US2728658A - Benzoyl acetanilide couplers for color photography - Google Patents

Benzoyl acetanilide couplers for color photography Download PDF

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Publication number
US2728658A
US2728658A US295806A US29580652A US2728658A US 2728658 A US2728658 A US 2728658A US 295806 A US295806 A US 295806A US 29580652 A US29580652 A US 29580652A US 2728658 A US2728658 A US 2728658A
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US
United States
Prior art keywords
tert
amylphenoxy
mole
coupler
acetanilide
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Expired - Lifetime
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US295806A
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English (en)
Inventor
Fred C Mccrossen
Paul W Vittum
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority to BE521004D priority Critical patent/BE521004A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US295806A priority patent/US2728658A/en
Priority to FR1098025D priority patent/FR1098025A/fr
Priority to GB17750/53A priority patent/GB736922A/en
Application granted granted Critical
Publication of US2728658A publication Critical patent/US2728658A/en
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    • 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)
US295806A 1952-06-26 1952-06-26 Benzoyl acetanilide couplers for color photography Expired - Lifetime US2728658A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE521004D BE521004A (en)) 1952-06-26
US295806A US2728658A (en) 1952-06-26 1952-06-26 Benzoyl acetanilide couplers for color photography
FR1098025D FR1098025A (fr) 1952-06-26 1953-06-25 Nouvelles o-alkoxybenzoylacétanilides et leurs applications en photographie
GB17750/53A GB736922A (en) 1952-06-26 1953-06-26 Improvements in photographic colour couplers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US295806A US2728658A (en) 1952-06-26 1952-06-26 Benzoyl acetanilide couplers for color photography

Publications (1)

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US2728658A true US2728658A (en) 1955-12-27

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BE (1) BE521004A (en))
FR (1) FR1098025A (en))
GB (1) GB736922A (en))

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2868829A (en) * 1955-01-29 1959-01-13 Ilford Ltd Colour photography
US2998314A (en) * 1956-09-18 1961-08-29 Agfa Ag Color photography
US3077403A (en) * 1960-05-31 1963-02-12 Gen Aniline & Film Corp Color former containing bis coupling functions
US3277155A (en) * 1960-08-24 1966-10-04 Eastman Kodak Co Monofluoro-beta-ketoacetanilide couplers for color photography
US4324898A (en) * 1977-04-29 1982-04-13 Ciba Geigy Ag Heterocyclic compounds useful as color photographic material
US5869735A (en) * 1995-10-20 1999-02-09 Bayer Aktiengesellschaft Process for the preparation of alkyl aryl ethers containing carboxyl groups

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2407210A (en) * 1944-04-14 1946-09-03 Eastman Kodak Co Color couplers
FR959910A (en)) * 1944-11-02 1950-04-07

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2407210A (en) * 1944-04-14 1946-09-03 Eastman Kodak Co Color couplers
FR959910A (en)) * 1944-11-02 1950-04-07

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2868829A (en) * 1955-01-29 1959-01-13 Ilford Ltd Colour photography
US2998314A (en) * 1956-09-18 1961-08-29 Agfa Ag Color photography
US3077403A (en) * 1960-05-31 1963-02-12 Gen Aniline & Film Corp Color former containing bis coupling functions
US3277155A (en) * 1960-08-24 1966-10-04 Eastman Kodak Co Monofluoro-beta-ketoacetanilide couplers for color photography
US4324898A (en) * 1977-04-29 1982-04-13 Ciba Geigy Ag Heterocyclic compounds useful as color photographic material
US5869735A (en) * 1995-10-20 1999-02-09 Bayer Aktiengesellschaft Process for the preparation of alkyl aryl ethers containing carboxyl groups

Also Published As

Publication number Publication date
GB736922A (en) 1955-09-14
BE521004A (en))
FR1098025A (fr) 1955-07-15

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