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

• This invention relates to photographic emulsions containing coupler compounds for color photography and processes of color photography utilizing coupler compounds for the formation of photographic images.
• our invention relates to couplercompounds for forming yellow dye images in color photography.
• the methylene group of the couplers is substituted with a chlorine atom with the result that the number of mols of silver halide required for the production of one mol of dye from the coupler is reduced from A to 2.
• the apparent advantage is that such couplers require less silver halide to produce a given amount of dye.
• the coupler compounds of our invention have the following general formula: 0
• o-Methoxybenzoylacet-4-nitroanilide is prepared as follows:
• o-Methoxybenzoylacet-4-aminoanilide is prepared as follows:
• the pale yellow solution is chilled to and the precipitate filtered, washed well with 1 l. of cold 3% hydrochloric acid, and dried. 57-582 g. (89-91%) of a pale yellow hydrochloride is obtained. This is mixed intimately with an equal weight of anhydrous sodium acetate and poured with vigorous stirring into 1 l. of ethyl alcohol. (Crystals can be obtained at this point M. P. 103-105 65% yield). After stirring minutes, the reaction mixture is diluted with 1 l. of water, stirred an additional five minutes, and chilled to 5. The precipitate is filtered, washed with 1 l. of cold 50% alcohol, and dried. The yield is 47 g. (83%) of tan crystals which melt at 90-92. A 90% recovery of material melting at 100-102 can be obtained by dissolving the material in 10 parts of ethyl alcohol and diluting with 5 parts of water.
• the desired product I was prepared as follows:
• the desired product II is prepared as follows:
• Amy1phenoxy-n-butyryl chloride is prepared as follows:
• the acid (25 g.) is refluxed one hour in five parts of thionyl chloride.
• the excess thionyl chloride is removed in vacuo and when the viscous residue reaches constant weight the acid chloride is ready for use.
• the yield is ca. 25% based on diamylphenol not recovered.
• reaction mixture becomes murky immediately and is stirred for three hours at room temperature. With goodstirring the reaction mixture is drowned in 300 ml. of
• the desired product III is prepared as follows:
• This coupler compound is outstanding among the other couplers contemplated by our invention because the three terminal alkyl groups apparently enhance its solubility in coupler solvents used for dispersing the coupler in gelatino-silver halide emulsions.
• EXAMPLE IV The precipiof snow white solid which EXAMPLE V oi-(o-Methoxybehzoyl) cL-chlor -S-[u -(2,4 di tent-amylphenoxy)-n-butyramid0]acetanilide V eon.
• llrnoooncnzom is prepared by a procedure similar to Example III with the substitution of o-methoxy-benzoylacet-3-aminoanilide for o-methoxy-benzoylacet-4-aminoanilide as follows:
• a (o Methoxybenzoyl)-4- ⁇ [2 (2,4-di-tent.'-amylphenoxy) -5 3 5 -dicarbomethoxyp henylcarbamyl )phenylcarbamyl]methoxy ⁇ -acetanilide is prepared by first reacting 4-(2,4-di-tert.-amylphenoxy) 3 nitrobenzoyl chloride with 3,5-dicarbomethoxy aniline; reducing the nitro group of the product followed by reaction of the resultant amino group with 4-nitrophenoxyacetyl chloride. The nitro group of this product is then reduced and the product condensed at the resultant amino group with ethyl-omethoxybenzoyl acetate.
• the desired product IV is obtained as follows:
• the desired product V is obtained as follows;
• Coupler iV has the unusual property that the spectral absorption of theazomethine dyes made therefrom by color development, are particularly sharp, that is, the absorption in the blue region of the spectrum is confined to a relatively narrow range of wavelengths which is an effect long sought in dyes for color photography.
• the etiect is due, at least in part, to the alkoxy group in the p-position of acetanilide nucleus of the coupler.
• This coupler is of particular value in those cases where it is desirable to incorporate a coupler into an emulsion by use of alkali rather than a coupler solvent. Accordingly, the ester groups of the above coupler are first hydrolyzed in alcoholic alkali in a well known manner, then the coupler is incorporated into an emulsion as the alkali metal salt.
• All of the couplers of the invention may be incorporated into emulsion layers by the method of Fischer U. S.
• Patent 1,055,155 or by means of coupler solvents by the methods of Mannes et al. U. S. Patent 2,304,940, granted December 15, 1942, and .lelley and Vittum U. S. Patent 2,322,027, granted June 15, 1943.
• the couplers of the invention are primarily useful in multilayer color films and for that purpose the couplers are particularly efficacious since they show relatively little diffusion in gelatin emulsion layers especially when the substituent in the p-position of the acetanilide nucleus is sizeable.
• any color-forming developer containing a primary amino group may be used.
• compounds are usually used in the salt form, such as the hydrochloride or the sulfate which are more stable than the amines themselves.
• the suitable compounds are diethyl-p-phenylenediamine hydrochloride, monomethyl-pphenylenediamine hydrochloride, dimethyl-p-phenylenediamine hydrochloride, and Z-amino-5-diethylaminotoluene hydrochloride.
• the p-amino phenols and their substitutionproducts may also be used where the amino group is unsubstituted. All of these developers have an unsubstituted amino group which enables the oxidation products of the developer to couple with the color-forming compounds to form a dye image.
• Our development process may be employed for the pro- These mixture of silver halide and the coupler compound diduction of colored photographic images in layers of gelatin or other water-permeable colloidal carriers, such as albumin, collodion organic esters of cellulose, or synthetic resins.
• the carrier may be supported by a transparent medium such as glass, a cellulose ester or synthetic resin or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
• the emulsion may be coated as a single layer on the supoprt or as one of a number of superposed layers on one or both sidesof'the support.
• the superposed layers may bedifferentially sensitized as is conventional in color photography.
• a photographic silver halide emulsion comprising a mixture of silver halide and a coupler compound of the class consisting of 4- ct-Z-methoxybenzoyl-a-chloroacetamido) -3"-(4-tert.
• amylphenoxy) benzanilide 4 (a 2-methoxybenzoyl-a-chloroacetamido)-2", 4"-ditert. amylphenoxyacetanilide a 0 Methoxybenzoyl a-chloro-4-[a-(lA-di-terh-amylphenoxy -n-butyramido acetanilide Dimethyl 5 ⁇ 4-(2,4-di-tert.-amylphenoxy) -3- ⁇ a- [4-( 01-0- anisoyl -u.- chloroacetamido) phenoxy] acetamido ⁇ -benzamido ⁇ isophthalate a (o Methoxybenzoyl)a-chloro-3-[a-(ZA-di-tert.
• a photographic silver halide emulsion comprising a mixture of silver halide and the coupler compound Ot-O- methoxybenzoyl on chloro 4 [a-(2,4-di-tert.-amylphenoxy -n-butyramido] -acetanilide.
• a photographic silver halide emulsion comprising a methyl 5- ⁇ 4- 2,4-di-tert.-amylphenoxy) -3- ⁇ cc- [4 a-o-anisoyl a chloroacetamido) phenoxy]acetarnido ⁇ benzamido ⁇ isophthalate.
• a photographic silver halide emulsion comprising a mixture of silver halide and the coupler compound a-(omethoxybenzoyD-a chloro 3-[a-(2,4-di-tert.-amylphenoxy -n-butyramido] -acetanilide.
• a method of producing a colored photographic image in a silver halide emulsion layer which comprises exposing said layer and developing it with a primary aromatic amino silver halide developing agent in the presence of a coupler compound designated in claim 1.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (6)

Citations (2)

• 0
  • BE BE521004D patent/BE521004A/xx unknown
• 1952
  • 1952-06-26 US US295806A patent/US2728658A/en not_active Expired - Lifetime
• 1953
  • 1953-06-25 FR FR1098025D patent/FR1098025A/fr not_active Expired
  • 1953-06-26 GB GB17750/53A patent/GB736922A/en not_active Expired

Patent Citations (2)

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