that they are excellent in solubility in organic solvents, favorable in auto-masking effects (broad in the range of isospecific points of blue and green portions), high in speed and prominent in graininess of the resulting images.
- Couplers having all such properties have, of course, not been provided hitherto, but the coupler (I) has many desirable properties.
- the coupler (I) is actually dissolved in an organic solvent such as tricresyl phosphate or the like and is finely dispersed in an aqueous gelatin solution, the resulting dispersion is somewhat low in stability and the dispersed particles frequently unite with each other when the dispersion is allowed to stand for a long time.
- the COCH of the arylazo group is varied to --COC H -COC H-, or the like, no substantial change is seen in solubility.
- there is a new disadvantage that if said --COCH is varied to COC H the coupler (1) brings about a marked color variation when subjected to ordinary color development and becomes unusable in practice.
- the present invention provides couplers which are free from the above-mentioned disadvantages.
- the present invention is concerned with lightsensitive silver halide color photographic materials characterized by containing a coupler having the formula ( ⁇ OCONH(CHz) 0tC H N II N I COOR wherein n is an integer of l to 4, and R is a lower alkyl group.
- the reaction mixture was charged into 25 liters of water, and the deposited red crystals were recovered by filtration. After washing with water, the crystals were dried and then recrystallized from 55 liters of npropanol to form a red powder.
- This red powder was washed with 300 ml. of methanol and then dried to obtain 750 g. of l-hydroxy-4-(2-carboethoxyphenylazo- N-[ 8-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide, coupler (l), as a red powder. m.p. 169 170C., yield 92 percent.
- Test Example 1 The couplers used in the present invention and other couplers were compared to each other in solubility for tricresyl phosphate in such a manner that 1 g. of each coupler was dissolved at 80C. in tricresyl phosphate and then allowed to stand at 20C., and the time required for initiation of the crystallization of said coupler was measured to obtain the results as shown below.
- Couplers of the present invention which were of the formula shown below and the known coupler of the same formula, except that R' was different, were tested for solubility in a high boiling solvent to obtain the re- 1 sults set forth in the table below.
- One gram of each coupler was thoroughly dissolved in tricresyl phosphate and the solubility thereof was represented by the minimum amount (cc.) of the tricresyl phosphate in which .the coupler did not deposit at room temperature for more than 24 hours.
- the couplers e mployed in the present invention may be optionally varied in solubility. Moreover, all these 2 couplers are excellent in emulsion property and masking property, and they always give light-sensitive color photographic materials having uniform photographic properties.
- Example 1 minute to prepare a coupler dispersion 13.5 Parts of this dispersion were added with stirring at 35C. to 100 parts of a light-sensitive silver iodobromide emulsion containing a red light-sensitive sensitizing dye, and the resulting mixture was coated on a film support and then dried to obtain a red light-sensitive color photographic material.
- the photographic material was bleached and fixed by use of a bleaching solution and a fixingsolution of the compositions shown below to remove undeveloped silver halide and by-produced reduced silver.
- Example 2 A mixture comprising 1 part of the coupler (3) and 3 parts of l-hydroxy-N-[6-(2.,4-di-t-amylphen0xy)- butyl]-2-naphthamide was dissolved with stirring at C. in 10 parts ofT.C.P., and was added to parts of a 10 percent aqueous gelatin solution kept at 60C., and the mixed solution was charged with 2 parts of a 10 percent aqueous sodium alkylbenzene-sulfonate solution. Subsequently, the liquid was. stirred at about 65C. for 5 minutes by use of a high speed rotary mixer. This procedure was repeated 5 times at intervals of 1 minute to prepare a coupler dispersion.
- This photographic material was exposed to red light through an optical wedge and was color-developed, bleached and fixed in the same manner as in Example 1, whereby a cyan colored negative image and an excellent red positiveimage were obtained simultaneously. Transparency also was quite excellent.
- Example 3 A mixture comprising 0.3 part of the coupler (1), 0.7 part of the coupler (6) and 3 parts of 1-hydroxy-N-[8- (2,4-di-t-amylphenoxy )-butyl ]-2-naphthamide was treated in the same manner as in Example 2 to obtain a red light-sensitive color photographic material. This photographic material was exposed to red light and then treated in the same manner as in Example 2, whereby a cyan colored negative image and an excellent red positive image were obtained simultaneously.
- Example 5 This experiment was conducted to compare the photographic properties of a cyan coupler according to the present invention with three cyan couplers of the prior art having a closely related structure.
- Control coupler D (Coupler lll, U.S. Pat. No.
- coupler (1) is much v at 440 my and 500 mu, as shown below:
- coupler (1) is very preferred for material as claimed in claim 1, wherein said coupler is auto-masking mechanism when it is jointly used with a a compound of the following structure colorless coupler.
- coupler (1) over coupler C results from the on structural difference between the two, in that the azo portion of coupler (I) is of the ester (COOC H5) A comucnmo uwum type whereas that of coupler C is of the ketone @5 -cocn type.
- coupler B In both coupler (l) and the coupler B; the azo portions are of the ester (-COOR) type, which show good 'l spectral characteristics.
- coupler B disadvanl tageously has undesired spectral absorption of masking -COOC2H5 dye, which is due to the inclusion of a branched alkyl group.
- the emulsion test indicates that coupler B has a broad absorption comprising two absorption maxima silver halide col or photographic material as claimed in claim 1, wherein said coupler is a compound of the following structure COOCHa wavel engtb. (m u) This means that coupler B is not appropriate as colored cyan coupler because its maskingaction is too excessive in the short wavelength region.
- coupler (l) and coupler D which have the azo portion of the ester type are equally competent in pho- 0 tographic properties.
- coupler D is detrimentally undesirable because of its having a maximum absorption at a verylong wavelength site, i.e., 720 mp. K/
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44028287A JPS4817889B1 (enrdf_load_stackoverflow) | 1969-04-14 | 1969-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3784383A true US3784383A (en) | 1974-01-08 |
Family
ID=12244380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00256010A Expired - Lifetime US3784383A (en) | 1969-04-14 | 1972-05-23 | Light sensitive silver halide color photographic material |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3784383A (enrdf_load_stackoverflow) |
| JP (1) | JPS4817889B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2017625A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1255111A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996055A (en) * | 1973-12-21 | 1976-12-07 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4138258A (en) * | 1974-08-28 | 1979-02-06 | Fuji Photo Film Co., Ltd. | Multi-layered color photographic materials |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3034892A (en) * | 1958-10-27 | 1962-05-15 | Eastman Kodak Co | Magenta-colored cyan-forming couplers |
| US3459552A (en) * | 1965-02-03 | 1969-08-05 | Fuji Photo Film Co Ltd | Silver halide emulsions containing magenta-colored cyan couplers |
| US3481741A (en) * | 1964-09-10 | 1969-12-02 | Fuji Photo Film Co Ltd | Photographic silver halide elements containing magenta-colored cyanforming couplers |
| US3583971A (en) * | 1966-07-25 | 1971-06-08 | Makoto Yoshida | 1-hydroxy-4-(alkoxycarbonylphenylazo) 2-(n-naphthyl)naphthamides |
| US3642485A (en) * | 1968-08-26 | 1972-02-15 | Fuji Photo Film Co Ltd | Color-photographic silver halide materials containing colored and uncolored couplers |
| US3667956A (en) * | 1969-02-24 | 1972-06-06 | Light-sensitive silver halide color photographic materials containing cyan couplers |
-
1969
- 1969-04-14 JP JP44028287A patent/JPS4817889B1/ja active Pending
-
1970
- 1970-04-13 DE DE19702017625 patent/DE2017625A1/de active Pending
- 1970-04-14 GB GB07796/70A patent/GB1255111A/en not_active Expired
-
1972
- 1972-05-23 US US00256010A patent/US3784383A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3034892A (en) * | 1958-10-27 | 1962-05-15 | Eastman Kodak Co | Magenta-colored cyan-forming couplers |
| US3481741A (en) * | 1964-09-10 | 1969-12-02 | Fuji Photo Film Co Ltd | Photographic silver halide elements containing magenta-colored cyanforming couplers |
| US3459552A (en) * | 1965-02-03 | 1969-08-05 | Fuji Photo Film Co Ltd | Silver halide emulsions containing magenta-colored cyan couplers |
| US3583971A (en) * | 1966-07-25 | 1971-06-08 | Makoto Yoshida | 1-hydroxy-4-(alkoxycarbonylphenylazo) 2-(n-naphthyl)naphthamides |
| US3642485A (en) * | 1968-08-26 | 1972-02-15 | Fuji Photo Film Co Ltd | Color-photographic silver halide materials containing colored and uncolored couplers |
| US3667956A (en) * | 1969-02-24 | 1972-06-06 | Light-sensitive silver halide color photographic materials containing cyan couplers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996055A (en) * | 1973-12-21 | 1976-12-07 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4138258A (en) * | 1974-08-28 | 1979-02-06 | Fuji Photo Film Co., Ltd. | Multi-layered color photographic materials |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1255111A (en) | 1971-11-24 |
| DE2017625A1 (de) | 1970-10-22 |
| JPS4817889B1 (enrdf_load_stackoverflow) | 1973-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: KONICA CORPORATION, JAPAN Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302 Effective date: 19871021 |