US3056674A - Color formers for producing yellow dye images by color development - Google Patents
Color formers for producing yellow dye images by color development Download PDFInfo
- Publication number
- US3056674A US3056674A US86281A US8628161A US3056674A US 3056674 A US3056674 A US 3056674A US 86281 A US86281 A US 86281A US 8628161 A US8628161 A US 8628161A US 3056674 A US3056674 A US 3056674A
- Authority
- US
- United States
- Prior art keywords
- color
- coupler
- yellow
- photographic
- formers
- 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
- 238000011161 development Methods 0.000 title description 10
- 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 title description 8
- 239000001043 yellow dye Substances 0.000 title description 8
- -1 SILVER HALIDE Chemical class 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 11
- 229910052709 silver Inorganic materials 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000306 component Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- TWENAWDEQLMDQL-UHFFFAOYSA-N 3-amino-4-tetradecoxybenzoic acid Chemical compound NC=1C=C(C(=O)O)C=CC1OCCCCCCCCCCCCCC TWENAWDEQLMDQL-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HMMPSBABGKHKKX-UHFFFAOYSA-N acetyl 4-cyano-2-ethylbenzoate Chemical compound CCC1=CC(C#N)=CC=C1C(=O)OC(C)=O HMMPSBABGKHKKX-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- IYENIONECPQKLR-UHFFFAOYSA-N 3-amino-4-octoxybenzoic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=C1N IYENIONECPQKLR-UHFFFAOYSA-N 0.000 description 1
- WOQBMUQZUJEXTD-UHFFFAOYSA-N 4-[(3-oxo-3-phenylpropanoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)CC(=O)C1=CC=CC=C1 WOQBMUQZUJEXTD-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 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
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001050 dyes by color Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 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
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/362—Benzoyl-acetanilide couplers
Definitions
- a phenol or phenolic type of compound such as a naphthol.
- pyrazolones are frequently employed, whereas the yellow image is formed from an a-arylacetanilide structure. It is this latter representative of color formers with which the present invention is concerned.
- Yellow color forming components of the type derived from an c-arylacetanilide can be formulistically depicted as follows:
- couplers of this type embody a reactive methylene grouping, i.e., a structure characterized by the presence of a methylene bridge linked to various negative groupings which, in the above formula, are keto functions located on either side of the methylene bridge. It is the methylene portion of the coupler, the hydrogen atoms of which are acidic by virtue of the electron-attracting keto functions, which couples with the oxidized primary aromatic amino developing agent to produce the colored dye images.
- R is a higher alkyl group having from 8 to 20 carbon atoms, the purpose of which is to prevent wandering or difiusion of the color forming compounds throughout the emulsion layer with concomitant color degradation.
- Suitable alkyl moieties for this purpose include alkyl groups such as octyl, nonyl, decyl, undecyl, tetradecyl, octadecyl, eicosyl and the like; M and M which may be alike or different can be hydrogen or a carboxylic acid salt such as an ammonium salt including amine salts, alkali metal salts, i.e., lithium, potassium, sodium, etc.
- the designation of M and M will depend to some extent on the pH of the emulsion in which the coupler is incorporated.
- the coupler may be added in the form of its alkali metal salt to the emulsion which, after the coating operation, may be subjected to conditions of lower pH causing the coupler to be converted to its acid form. It is to be understood, therefore, that the coupler structures as herein described are not limited to any particular salt or free acid form.
- a novel feature of the couplers as described herein for producing yellow dye images on color development is the presence of a carboxylic acid function on the para-position of the benzoyl grouping. That this particular structural modification has heretofore been unknown to the art is indeed not surprising. Normally such structures would be synthesized by reacting a p-carboxylbenzoyl acetic ester with an aniline to form a benzoyl acetanilide. However, because of the unavailability of p-carboxylbenzoyl acetic ester, this reaction is not suited for producing color former structures of the benzoyl acetanilide type wherein the benzoyl grouping contains a carboxylic acid function particularly in the para-position thereof.
- the ethyl-4-cyanobenzoy1 acetate was prepared by reacting 4-cyanobenzoyl chloride with acetoacetic ester in the presence of sodium methylate. Hydrolysis of the resulting ester complex with a mixture of ammonium chlo ride and ammonium hydroxide yielded the ethyl-4-cyanobenzoyl acetate. After one crystallization from alcohol, the purified product melted at 836 C.
- the preparation of benzoylacetic esters as described herein is patterned after the method published by Thorp and Brunskill in J.A.C.S. 37, 1261.
- the 4-cyanobenzoyl chloride-M.P. 73 C.-- was obtained by acylating the free acid with phosphorous pen tachloride utilizing the method of Scholl and Neuberger M, 33, 517.
- the 4-cyanobenzoic acid was produced by the diazotization of p-aminobenzoic acid followed by treating the resulting diazonium salt with cuprous cyanide (Sandmeyer reaction). The preparation was modeled after the method disclosed by Valby and Lucas in J.A.C.S., 51, 2719 (1929).
- this yellow coupler was patterned after the procedure used in the first example except that the 3-amino-4-tetradecoxybenzoic acid of the earlier example was replaced by the corresponding octadecoxy derivative.
- the color couplers contemplated in the instant invention can be incorporated in a photographic light sensitive silver halide emulsion in the manner well known to the art.
- the coupler can be dissolved in an aqueous alkaline solution which is then blended with the silver halide emulsion and the mixture then coated on a suitable photographic support or base.
- the coupler can be dissolved in any suitable alkaline solution capable of forming soluble salts with the carboxylic functions of the coupler.
- aqueous or alcoholic solutions of organic bases including ammonium hydroxide, alkali metals are especially suitable for this purpose.
- Example 1 Typically, one gram of the color former of Example 1 was dissolved in about 20 milliliters of water containing sufficient sodium hydroxide to impart the solution a pH at about 7.5. The solution was combined with a silver bromide emulsion and the mixture coated on a suitable base such as triacetate filmbase. Upon exposure and development in a color developer containing as the active principal N-ethyl-N-hydroxyethyl-p-aminoaniline there was obtained a brilliant yellow dye image having an absorption maximum at 428 mu.
- M and M are each selected from the class consisting of hydrogen and ammonium group and the alkali metals and R is a higher alkyl group of from 8 to 20 carbon atoms.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE613367D BE613367A (en(2012)) | 1961-02-01 | ||
| US86281A US3056674A (en) | 1961-02-01 | 1961-02-01 | Color formers for producing yellow dye images by color development |
| GB2851/62A GB934017A (en) | 1961-02-01 | 1962-01-25 | Color formers for producing yellow dye images by color development |
| FR886375A FR1318028A (fr) | 1961-02-01 | 1962-01-30 | Formateurs de colorants pour la production d'images de colorant jaune par développement chromogène |
| DEG34149A DE1157483B (de) | 1961-02-01 | 1962-01-30 | Verfahren zur Herstellung gelber Farbbilder mit Hilfe der farbgebenden Entwicklung und lichtempfindliche Silberhalogenidemulsion hierfuer |
| CH124062A CH424477A (de) | 1961-02-01 | 1962-02-01 | Photographische Halogensilberemulsionsschicht |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86281A US3056674A (en) | 1961-02-01 | 1961-02-01 | Color formers for producing yellow dye images by color development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3056674A true US3056674A (en) | 1962-10-02 |
Family
ID=22197510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US86281A Expired - Lifetime US3056674A (en) | 1961-02-01 | 1961-02-01 | Color formers for producing yellow dye images by color development |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3056674A (en(2012)) |
| BE (1) | BE613367A (en(2012)) |
| CH (1) | CH424477A (en(2012)) |
| DE (1) | DE1157483B (en(2012)) |
| GB (1) | GB934017A (en(2012)) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3335011A (en) * | 1962-03-23 | 1967-08-08 | Pavelle Corp | Production of stabilized dispersions of color couplers for photographic materials |
| US3341331A (en) * | 1964-03-23 | 1967-09-12 | Fuji Photo Film Co Ltd | Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers |
| US3393041A (en) * | 1963-07-09 | 1968-07-16 | Gevaert Photo Prod Nv | Multilayer silver halide elements containing thiazole color couplers for yellow |
| US3393040A (en) * | 1963-07-09 | 1968-07-16 | Gevaert Photo Prod Nv | Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers |
| US3421896A (en) * | 1967-08-03 | 1969-01-14 | Gen Aniline & Film Corp | Prevention of silver occulsion in color photography |
| US4842979A (en) * | 1984-12-27 | 1989-06-27 | Fuji Photo Film Co., Ltd. | Black color heat-sensitive diazo microcapsule recording material with benzoylacetic amide coupler |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1246405B (de) * | 1964-03-23 | 1967-08-03 | Fuji Photo Film Co Ltd | Farbfotografisches Material mit einem Farbkuppler fuer Gelb |
| DE102013220908B4 (de) * | 2013-10-15 | 2015-09-24 | Continental Automotive Gmbh | Sensorelement |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2425503A (en) * | 1944-05-20 | 1947-08-12 | Gen Aniline & Film Corp | Nondiffusing couplers for color photography |
| US2694008A (en) * | 1948-10-22 | 1954-11-09 | Agfa Ag Fur Photofabrikation | Process for the production of colored masks in photographic color material |
| CH334344A (de) * | 1954-03-15 | 1958-11-30 | Agfa Ag | Verfahren zur Herstellung farbiger Bilder mittels farbgebender Entwicklung |
| US2875057A (en) * | 1954-12-20 | 1959-02-24 | Eastman Kodak Co | Benzoylacet-o-alkoxyanilide couplers for color photography |
-
0
- BE BE613367D patent/BE613367A/xx unknown
-
1961
- 1961-02-01 US US86281A patent/US3056674A/en not_active Expired - Lifetime
-
1962
- 1962-01-25 GB GB2851/62A patent/GB934017A/en not_active Expired
- 1962-01-30 DE DEG34149A patent/DE1157483B/de active Pending
- 1962-02-01 CH CH124062A patent/CH424477A/de unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2425503A (en) * | 1944-05-20 | 1947-08-12 | Gen Aniline & Film Corp | Nondiffusing couplers for color photography |
| US2694008A (en) * | 1948-10-22 | 1954-11-09 | Agfa Ag Fur Photofabrikation | Process for the production of colored masks in photographic color material |
| CH334344A (de) * | 1954-03-15 | 1958-11-30 | Agfa Ag | Verfahren zur Herstellung farbiger Bilder mittels farbgebender Entwicklung |
| US2875057A (en) * | 1954-12-20 | 1959-02-24 | Eastman Kodak Co | Benzoylacet-o-alkoxyanilide couplers for color photography |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3335011A (en) * | 1962-03-23 | 1967-08-08 | Pavelle Corp | Production of stabilized dispersions of color couplers for photographic materials |
| US3393041A (en) * | 1963-07-09 | 1968-07-16 | Gevaert Photo Prod Nv | Multilayer silver halide elements containing thiazole color couplers for yellow |
| US3393040A (en) * | 1963-07-09 | 1968-07-16 | Gevaert Photo Prod Nv | Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers |
| US3341331A (en) * | 1964-03-23 | 1967-09-12 | Fuji Photo Film Co Ltd | Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers |
| US3421896A (en) * | 1967-08-03 | 1969-01-14 | Gen Aniline & Film Corp | Prevention of silver occulsion in color photography |
| US4842979A (en) * | 1984-12-27 | 1989-06-27 | Fuji Photo Film Co., Ltd. | Black color heat-sensitive diazo microcapsule recording material with benzoylacetic amide coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| BE613367A (en(2012)) | |
| GB934017A (en) | 1963-08-14 |
| CH424477A (de) | 1966-11-15 |
| DE1157483B (de) | 1963-11-14 |
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