US2521908A - 1-hydroxy-2-naphthamide colored couplers - Google Patents
1-hydroxy-2-naphthamide colored couplers Download PDFInfo
- Publication number
- US2521908A US2521908A US734548A US73454847A US2521908A US 2521908 A US2521908 A US 2521908A US 734548 A US734548 A US 734548A US 73454847 A US73454847 A US 73454847A US 2521908 A US2521908 A US 2521908A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- compound
- coupler
- prepared
- developing
- 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
- ZTXWIKHKNGFJAX-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)N)=CC=C21 ZTXWIKHKNGFJAX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 SILVER HALIDE Chemical class 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000005840 aryl radicals Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- YZJSKRBKHCLMQC-UHFFFAOYSA-N 3-hydroxy-n-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 YZJSKRBKHCLMQC-UHFFFAOYSA-N 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- BGDWGIMWXKYYOG-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C(O)=C(C(Cl)=O)C=CC2=C1 BGDWGIMWXKYYOG-UHFFFAOYSA-N 0.000 description 1
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ANGJRFQOVHLWMX-UHFFFAOYSA-M 2-ethoxycarbonylbenzenediazonium;chloride Chemical compound [Cl-].CCOC(=O)C1=CC=CC=C1[N+]#N ANGJRFQOVHLWMX-UHFFFAOYSA-M 0.000 description 1
- IXOZFDRVOFNEQB-UHFFFAOYSA-M 4-bromobenzenediazonium;chloride Chemical compound [Cl-].BrC1=CC=C([N+]#N)C=C1 IXOZFDRVOFNEQB-UHFFFAOYSA-M 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HXKYNBCJKDAHOJ-UHFFFAOYSA-N n-(3-methylbutyl)aniline Chemical compound CC(C)CCNC1=CC=CC=C1 HXKYNBCJKDAHOJ-UHFFFAOYSA-N 0.000 description 1
- NCBHMNCVLVILDH-UHFFFAOYSA-N n-(4-tert-butylphenoxy)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1ONC1=CC=CC=C1 NCBHMNCVLVILDH-UHFFFAOYSA-N 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical group 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical compound [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- KDOZVLGVHGIUFE-UHFFFAOYSA-L potassium sodium hydrogen carbonate bromide Chemical compound [Br-].[K+].C([O-])(O)=O.[Na+] KDOZVLGVHGIUFE-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C21—METALLURGY OF IRON
- C21D—MODIFYING THE PHYSICAL STRUCTURE OF FERROUS METALS; GENERAL DEVICES FOR HEAT TREATMENT OF FERROUS OR NON-FERROUS METALS OR ALLOYS; MAKING METAL MALLEABLE, e.g. BY DECARBURISATION OR TEMPERING
- C21D9/00—Heat treatment, e.g. annealing, hardening, quenching or tempering, adapted for particular articles; Furnaces therefor
- C21D9/70—Furnaces for ingots, i.e. soaking pits
Definitions
- This invention relates to color photography and particularly to color couplers for use in photographic processes.
- Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images "upon photographic development'are well known.
- these color-forming-compounds of couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporated in'the. emulsion layer and the unused coupler remains after'formation of the colored image.
- the coupler is used in the developing'solution,it may be colored without detriment to the final image" and certain colored couplers have been used in this way.
- I T N- B especially ⁇ a'mononuclear aryl radical such as phenyl or substituted phenyl, a mononuclear aryloxyphenyl radical such as p-tertiary-butylphenoiryphenyl, p-tert.-amylphenoxyphenyl, 2,4-
- d-iamylnhenoxyphenyl or phenoxypnenyl or an active po'sitionof the coupler issubstituted with an azo group --and this .group is split offi or removed by the oxidized developer when thea'zosubstituted coupler is treated with the-oxidized developer either in aqueous solution or in the photographic emulsion layer.
- the coupler may be converted to a difierently colored compound and the azo .group readily -removed;trom it by means oi :reaction wi-th the oxidized deasarpoa OOl lehydroxy-l-phenylazo-N-isoamyl-2maphthanilide 1-hydroxy-4- (2 metl1oxy-4-nitrophenylazo -N-is0amyl- 2-naphthanilide 3 C H3 00 Ha 1-hydroxy-4- [Z-methoxyl- (o-methoxyphenylazo) phenylazo] -N-isoamyl2-naphthanilide Our compounds may be incorporated either in the developing solution or in the emulsion layer according to their intended use and diffusion characteristics.
- the Hanson process involves a color correction method in which a color coupler is incorporated in the photographic emulsion layer prior to exposure and upon development is con.- verted to a colored image where theJayer is eX-- posed.
- the coupler remaining in the: unexposedportions of the layer retains itsv original color and by suitable choiceof the colorofthe original coupler and the color of the final dye image, a masking or correction effect can be obtained.
- the compounds employed according to our invention may be prepared by any suitable method such as by reaction of the naphthamide with the appropriate diazonium compound.
- compound No. 1 was prepared as follows:
- l hydroxy 4' (p-tert. butylphenoxy) -2- naphthanilide was prepared by the condensation of equi-molecular quantities of phenyl l-hydroxy-2-naphthoate and p-(p-tert-butylphenoxy-) -aniline at 200 for one hour.
- the product was purified by recrystallizationfrom a mixture of benzene and ligroin.
- the p (p-tert.-butylphenoxy) aniline was prepared by alkali condensation of hot p-nitro chlorobenzene and p-tert-butylphenol followed by catalytic reduction of the nitro compound in the presence of Raney nickel.
- Coupler Diazonium salt o-methoxybenz-ene diazonlum chloride.
- diazonium chloride 4' 1-hydroxy-4-(p-tert.-butylphe- Z-meth o xylenitronoxy) -2-naphthanilide.
- benzene diazonium f chloride 5.----- l-hydroxy-4'- (p-tert.-butylpl1e- 2-n1ethoxy4-pl1enylnoxy) -2-naphtlianilide. azobenzene diazonium chloride.
- Compound No. 6 was: prepared as follows:
- the ,4- (p-tert-.-amylphenoxy-)aniline was preparedby the condensation of hot p-nitrochlorobenzene and p-terteamylphenol in alkali to yield 4 (p tert. amylphenoxy)nitrobenzene.
- 1-- hydroxy--(o met-hoxyphenylazo)-4'-(ptert. amylphenoxy)-2-naphthanilide (6) was prepared by adding an equivalent solution of 1.05 mols of omethoxybenzene diazonium chloride to 1 mol of 1hydroxy-4-(p-tert.-amy1phenoxy)-2- naphthanilide in 8 liters of pyridine ethanol (1:1) solution at 5 C. The product was isolated by pouring the mixture into an excess of hydrochloric acid. The pure dye was obtained by crystallization from dioxane or acetic acid.
- Compound No. 8 was prepared in the following manner:
- the final compound was prepared by the simple treatment of 1 hydroxy-N- ⁇ i-[2-(2,4-diamylphenoxy) 5-(3,5-dichlorosulfonylbenzamido) benzamido] phenethyl ⁇ 2-naphthamide with benzene diazonium chloride.
- Compound 9 was prepared by the condensation in ether of two equivalents of N-methylaniline with 1 equivalent of l-hydroxy-Z-naphthoyl chloride to produce l-hydroxy-N-methyl- 2-naphthanilide.
- the final compound was prepared by treating this intermediate with o-carbethoXy-benzene diazonium chloride.
- Compound 10 was prepared by the condensation in ether of 2 equivalents of N-isoamylaniline with 1 equivalent of 1-hydroxy-2-naphthoyl chloride to produce l-hydroxy-N-isoamyl-Z- naphthanilide. This intermediate was treated with benzene diazonium chloride to produce the final compound.
- the primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols.
- the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
- Suitable compounds Grams 2-amino-5-diethyl-amino toluene HCl 2 Sodium sulphite 2 Sodium carbonate Potassium bromide 2 Water .to V1 liter.
- X is selected from the class consisting of hydrogen and alkyl radicals
- Y is selected from the class consisting of mononuclear aryl radicals and aralkyl radicals
- R is a mononuclear aryl radical
- X is selected from the class consisting of hydrogen and alkyl radicals
- Y is selected'from the class consisting of mononuclear aryl radicals and aralkyl radicals and R is a mononuclear aryl radical
- Y is a mononuclear aryl-oxyphenyl radical and R is a mononuclear aryl radical
- X is selected from the class consisting of hydrogen and alkyl radicals
- Y is selected from the class consisting of mononuclear aryl radicals, aralkyl radicals and R is a mononuclear aryl radical.
- O ONH-Y N NR Where Y and R are mononuclear aryl radicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mechanical Engineering (AREA)
- Thermal Sciences (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Developing Agents For Electrophotography (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE480525D BE480525A (en)) | 1947-03-13 | ||
| BE476362D BE476362A (en)) | 1947-03-13 | ||
| US613456A US2428054A (en) | 1945-08-30 | 1945-08-30 | Photographic color correction using colored couplers |
| FR950288D FR950288A (fr) | 1947-03-13 | 1946-08-29 | Perfectionnements à la photographie en couleurs |
| US734548A US2521908A (en) | 1947-03-13 | 1947-03-13 | 1-hydroxy-2-naphthamide colored couplers |
| GB18258/47A GB627814A (en) | 1947-03-13 | 1947-07-10 | Improvements in colour photographic development and colour-forming developers |
| FR950228D FR950228A (fr) | 1947-03-13 | 1947-07-28 | Procédé et four pour chauffer des pièces d'acier |
| CH283456D CH283456A (fr) | 1947-03-13 | 1947-12-23 | Procédé pour l'obtention d'une image colorée exempte d'argent métallique et image obtenue par ce procédé. |
| CH285169D CH285169A (fr) | 1947-03-13 | 1947-12-23 | Matériel photosensible pour la photographie en couleurs. |
| FR980372D FR980372A (fr) | 1947-03-13 | 1948-02-16 | Coupleurs colorés de la série de la 1-hydroxy-2-naphtamide |
| ES0183158A ES183158A1 (es) | 1947-03-13 | 1948-04-06 | UN PROCEDIMIENTO DE REVELADO CROMoGENO PARA LA FOTOGRAFiA EN COLORES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US734548A US2521908A (en) | 1947-03-13 | 1947-03-13 | 1-hydroxy-2-naphthamide colored couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2521908A true US2521908A (en) | 1950-09-12 |
Family
ID=24952141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US734548A Expired - Lifetime US2521908A (en) | 1945-08-30 | 1947-03-13 | 1-hydroxy-2-naphthamide colored couplers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2521908A (en)) |
| BE (2) | BE480525A (en)) |
| CH (2) | CH283456A (en)) |
| ES (1) | ES183158A1 (en)) |
| FR (3) | FR950288A (en)) |
| GB (1) | GB627814A (en)) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2706684A (en) * | 1952-11-28 | 1955-04-19 | Eastman Kodak Co | 1-hydroxy-2-naphthamide colored couplers |
| US3034892A (en) * | 1958-10-27 | 1962-05-15 | Eastman Kodak Co | Magenta-colored cyan-forming couplers |
| US3077402A (en) * | 1954-12-06 | 1963-02-12 | Polaroid Corp | Photographic color processes, products, and compositions |
| US3227550A (en) * | 1962-09-07 | 1966-01-04 | Eastman Kodak Co | Photographic color reproduction process and element |
| US3459552A (en) * | 1965-02-03 | 1969-08-05 | Fuji Photo Film Co Ltd | Silver halide emulsions containing magenta-colored cyan couplers |
| US3658545A (en) * | 1968-12-20 | 1972-04-25 | Konishiroku Photo Ind | Light-sensitive silver halide color photographic material containing cyan couplers |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0204530A2 (en) | 1985-05-31 | 1986-12-10 | Konica Corporation | Method for forming direct positive color image |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0228914A2 (en) | 1985-12-28 | 1987-07-15 | Konica Corporation | Method of processing lightsensitive silver halide color photographic material |
| US5178993A (en) * | 1990-03-01 | 1993-01-12 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic material |
| US5256772A (en) * | 1990-11-14 | 1993-10-26 | Toyo Ink Manufacturing Co., Ltd. | Monoazo lake pigment and uses thereof |
| US5286287A (en) * | 1990-10-11 | 1994-02-15 | Toyo Ink Manufacturing Co., Ltd. | Monoazo lake pigment suitable for use in printing ink and process for the production thereof |
| JPH0677141B2 (ja) | 1986-01-20 | 1994-09-28 | コニカ株式会社 | ハロゲン化銀カラ−写真感光材料 |
| 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 |
| JPH0715562B2 (ja) | 1986-01-20 | 1995-02-22 | コニカ株式会社 | ハロゲン化銀カラ−感光材料 |
| EP0711804A2 (de) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Kryptolichtschutzmittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725291A (en) * | 1952-05-01 | 1955-11-29 | Eastman Kodak Co | Azo dye couplers having two coupling nuclei |
| US2725292A (en) * | 1952-05-15 | 1955-11-29 | Eastman Kodak Co | Colored couplers containing solubilizing groups |
| US3418121A (en) * | 1964-11-11 | 1968-12-24 | Fuji Photo Film Co Ltd | Photographic developer composition containing 2-(o-propionamido-beta-phenylethyl) - 1 - hydroxynaphthamide as a color former |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2189817A (en) * | 1939-03-13 | 1940-02-13 | Du Pont Film Mfg Corp | Color-forming photographic composition, element, and process |
| GB519208A (en) * | 1938-09-17 | 1940-03-19 | John David Kendall | Improvements in or relating to colour photography |
| US2220123A (en) * | 1938-10-01 | 1940-11-05 | Bela Gaspar | Color photographic process |
| US2310943A (en) * | 1938-10-05 | 1943-02-16 | Du Pont | Polyvinyl acetals |
| US2313586A (en) * | 1939-08-24 | 1943-03-09 | Eastman Kodak Co | Hydroxynaphthoic acid amide coupler |
| US2324832A (en) * | 1940-07-16 | 1943-07-20 | Gen Aniline & Film Corp | Photographic emulsion |
| US2357394A (en) * | 1940-07-12 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2455169A (en) * | 1944-05-03 | 1948-11-30 | Eastman Kodak Co | Colored couplers |
-
0
- BE BE476362D patent/BE476362A/xx unknown
- BE BE480525D patent/BE480525A/xx unknown
-
1946
- 1946-08-29 FR FR950288D patent/FR950288A/fr not_active Expired
-
1947
- 1947-03-13 US US734548A patent/US2521908A/en not_active Expired - Lifetime
- 1947-07-10 GB GB18258/47A patent/GB627814A/en not_active Expired
- 1947-07-28 FR FR950228D patent/FR950228A/fr not_active Expired
- 1947-12-23 CH CH283456D patent/CH283456A/fr unknown
- 1947-12-23 CH CH285169D patent/CH285169A/fr unknown
-
1948
- 1948-02-16 FR FR980372D patent/FR980372A/fr not_active Expired
- 1948-04-06 ES ES0183158A patent/ES183158A1/es not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB519208A (en) * | 1938-09-17 | 1940-03-19 | John David Kendall | Improvements in or relating to colour photography |
| US2220123A (en) * | 1938-10-01 | 1940-11-05 | Bela Gaspar | Color photographic process |
| US2310943A (en) * | 1938-10-05 | 1943-02-16 | Du Pont | Polyvinyl acetals |
| US2189817A (en) * | 1939-03-13 | 1940-02-13 | Du Pont Film Mfg Corp | Color-forming photographic composition, element, and process |
| US2313586A (en) * | 1939-08-24 | 1943-03-09 | Eastman Kodak Co | Hydroxynaphthoic acid amide coupler |
| US2357394A (en) * | 1940-07-12 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2324832A (en) * | 1940-07-16 | 1943-07-20 | Gen Aniline & Film Corp | Photographic emulsion |
| US2455169A (en) * | 1944-05-03 | 1948-11-30 | Eastman Kodak Co | Colored couplers |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2706684A (en) * | 1952-11-28 | 1955-04-19 | Eastman Kodak Co | 1-hydroxy-2-naphthamide colored couplers |
| US3077402A (en) * | 1954-12-06 | 1963-02-12 | Polaroid Corp | Photographic color processes, products, and compositions |
| US3034892A (en) * | 1958-10-27 | 1962-05-15 | Eastman Kodak Co | Magenta-colored cyan-forming couplers |
| US3227550A (en) * | 1962-09-07 | 1966-01-04 | Eastman Kodak Co | Photographic color reproduction process and element |
| US3459552A (en) * | 1965-02-03 | 1969-08-05 | Fuji Photo Film Co Ltd | Silver halide emulsions containing magenta-colored cyan couplers |
| US3658545A (en) * | 1968-12-20 | 1972-04-25 | Konishiroku Photo Ind | Light-sensitive silver halide color photographic material containing cyan couplers |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0204530A2 (en) | 1985-05-31 | 1986-12-10 | Konica Corporation | Method for forming direct positive color image |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0228914A2 (en) | 1985-12-28 | 1987-07-15 | Konica Corporation | Method of processing lightsensitive silver halide color photographic material |
| JPH0677141B2 (ja) | 1986-01-20 | 1994-09-28 | コニカ株式会社 | ハロゲン化銀カラ−写真感光材料 |
| JPH0715562B2 (ja) | 1986-01-20 | 1995-02-22 | コニカ株式会社 | ハロゲン化銀カラ−感光材料 |
| 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 |
| US5178993A (en) * | 1990-03-01 | 1993-01-12 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic material |
| US5286287A (en) * | 1990-10-11 | 1994-02-15 | Toyo Ink Manufacturing Co., Ltd. | Monoazo lake pigment suitable for use in printing ink and process for the production thereof |
| US5256772A (en) * | 1990-11-14 | 1993-10-26 | Toyo Ink Manufacturing Co., Ltd. | Monoazo lake pigment and uses thereof |
| EP0711804A2 (de) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Kryptolichtschutzmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| ES183158A1 (es) | 1948-06-01 |
| BE480525A (en)) | |
| CH285169A (fr) | 1952-08-31 |
| FR950288A (fr) | 1949-09-22 |
| FR980372A (fr) | 1951-05-11 |
| CH283456A (fr) | 1952-06-15 |
| FR950228A (fr) | 1949-09-21 |
| GB627814A (en) | 1949-08-16 |
| BE476362A (en)) |
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