US3383214A - Color photography utilizing color couplers which yield quinone imine or azamethine dye images - Google Patents

Color photography utilizing color couplers which yield quinone imine or azamethine dye images Download PDF

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US3383214A
US3383214A US432898A US43289865A US3383214A US 3383214 A US3383214 A US 3383214A US 432898 A US432898 A US 432898A US 43289865 A US43289865 A US 43289865A US 3383214 A US3383214 A US 3383214A
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color
hydrogen
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carbon
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Anderson Brian
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Ilford Imaging UK Ltd
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Ilford Ltd
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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
    • G03C7/3212—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • 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

Definitions

  • the color couplers are compounds of the formula or the corresponding cyclised compounds, wherein A is a trivalent monocyclic or dicyclic aryl, with the COOH and CONHB groups ortho or peri to each other, X is hydrogen or lower alkyl, Y is OC, CONH or -COCH when X is hydrogen and Y is O S when X is lower alkyl, B is a residue of a compound BNH which will react with the oxidation products of N,N-diethyl .p'phenylene diamine, formed during the development with a silver salt image with that compound, to yield a quinone imine or azamethine dye image and R is a substituent comprising an alkyl group containing at least 12 carbon atoms.
  • This invention relates to color couplers and to their production and use in color photography.
  • the color 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-diifusibility, i.e. to make the color coupler substantive to the medium, usually gelatin, of the photographic emulsion.
  • the methods which have been employed consist generally in the use of color couplers containing groups of substantial molecular size, e.g. long chain alkyl groups, and also solubiiising groups.
  • Such color couplers are often manufactured by a synthesis which involves several stages and the color couplers are usually difiicult to isolate and purify. It is one object of the present invention to provide a new class of color couplers which are non-diffusing in photographic emulsion layers, and which may be manufactured by a simple synthetic process in which a solubilising group and a group conferring nondiffusion are introduced simultaneously and usually in the final stage of the synthesis. Also the solubilising group in the new couplers may be in a protected form Which often facilitates the isolation and purification of the color couplers. The solubilising groups are readily freed when the compounds are dissolved in alkali prior to the addition to the photographic emulsion, or, if the color couplers are applied as a dispersion, in the alkaline developing bath.
  • A is a trivalent radical selected from B is a color coupling residue
  • X is H or lower alkyl
  • Y is OC, CONH or -COCH when X is H
  • Y is O S when X is lower alkyl
  • R is an alkyl group of 12 or more carbon atoms or a group containing same.
  • color coupler residue used to define the symbol B is meant a grouping such that the compound B-H (and therefore also the compound B.NH is a compound which will react with the oxidation products of N,N-diethyl-p-phenylene diamine, formed during the development of a silver salt image with that compound, to yield a quinone-imine or azamethine dyestuif.
  • color couplers of the general Formula I are obtained by condensing a compound of Formula III:
  • compounds of Formula II are obtained from compounds of Formula I by heating compounds of Formula I in a solvent at a temperature greater than 100 C. and preferably in glacial acetic acid at the boil.
  • compounds of Formula I are obtained from compounds of Formula II by treating with alkali, in a solvent such as a lower alcohol, for example n-propanol, followed by acidification.
  • a solvent such as a lower alcohol, for example n-propanol
  • compounds B-NH 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-methyl-2-aminophenol or the aminophenols described in British patent specifications Nos. 797,141; 754,306; l-amino-S-naphthol, N(B- aminoethyl)-l-hydroxy-2-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. 757,368 and which give cyan dyestuffs on color development with substituted p-phenylene diamines.
  • an amino group for example 4-chloro-5-methyl-2-aminophenol or the aminophenols described in British patent specifications Nos. 797,141; 754,306; l-amino-S-naphthol, N(B- aminoethyl)-l-hydroxy-2
  • photographic light sensitive colloid silver halide emulsions which comprise a color coupler of general Formula I or II.
  • a photographic material for use in color photography which comprises a support carrying a plurality of photographic light sensitive colloid silver halide emulsion layers, selectively sensitive to different regions of the spectrum and comprising in a said emulsion layer or in a layer adjacent thereto, a color coupler of the general Formula I or II.
  • the colloid will generally be gelatin or may be another colloid medium, e.g. polyvinyl alcohol.
  • the multilayer color photographic material may be a natural order material in which the images are to be formed in colors 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 lower 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 color couplers may be incorporated in the photographic emulsion layers by taken them up in dilute alkali, e.g. dilute sodium hydroxide and adding the resulting solution to the emulsion. If the color couplers are of Formula II the alkali has the effect of opening the ring structure:
  • the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for example, the compounds may be dispersed, for
  • EXAMPLE 1 4- (4-dodecylphenylaminocarbonyl -N-( l-phenyl- 5 -pyraZolonyl-3 phthalimide A mixture of 5.25 parts of 1-phenyl-3-amino-5-pyrazolone, 13.5 parts of 4-(4-dodecylphenylaminocarbonyl) phthalic anhydride and 200 parts of glacial acetic acid is heated under reflux for 1 hour. The reaction product which crystallises out on cooling is filtered off and washed well with ethyl acetate.
  • the 4-(4-dodecylphenylaminocarbonyl)phthalic anhydride used in the above example may be prepared as follows:
  • the 4-(4-dodecylphenylaminocarbonyl)phthalic acid itself may be prepared as follows:
  • the phthalimide-4-carboxy chloride itself may be obtained from trimellitic anhydride by reacting first with ammonia and then with thionyl chloride.
  • a photographic layer containing the color coupler may be obtained in the following manner:
  • a mixture of 1.41 parts of the color coupler, 20 parts of n-propanol and 2.4 parts of 2 N potassium hydroxide solution is warmed to dissolve and distilled water added to make 30 parts.
  • the solution of color coupler so obtained is added to 500 parts of a green sensitised gelatin silver halide emulsion containing silver halide equivalent to 2.5 parts of silver and 3.5% gelatin.
  • the emulsion is then coated on a paper base and the coated layer dried.
  • the lonyl-3-)phthalimide are obtained as a light brown solid reaction product obtained on cooling is filtered olf and melting at 176-180 C. On analysis the compound is recrystallised from 2000, parts of methanol. The 12.4 found to contain 71.6% of carbon, 7.8% of hydrogen and parts of 2-carboxy-4-(4-dodecylphenylaminocarbonyl)-N- 9.2% of nitrogen (C H N O requires 72.0% of carbon, [3-(4 methoxybenzoylacetarnide) 4 methoxyphenyl] 8.0% of hydrogen and 9.3% of nitrogen).
  • benzamide are obtained as a colourless solid melting at The 4-(n-octadecylaminocarbonyl)phthalic anhydride 216-218 C.
  • the compound is found to conused in the above example may be prepared as follows: tain 68.3% of carbon, 6.4% of hydrogen and 5.6% of A mixture of 50 parts of 4-(n-octadecylaminocarnitrogen 44 s1 s a ICHaOH requires of bonyl)phthalic acid and 500 parts of acetyl chloride is 13011, 6.9% Of hydroge and g heated under reflux for /2 hour.
  • 10.0 parts of 4- 45 may be repar d as f ll (4-dodecylphenylaminocarbonyl) N [6(1 hydroxy- A mixture of 51 parts of 4-(n-octadecylaminocarbonyl) 2 naphthamido)ethyl]phthalimide are obtained melting phthalimide, 125 parts of 2N sodium hydroxide solution, at 274-275 C. On analysis the compound is found to 750 parts of water and 500 parts of ethanol is heated contain 74.4% of carbon, 7.0% of hydrogen and 6.7% under reflux for 3 hours.
  • the solution obtained is after of nitrogen (C H -N O requires 74.4% of carbon, cooling acidified with 210 parts of 2 N hydrochloric acid 7.0% of hydrogen and 6.5% of nitrogen). and the colorless solid precipitated, is collected by filtra-
  • a photographic layer containing the color coupler may tion and recrystallised from 300 parts of glacial acetic be obtained in the following manner: acid.
  • the 53.2 parts of 4-(n-octadecylaiminocarbonyl) A mixture of 2.4 parts of the color coupler, 16 parts phthalic acid are obtained as a colorless solid melting at of n-propyl alcohol and 3.6 parts of 2 N potassium hy- 55 125-127 C.
  • EXAMPIJE 7 4-(4-dodecylphenylaminocarb onyl) -N(4-wcyanacetylphenyl) phthalimide In place of the 5.25 parts of 1-phenyl-3-amino-5- pyrazolone used in Example 1 there are used 4.4 parts of 4-w-cyanacetylaniline. The 13.9 parts of 4-(4-dodecylphenylaminocarbonyl) N (4 w cyanacetylephenyl) phenyl)phthalimide are obtained as a solid melting at 222-224" C. On analysis the compound is found to contain 7.0% of carbon, 6.5% of hydrogen and 7.2% of nitrogen (C H N O requires 74.9% of carbon, 6.8% of hydrogen and 7.3% of nitrogen).
  • EXAMPLE 8 4-(4-dodecylphenylaminocarb onyl -N-4-methoxy-3- [N- l-phenyl-5-pyrazolonyl-3-)amino] phenyl phthalimide H 0 CH3
  • the reaction product whichcrystallises out on cooling is collected by filtration and recrystallised from ethyl acetate.
  • a photographic layer containing the color coupler may be obtained in the following manner:
  • the coupler is filtered ofl from the reaction mixture and recrystallised from glacial acetic acid.
  • the 15.2 parts of 4-(4-dodecylphenylaminocarbonyl) N ⁇ 4-[N-(1-phenyl-5-pyrazolonyl-3-)aminoacetyl] phenyl ⁇ phthalimide are obtained as a solid melting at 238-240 C.
  • EXAMPLE 10 4- (4-dodecylphenylaminocarbonyl -N- [4-(4-methoxybenzoylacetamido phenyl] phthalimide omo-Q-oo CH2 0 o NHN ⁇
  • the 4-chloro-1-hydr0xy-2-N-(3-aminobenzyl)naphthamide used in the above example may be prepared as follows:
  • a mixture of 15.2 parts of 3-nitrobenzylamine and 29.8 parts of phenyl:l-hydroxy-4-chloro-2-naphthoate is heated at 160170 C. at a pressure of 12 mm. and the phenol formed is distilled off. After cooling the reaction mixture is stirred with methanol, filtered and recrystallised by dissolving in 100 parts of Sellosolve and adding parts of ethanol and 50 parts of water.
  • the 15.8 parts of 4-chloro- 1-hydroxy-2-N(3-nitrobenzyl)napthamide are obtained as a solid melting at 192-194 C.
  • phthalic anhydride 4 N-methyl-N-(4-dodecylphenyl)sulphonamide used in the above example may be prepared as follows:
  • the phthalic acid-4-N-methyl-N-(4-dodecylphenyl)sulphonamide may be prepared as follows:
  • a mixture of 39 parts of phthalic acid-4-N-(4-dodecylphenyl)sulphonamide, 12.9 parts of potassium hydroxide pellets, 380 parts of water and 32.6 parts of methyl iodide is stirred at 20 C. for 1 hour then at 50 C. for 1 hour.
  • the mixture is acidified with 2N hydrochloric acid solution, the colourless precipitate collected by filtration and recrystallised from 50:50 water/ acetic acid mixture.
  • the 38 parts of phthalic acid-4-N-methyl-N-(4-dodecylphenyl) sulphonamide are obtained as a colorless solid melting at l45-146 C.
  • the 1-phenyl-3-(3-amino 4 chloro)benzoylamino-5- pyrazolone used in the above example may be prepared as follows:
  • the 1 phenyl-3-(3-nitro-4-chloro)benzoylamino-5-py razolone itself may be prepared as follows:
  • the S-nitro-Z-chlorobenzoyl chloride may be obtained 20 by heating S-nitro-Z-chlorobenzoic acid with thionyl chloride.
  • EXAMPLE 18 3-carboxy-4-[6-(1-hydroxy-2-naphthamido)hexyl] aminocarbonyl-N- (4-dodecyl phenyl benzamide COOH hydride and 5.7 parts of 1-(l-hydroxy-Z-naphthamido)-6- aminohexane are heated under reflux with 100 parts by volume of dry ethyl acetate for 15-30 minutes. On cooling and filtering oi? the solid deposited 12.4 parts of 3- carboxy-4-[6-(1-hydroxy 2 naphtharnido)hexyl]aminocarbonyl N (4-dodecylphenyl)benzamide are obtained, M.P. 182 dec. On analysis, this compound is found to contain 7.4% of hydrogen and 5.8% of nitrogen (C H N O requires 7.6% of hydrogen and 5.8% of a nitrogen).
  • 'A photographic emulsion layer which contains 2180 parts of the above color coupler, formulated by the method of Example 3 gives a cyan dye image with light absorption maximum of 690 millimicrons.
  • a photographic colloid silver halide emulsion containing a color coupler which is a compound selected from the class consisting of compounds of the Formula I:
  • A is a trivalent radical selected from the class consisting of and in the case where A is the COOH group is ortho to the CONHB group and in the case where A is the COOH group is in one of the positions ortho and peri to the CONHB group
  • X is selected from the class consisting of hydrogen andlower alkyl
  • Y is selected from the class consisting of the linkages OC--, CONH and COCH when X is hydrogen and Y is O S- when X is lower alkyl
  • B is a residue of a compound BNH which will react with the oxidation products of N,N-diethyl p-phenylene diamine, formed during the development with a silver salt image with that compound, to yield a dyestufi image selected from the class consisting of quinone imine and azamethine dyes, said compound BNH being selected from the class consisting of such compounds wherein B contains a COCH -CO- group and the compound gives a yellow dyestulf on color development with substituted p
  • R, X, Y and B have the meanings just assigned and A is a trivalent radical selected from the class conand in the case where A is the two -'CO- groups are ortho to each other and in the case where A is the two CO- linkages are in one of the positions ortho and peri to each other.
  • a photographic material for use in color photography which comprises a support carrying a plurality of photographic light sensitive colloid silver halide emulsion layers selectively sensitive to difierent regions of the spectrum said material containing in operative-contact with said emulsion layer a color coupler which is a compound selected from the class consisting of compounds of the Formula I:
  • A is a trivalent radical selected from the class consisting of:
  • X is selected from the class consisting of hydrogen and lower .alkyl
  • Y is selected from the class consisting of the linkages OC-, CONH and COCH when X is hydrogen and Y is O S when X is lower alkyl
  • B is a residue of a compound BNH which will react with the oxidation products of N,N-diethyl p-phenylene diamine, formed during the development with a silver salt image with that compound, to yield a dyestutf image selected from the class consisting of quinone imine and azamethine dyes
  • said compound BNH being selected from the class consisting of such compounds wherein B contains a -COCH CO- group and the compound gives a yellow dyestutf on color development with substituted p-phenylene diamines, such compounds wherein B contains a
  • R, X, Y and B have the meanings just assigned 13 and A is trivalent radical selected from the class consisting of and in the case where A is the two CO groups are ortho to each other and in the case where A is the two CO- linkages are in one of the positions ortho and peri to each other.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Indole Compounds (AREA)
US432898A 1964-02-20 1965-02-15 Color photography utilizing color couplers which yield quinone imine or azamethine dye images Expired - Lifetime US3383214A (en)

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GB7180/64A GB1039452A (en) 1964-02-20 1964-02-20 Amide colour couplers

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US432898A Expired - Lifetime US3383214A (en) 1964-02-20 1965-02-15 Color photography utilizing color couplers which yield quinone imine or azamethine dye images
US630784A Expired - Lifetime US3547944A (en) 1964-02-20 1967-03-31 Colour photography utilizing colour couplers which yield quinone imine or azamethine dye images

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BE (1) BE659858A (de)
CH (1) CH446060A (de)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3482971A (en) * 1967-07-24 1969-12-09 Polaroid Corp Scavengers for oxidized developing agent
US3711286A (en) * 1968-02-07 1973-01-16 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion
US4040835A (en) * 1974-06-27 1977-08-09 Fuji Photo Film Co., Ltd. Two-equivalent magenta couplers with amido coupling-off groups
US4106940A (en) * 1974-10-03 1978-08-15 Agfa-Gevaert, A.G. Light-sensitive material containing emulsified substances

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
US3278306A (en) * 1960-08-29 1966-10-11 Ilford Ltd Colour couplers and their production and use in colour photography

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2506654A (en) * 1945-01-04 1950-05-09 Firm Teva Chemical Mfg Company Derivatives of 4-amino-antipyrine
GB997500A (en) * 1963-06-17 1965-07-07 Ilford Ltd Improvements in or relating to colour couplers and to their production and use in colour photography

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
US3278306A (en) * 1960-08-29 1966-10-11 Ilford Ltd Colour couplers and their production and use in colour photography

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3482971A (en) * 1967-07-24 1969-12-09 Polaroid Corp Scavengers for oxidized developing agent
US3711286A (en) * 1968-02-07 1973-01-16 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion
US4040835A (en) * 1974-06-27 1977-08-09 Fuji Photo Film Co., Ltd. Two-equivalent magenta couplers with amido coupling-off groups
US4106940A (en) * 1974-10-03 1978-08-15 Agfa-Gevaert, A.G. Light-sensitive material containing emulsified substances

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DE1543048A1 (de) 1969-11-27
NL6502125A (de) 1965-08-23
BE659858A (de) 1965-06-16
CH446060A (de) 1967-10-31
US3547944A (en) 1970-12-15
NL133250C (de)
DE1543048B2 (de) 1975-06-05
GB1039452A (en) 1966-08-17

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