US3226230A - Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers - Google Patents
Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers Download PDFInfo
- Publication number
- US3226230A US3226230A US65883A US6588360A US3226230A US 3226230 A US3226230 A US 3226230A US 65883 A US65883 A US 65883A US 6588360 A US6588360 A US 6588360A US 3226230 A US3226230 A US 3226230A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- color
- light
- layer
- naphthamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000839 emulsion Substances 0.000 title claims description 29
- ZTXWIKHKNGFJAX-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=CC=C21 ZTXWIKHKNGFJAX-UHFFFAOYSA-N 0.000 title 1
- 230000001617 migratory effect Effects 0.000 title 1
- -1 AMINO Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- MRBHUTYSDDTIIF-UHFFFAOYSA-N 1-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 MRBHUTYSDDTIIF-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000009102 absorption Effects 0.000 description 3
- 150000003931 anilides Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- YUJYEGDMJZHLMY-UHFFFAOYSA-N 2-chloro-1,3,2-benzodioxaphosphole Chemical compound C1=CC=C2OP(Cl)OC2=C1 YUJYEGDMJZHLMY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910021538 borax Inorganic materials 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- KRAWOYVPVQRUAE-UHFFFAOYSA-N 2-(4-aminoanilino)acetic acid Chemical compound NC1=CC=C(NCC(O)=O)C=C1 KRAWOYVPVQRUAE-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical class CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- CECSFOPGNSJNAM-UHFFFAOYSA-N 4-chloro-1-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)N)=CC(Cl)=C21 CECSFOPGNSJNAM-UHFFFAOYSA-N 0.000 description 1
- XTBFKMDOQMQYPP-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CCN(CC)C1=CC=C(N)C=C1 XTBFKMDOQMQYPP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- 230000002180 anti-stress Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical group OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-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
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- 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 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers
Definitions
- a photographic color image by developing a reducible silver salt image in the presence of a color coupler, i.e. a compound which during development couples with the oxidation product of the developing agent and forms a dyestufl on the area where the silver salt is reduced.
- a color coupler i.e. a compound which during development couples with the oxidation product of the developing agent and forms a dyestufl on the area where the silver salt is reduced.
- the modern methods of color photography are based upon the subtractive color principle according to which differently sensitized silver halide emulsion layers are superposed, each of them containing a color coupler which produces the subtractive yellow-, cyanand magenta-dyestufl images by development in a solution containing a primary aromatic amine.
- the new color couplers can be prepared by condensation of a l-hydroxy-Z-naphthoic acid or a derivative thereof with the aromatic amine desired.
- a sulfonic acid group it is advantageous to bring into the naphthol resp. anilide group before the condensation a sulfofluoride group which after condensation is saponified to the corresponding sulfonic acid, e.g. by application of the method described in Belgian patent specifications 584,152 and 590,934.
- the color couplers must be incorporated into a photographic silver halide emulsion which in its turn is incorporated into a material having one or more layers.
- the color couplers can be incorporated into said emulsions by means of the usual colloids such as gelatin, polyvinyl alcohol, collodium or other natural or synthetic colloids such as e.g. those prepared according to the Belgian patent specification 568,153.
- the silver halide emulsions can be applied to a support consisting of paper, glass, nitrocellulose, cellulose esters such as cellulose triacetate, polyester, polystyrene or an other natural or synthetic resin.
- This multilayer material is usually composed of the following layers: a support, a red-sensitive emulsion layer having a color coupler for cyan, a green light-sensitive emulsion layer with color coupler for magenta and a blue-light sensitive emulsion layer having a color coupler for yellow. Between the blue-light sensitive and the green-light-sensitive emulsion layer, there is a yellow filter layer which in most cases consists of colloidal silver.
- the new color couplers into the light-sensitive silver halide emulsion layer itself but they can also be incorporated into an adjacent non-light-sensitive colloid layer or into a non-lightsensitive layer which is separated from the light-sensitive emulsion layer by a water-permeable colloid layer.
- aromatic amino-compounds can be used as developers for such material: mono-, diand triaminoaryl compounds, more especially N,N-dialkyl-p-phenylene diamine and its derivatives such as N,N-dialkyl-N'- sulphomethylor carboxymethyl p-phenylenediamine.
- mono-amino-developer aminophenols and aminocresols, or their halogen derivatives and also the aminonaphthols are considered.
- Example 1 10 parts of N-[(2-cetylmercapto-5-sulfo)phenyl]-1- hydroXy-4-bromo-2-naphthoic acid amide sodium salt are wetted with 40 parts of ethanol. The whole is dissolved by adding 20 parts of water and by heating at 40 C. This solution is diluted with Water up to 200 parts till obtaining a 5% solution. 200 parts of this color coupler solution and 260 parts of Water are added to 500 parts of silver bromo-iodide gelatin emulsion (2% iodide). After adding the usual additives such as hardening agents and wetting agents the emulsion obtained is coated onto a photographic support. After drying, the photographic material is exposed and treated with a developing solution of the following composition:
- N,N-diethyl-p-phenylenediamine hydrochloride 2.75 Sodium sulphite 2 Potassium carbonate 75 Potassium bromide 0.5 Hydroxylamine hydrochloride 1.2 Sodium hexametaphosphate 1.0
- This material is rinsed for 30 seconds and fixed in a fixing bath of the following composition:
- Example 2 10 parts of N (2-cetylmercapto-5-sulfophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide sodium salt are wetted with 20 parts of ethanol dissolved into 180 parts of water. Now the color coupler solution is incorporated into the emulsion according to Example 1. The material is exposed and treated in the same way as described in Example 1. A cyan image is obtained which shows loW side-absorptions.
- Example 3 10 parts of N-(o-cetylmercaptophenyl)-1-hydroxy-4- chloro-2-naphthoic acid amide are wetted with 30 parts of ethanol and dissolved in 25 parts of 1 N sodium hydroxide and parts of water. The color coupler solution is brought into the emulsion as described in Example 1. The emulsion is neutralized by 7.5 parts of acetic acid N/2 per 100 parts of color coupler solution.
- Example 1 After exposure, the material is treated according to Example 1 whereby in the color developing bath 4-amino-N-ethyl- N (,8 methylsulfonamidoethyl)-rn-toluidine sesquisulphate monohydrate is substituted for N,N-diethyl-p-phen.-
- Example 5 200 cm. of a solution 5% of N-(4-cetylmercapto-5- sulfophenyl) -1-hydroxy-4-sulfo-2-naphthoic acid disodium salt (10 g. of color coupler dissolved in cm. of ethanol and cm. of sodium hydroxide N/ 2 diluted with water to 200 cm?) are added to 500 cm. of a red-sensitized silver bromo-iodide emulsion (2% iodide). After acidification with acidic acid N/ 2 to a pH 6.5, the total volume of the emulsion is brought to 1 1.
- This emulsion is coated onto a support which alreay is coated with an anti'nalation layer.
- a gelatin intermediate layer on which is coated a greenlight-sensitive emulsion layer with color coupler for magenta and covered with a yellow filter layer consisting of a thin gelatin layer containing colloidal silver.
- a blue-light-sensitive emulsion layer with a color coupler for yellow On this filter layer is then coated a blue-light-sensitive emulsion layer with a color coupler for yellow.
- This layer is coated with an antistress layer.
- the photographic material obtained is dried, exposed and color developed according to Example 1. In this way an image with a subtractive color reproduction of the original is obtained which has an increased transparency in the green.
- methyl Cellosolve is a registered trademark for (ethylene glycol monomethyl ether) manufactured by Union Carbide and Carbon, New York, and is used in the foregoing specification.
- X is selected from the group consisting of a bromine atom and chlorine atom
- Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group
- R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufficient to render said color coupler resistant to difiusion.
- Light-sensitive element comprising a red light-sensitive silver halide emulsion layer and a l-hydroxy-Z-naththoic acid anilide color coupler for cyan for said layer, said color coupler being selected from the group consisting of compounds having the formulae:
- X is selected from the group consisting of a bromine atom and a chlorine atom
- Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group
- R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufiicient to render said color coupler resistant to diffusion.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE2039565 | 1960-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3226230A true US3226230A (en) | 1965-12-28 |
Family
ID=3864718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US65883A Expired - Lifetime US3226230A (en) | 1960-02-12 | 1960-10-31 | Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3226230A (US20080005853A1-20080110-C00024.png) |
| BE (1) | BE587525A (US20080005853A1-20080110-C00024.png) |
| GB (1) | GB975928A (US20080005853A1-20080110-C00024.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542552A (en) * | 1966-12-28 | 1970-11-24 | Fuji Photo Film Co Ltd | Color developer for color photography |
| US3622337A (en) * | 1968-08-02 | 1971-11-23 | Gaf Corp | Cyan color formers for color photography |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH227990A (de) * | 1940-07-17 | 1943-07-31 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von photographischen Farbenbildern. |
| US2474293A (en) * | 1947-09-10 | 1949-06-28 | Eastman Kodak Co | 1-naphthol-2-carboxylic acid amide couplers for color photography |
| US2979405A (en) * | 1956-06-22 | 1961-04-11 | Gevaert Photo Prod Nv | Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler |
| US2993791A (en) * | 1957-10-31 | 1961-07-25 | Gen Aniline & Film Corp | Color couplers containing long chain alkylaminoisophthalicester groups |
| US3005709A (en) * | 1958-01-13 | 1961-10-24 | Gen Aniline & Film Corp | Photographic couplers containing acylamino groups |
| US3006759A (en) * | 1959-08-03 | 1961-10-31 | Eastman Kodak Co | Two-equivalent magenta-forming couplers for color photography |
| US3013879A (en) * | 1956-12-31 | 1961-12-19 | Gevaert Photo Prod Nv | Production of color photographic images |
-
0
- BE BE587525D patent/BE587525A/xx unknown
-
1960
- 1960-10-31 US US65883A patent/US3226230A/en not_active Expired - Lifetime
-
1961
- 1961-01-31 GB GB3602/61A patent/GB975928A/en not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH227990A (de) * | 1940-07-17 | 1943-07-31 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von photographischen Farbenbildern. |
| US2474293A (en) * | 1947-09-10 | 1949-06-28 | Eastman Kodak Co | 1-naphthol-2-carboxylic acid amide couplers for color photography |
| US2979405A (en) * | 1956-06-22 | 1961-04-11 | Gevaert Photo Prod Nv | Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler |
| US3013879A (en) * | 1956-12-31 | 1961-12-19 | Gevaert Photo Prod Nv | Production of color photographic images |
| US2993791A (en) * | 1957-10-31 | 1961-07-25 | Gen Aniline & Film Corp | Color couplers containing long chain alkylaminoisophthalicester groups |
| US3005709A (en) * | 1958-01-13 | 1961-10-24 | Gen Aniline & Film Corp | Photographic couplers containing acylamino groups |
| US3006759A (en) * | 1959-08-03 | 1961-10-31 | Eastman Kodak Co | Two-equivalent magenta-forming couplers for color photography |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542552A (en) * | 1966-12-28 | 1970-11-24 | Fuji Photo Film Co Ltd | Color developer for color photography |
| US3622337A (en) * | 1968-08-02 | 1971-11-23 | Gaf Corp | Cyan color formers for color photography |
Also Published As
| Publication number | Publication date |
|---|---|
| GB975928A (en) | 1964-11-25 |
| BE587525A (US20080005853A1-20080110-C00024.png) |
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