US3328419A - Colour couplers and their production and use in colour photography - Google Patents

Colour couplers and their production and use in colour photography Download PDF

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Publication number
US3328419A
US3328419A US375308A US37530864A US3328419A US 3328419 A US3328419 A US 3328419A US 375308 A US375308 A US 375308A US 37530864 A US37530864 A US 37530864A US 3328419 A US3328419 A US 3328419A
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parts
colour
sulphonamide
phenyl
nitrogen
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Anderson Brian
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Ilford Imaging UK Ltd
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Ilford Ltd
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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
    • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3

Definitions

  • the colour coupler is incorporated in the photographic emulsion layer in which the image is ultimately to be formed, it is important that it should be non-diffusing in such layer, i.e. that it should neither diffuse away during the processing steps nor migrate from its layer to any adjacent layer.
  • Many attempts have been made to achieve this characteristic of non-diffusibility, i.e. to make the colour coupler substantive to the medium, usually gelatin, of the photographic emulsion.
  • the methods which have been employed consist generally in the use of colour couplers containing groups of substantial molecular size, e.g. long chain alkyl groups, and also solubilising groups.
  • Such colour couplers are often manufactured by a synthesis in which the group conferring non-difiusion and the solubilising group are introduced at separate stages and the colour couplers are often difficult to isolate and purify. It is one object of the present invention to provide a new class of colour couplers which are non-diffusing in photographic emulsion layers, and which may be manufactured by a simple synthetic process in which two solubilising groups and a group conferring non-diffusion are introduced simultaneously, and further the carboxylic acid group may be obtained in a protected form if so desired.
  • COOH I where the COOH group is ortho to the carbonylamino group
  • colour couplers of the foregoing general Formulas I and II are prepared by condensing a compound of the general Formula III o 0 III with a colour coupler of the general formula B-NH where B has the meaning assigned to it above.
  • a compound of the general Formula II is obtained if the ring structure of the compound of Formula III is retained; otherwise, if the ring opens, a product of Formula I is obtained.
  • the colour couplers containing an amino group which may be used in the process of the invention are for example:
  • Phenols and l-naphthols which contain an amino group, for example 4-chloro-5-1nethyl-2-aminophenol or the aminophenols described in British patent specification Nos. 797,141; 754,306; l-a-mino-S-naphthol, N(B-aminoethyl)-l-hydrOXy-Z-naphthamide or similar N-substituted naphthamides containing an amino group, as described in British patent specification No. 902,266 which may also be substituted in the 4-position, as described in British patent specification No. 757,3 68 and which give cyan dyestuffs on colour development with substituted p-phenylene diamines.
  • an amino group for example 4-chloro-5-1nethyl-2-aminophenol or the aminophenols described in British patent specification Nos. 797,141; 754,306; l-a-mino-S-naphthol,
  • the new colour couplers of the invention may be used in the developing solution or they may be included in a light-sensitive layer or in a non-light-sensitive layer adjacent to a sensitive layer or separated therefrom by a waterpermeable colloid layer.
  • the multilayer colour photographic material may be a natural order material in which the images are to be formed in colours complementary to those of the original object or one in which an unnatural order is used, for example one in which in the top layer there is formed a yellow image of the blue parts of the object, in one of the two layers there is formed a cyan image of the green parts of the object and in the other a magenta image of the red parts of the object.
  • the new colour coupler-s may be incorporated in the photographic emulsion layers by taking them up in dilute alkali, e.g. dilute sodium hydroxide, and adding the resulting solution to the emulsion.
  • dilute alkali e.g. dilute sodium hydroxide
  • the alkali may cause the ring structure to break down yielding a product of Formula 1.
  • the compounds may be dispersed, in a non-slovent medium, and the dispersion added to a photographic emulsion. Since in this case alkali is not used the products ofFormula II remain with their ring structure intact, though they are possibly broken down by the eflect of treatment of the emulsions with alkaline developers. 7
  • EXAMPLE 1 Z-carboxy-N- (1 -phenyl-pyraz0l0ny l-3 -benzam'ide- 4-N'- (4-d0decy lphenyl sulphonamide chloride obtained is removed by filtration. The solution is then evaporated to dryness in vacuo and the residue dissolved in 200 parts of water by the addition of 2 N sodium hydroxide solution. After filtering, the solution obtained is acidified with 2 N hydrochloric acid to precipitate the product which is collected by L-filtration and dried. The 7.1 parts of phthalic acid-4-N-(4-dodecylphenyl) sulphonamide are obtained as a colourless solid melting at 164-165 C.
  • a photographic layer containing the colour coupler may be obtained in the following manner:
  • a mixture of 1.54 parts of the col-our coupler and 12 parts of n-propyl alcohol is warmed to dissolve and 2.35 parts of 2 N potassium hydroxide then added.
  • the solution so obtained is diluted to 30 parts with distilled Water and added to 500 parts of a green sensitised gelatino silver halide emulsion containing silver halide equivalent to 2.5 parts of silver and 3.5% gelatin.
  • the emulsion is then coated on film base and the coated layer dried.
  • phthalic anhydride-4-N-(4-dodecylphenyl) sulphonamide used in the above example may be prepared as follows:
  • a mixture of 30 parts of phthalic acid-4-N-(4-dodecylphenyl)-sulphonamide and 300 parts of acetyl chloride is heated under reflux for 1 hour then evaporated to dryness in vacuo.
  • the solid residue is recrystallised from 400 parts of 60-80 grade petroleum ether.
  • the 12.5 parts of phthalic anhydride-4-N-(4-dodecylphenyl) sulphonamide are obtained as a colourless crystalline solid melting at 83 C.
  • the compound is found to contain 66.3% of carbon, 7.0% of hydrogen, 3.1% of nitrogen and 6.8% of sulphur. (C H 'NO S requires 66.3% of carbon, 7.0% of hydrogen, 3.0% of nitrogen and 6.8% of sulphur.)
  • the phthalic acid-4-N-(4-dodecylphenyl) sulphonamide itself may be prepared as follows:
  • a mixture of 5.3 parts of phthalic acid-4-sulphon.ch1o-; ride, 10.44 parts of p-dodecylaniline and '100 parts of ethyl acetate is heated under reflux for 12 hours, cooled to 20 C. and the precipitate of p-dodecylaniline hydro- COOH
  • a mixture of 7.85 parts of 4-methoxy-3-(4-methoxybenzoylacetamido)aniline, 11.75 parts of phthalie anhydride 4-N-(4-dodecylphenyl)sulphonamide and parts of ethyl acetate is heated at 50 C. for 1 hour, 500 parts of 60-80 grade petroleum ether are then added and the precipitate obtained filtered off, dried and recrystal-, lised from 1 20 parts of methanol.
  • a photographic layer containing the colour coupler may be obtained in the following manner:
  • a mixture of 3.8 parts of the colour coupler and 20 parts of n-propyl alcohol is warmed to dissolve and 3.5 parts of 2 N potassium hydroxide solution then added.
  • the solution so obtained is diluted to 70 parts with distilled water and added to 500 parts of a blue sensitised gelatino silver halide emulsion containing silver halide equivalent to 7.0 parts of silver and 4% gelatin.
  • the emulsion is then coated on film base and the coated layer dried.
  • EXAMPLE 5 EXAMPLE 3 5 Z-carboxy N 4-(3:5 dicarbomethoxyphenylaminocar- Z-carbOxy-N-[B(I-hydroxy-Z-naphthamido)ethyl]benzbonyl)acetyl]phenylb enzamide 4 N (4 dodecylamiae-4-N'-(4-d0decylphenyl)sulphonam ide phenyl)sulphonamide $OOCH3 Q-NHC O CHiC OQNHO (IQ-S OaNHQ-CnHzs (2000113 H006 CONH.CH2OH2NHOC-SO2-NHC:2H25
  • the product is obtained by evaporating the is added to 500 parts of a red sensitised gelatino silver reaction mixture to dryness in vacuo and recrystallising halide emulsion containing silver halide equivalent to 2.0 the residue from methanol.
  • the emulsion is then [4-.(4-methoxybenzoylacetamido) 2:5 diethoxyphenyl] coated on a paper base and the coated layer dried.
  • benzamide-4-N'-(4-dodecylphenyl)sulphonamide are obthe photographic layer so obtained is exposed to red light, tained as a solid melting at 94-96 C.
  • the 4 (4 methoxybenzoylacetamido)-2:S-di-ethoxyaniline used in the above example is prepared as follows EXAMPLE 4 A mixture of 40 parts of 4-(4-methoxybenzoylacet- 2-carb0xy-N-[fi(4-chlar 1 hydroxy 2 naphlhamido) amido)-2:5-di-ethoxy nitrobenzene, 800 parts of ethyl ethyl]benzamide-4-N'-(4 d0decylphenyl)sulphonamide alcohol and Raney nickel catalyst is heated'with hydro- OH V ,7 l
  • decylphenyl)sulphonamide are obtained as a colourless solid melting at 203204 C. and on analysis is found to The (4' y ynlcontain 64.0% of carbon, 6.0% of hydrogen and 5.5 of 75 trobenzene itself maybe prepared as follows:
  • the product is isolated by pouring 0f 4-(4-1'11ethoxybflflzoylacetamidonitl'obenzefle am into an excess of petroleurn'ether.
  • the 19.6 parts of 2- tained as a pale yellow needle crystal melting at 197- carboxy N- ⁇ 3-[(,5-ehlor-4-methyl-2-hydroxyphenyl) 198 C.
  • aminocar-bonyl]phenyl ⁇ benzamide -4-N (4 dodecyl
  • phenyl)sul phonamide are obtained as a solid melting at Z-carboxy-N-[4-(methoxyb enzoylacetam idoy) h l] 2l0213 C.
  • EXAMPLE 8 product is recrystallised from glacial acetic acid.
  • N-(4-methoxybenzoylacetamido)phenylphthalimide-4- 50 The 11.2 parts of N- ⁇ 4-[N-(l-phenyl-S-pyrazolonyl- N'-(4-d0decylphenyl)sulphrmamide 3-)aminoacetyl]phenyl ⁇ phthalimide-4 N (4 dodecyloo CHaO-COCHzCONH- 41 SOENEP-QCHHIS 1
  • a mixture of 9.94 parts of 4-(4-methoxybenzoylacetaphenyl)sulphonamide are obtained as a solid melting at mido)aniline, 16.45 parts of phthalic anhydride-4-N-(4- 6O 228231 C.
  • EXAMPLE 13 2-carboxy-N-[;8(I-hydroxyQ-rtaphthamido) ethyl] benzamide-4-N'n-0ctadecylsulphonamide o oNHomomNHoo-Q-somnmrm crystallised from ethyl acetate.
  • the 7.0 parts of 2- carboxy N [3(1 hydroxy-Z-naphthamido)ethyl]benzamide-4-n-octadecylsulphonamide are obtained as a colourless solid melting at 225-226 C. and on analysis is found to contain 66.1 of carbon, 8.6% of hydrogen and 4.1% of sulphur. (C39H55N3S07 requires 66.1% of carbon, 7.8% of hydrogen and 4.5% of sulphur.)
  • the phthalic anhydride 4-N-n-octadecylsulphonamide used in the above example may be prepared as follows: A mixture of 26.9 parts of n-octadecylamine, 29.2 parts of phthalic acid-4-sulphonyl chloride, 8.2 parts of anhydrous sodium acetate and 400 parts of ethyl acetate is heated under reflux for 12 hours then evaporated down to dryness. To the residue is added 600 parts of acetyl chloride and the mixture heated under reflux for /2 hour. After filtering hot the solution is cooled to crystallise, the product collected by filtration and recrystallised from ethyl acetate.
  • a color coupler which is a compound selected from the group consisting of compounds of the formula:
  • R is a. member selected from the group consist- EXAMPLE 17 ing of alkyl and Ialkyl substituted phenyl, wherein the alkyl radical, and the alkyl substituent contain from 12 2 -arb0xy-N-[Z- ⁇ fi-(4-Chl0r0 1 hydroxy 2 naphthto 18 carbon atoms, and B is the residue of a compound amid0)ethyl ⁇ phenyl]benzamide-4 N (4 dodecyl- BNH which is selected from the group consisting of phenyl)sulph0namide (I) Ho 0 c- SO;NH-C ,H
  • R is phenyl
  • one of X and Y is --NH and the other is H
  • X is NH and Y is anilino or X is H and Y is -NH aminophenylacetylamino, or (Z-methoxy- 5-amino)anilino.
  • B is the residue of a compound BNH which is selected from the group consisting of N-(fi-aminoethyl)-1-hydroxy-2- napthamide, N (B aminoethyl) 4 chloro 1 hydroxy 2 napthamide, 2 (o amino B phenylethyl)- 1 hydroxynaphthamide, 1 (1 hydroxy 2 naphthamide)-6-aminohexane, and 2-(o-amino-fi-phenylethyl)-1-hydroxy-4-chl0ronaphthamide.
  • BNH which is selected from the group consisting of N-(fi-aminoethyl)-1-hydroxy-2- napthamide, N (B aminoethyl) 4 chloro 1 hydroxy 2 napthamide, 2 (o amino B phenylethyl)- 1 hydroxynaphthamide, 1 (1 hydroxy 2 naphthamide)-6-aminohexane, and 2-(o-amino-fi-phen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US375308A 1963-06-17 1964-06-15 Colour couplers and their production and use in colour photography Expired - Lifetime US3328419A (en)

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GB24027/63A GB997500A (en) 1963-06-17 1963-06-17 Improvements in or relating to colour couplers and to their production and use in colour photography

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547944A (en) * 1964-02-20 1970-12-15 Ilford Ltd Colour photography utilizing colour couplers which yield quinone imine or azamethine dye images
US3711286A (en) * 1968-02-07 1973-01-16 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion
US3973968A (en) * 1971-04-26 1976-08-10 Konishiroku Photo Industry Co., Ltd. Photographic acyl acetanilide color couplers with 2,5-dioxo-1-imidazolidinyl coupling off groups
US4106940A (en) * 1974-10-03 1978-08-15 Agfa-Gevaert, A.G. Light-sensitive material containing emulsified substances
US4269936A (en) * 1971-12-28 1981-05-26 Fuji Photo Film Co., Ltd. Process of forming yellow photographic images
US4404274A (en) * 1971-03-20 1983-09-13 Fuji Photo Film Co., Ltd. Photographic light sensitive element containing yellow color coupler and method for forming yellow photographic images
US4835094A (en) * 1986-10-01 1989-05-30 Agfa-Gevaert Aktiengesellschaft Color photographic recording material containing a color coupler of the pyrazoloazole series

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2083216A (en) * 1934-06-20 1937-06-08 Gen Aniline Works Inc Monoazo dyes
US2710803A (en) * 1953-03-26 1955-06-14 Eastman Kodak Co Color couplers containing hydroxyalkyl groups
US2837557A (en) * 1953-04-22 1958-06-03 Union Carbide Corp Esters of n, nu-bis(2-cyanoethyl) carboxamic acids
US2878263A (en) * 1958-02-14 1959-03-17 Ortho Pharma Corp 4-methyl-4-phenyl-5-pyrazolone
US2905694A (en) * 1959-09-22 Certain esters of i
US2933391A (en) * 1956-09-06 1960-04-19 Eastman Kodak Co Photographic emulsions containing 5-pyrazolone coupler compounds
US2983608A (en) * 1958-10-06 1961-05-09 Eastman Kodak Co Yellow-colored magenta-forming couplers
US3034891A (en) * 1958-07-31 1962-05-15 Gen Aniline & Film Corp Procedure for the production of yellow dye images by color development
US3148178A (en) * 1962-11-07 1964-09-08 Eastman Kodak Co Azo compounds containing a dicarboximido radical

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2905694A (en) * 1959-09-22 Certain esters of i
US2083216A (en) * 1934-06-20 1937-06-08 Gen Aniline Works Inc Monoazo dyes
US2710803A (en) * 1953-03-26 1955-06-14 Eastman Kodak Co Color couplers containing hydroxyalkyl groups
US2837557A (en) * 1953-04-22 1958-06-03 Union Carbide Corp Esters of n, nu-bis(2-cyanoethyl) carboxamic acids
US2933391A (en) * 1956-09-06 1960-04-19 Eastman Kodak Co Photographic emulsions containing 5-pyrazolone coupler compounds
US2878263A (en) * 1958-02-14 1959-03-17 Ortho Pharma Corp 4-methyl-4-phenyl-5-pyrazolone
US3034891A (en) * 1958-07-31 1962-05-15 Gen Aniline & Film Corp Procedure for the production of yellow dye images by color development
US2983608A (en) * 1958-10-06 1961-05-09 Eastman Kodak Co Yellow-colored magenta-forming couplers
US3148178A (en) * 1962-11-07 1964-09-08 Eastman Kodak Co Azo compounds containing a dicarboximido radical

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547944A (en) * 1964-02-20 1970-12-15 Ilford Ltd Colour photography utilizing colour couplers which yield quinone imine or azamethine dye images
US3711286A (en) * 1968-02-07 1973-01-16 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion
US4404274A (en) * 1971-03-20 1983-09-13 Fuji Photo Film Co., Ltd. Photographic light sensitive element containing yellow color coupler and method for forming yellow photographic images
US3973968A (en) * 1971-04-26 1976-08-10 Konishiroku Photo Industry Co., Ltd. Photographic acyl acetanilide color couplers with 2,5-dioxo-1-imidazolidinyl coupling off groups
US4269936A (en) * 1971-12-28 1981-05-26 Fuji Photo Film Co., Ltd. Process of forming yellow photographic images
US4106940A (en) * 1974-10-03 1978-08-15 Agfa-Gevaert, A.G. Light-sensitive material containing emulsified substances
US4835094A (en) * 1986-10-01 1989-05-30 Agfa-Gevaert Aktiengesellschaft Color photographic recording material containing a color coupler of the pyrazoloazole series

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DE1493852A1 (de) 1969-05-22
CH445475A (de) 1967-10-31
BE649351A (de) 1964-10-16
GB997500A (en) 1965-07-07
NL6406892A (de) 1964-12-18

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