US3843366A - Yellow forming colour couplers for photographic silver halide material - Google Patents

Yellow forming colour couplers for photographic silver halide material Download PDF

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Publication number
US3843366A
US3843366A US00232185A US23218572A US3843366A US 3843366 A US3843366 A US 3843366A US 00232185 A US00232185 A US 00232185A US 23218572 A US23218572 A US 23218572A US 3843366 A US3843366 A US 3843366A
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colour
water
silver halide
melting point
chain
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Expired - Lifetime
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US00232185A
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English (en)
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Poucke R Van
G Benoy
Cat A De
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Agfa Gevaert NV
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Agfa Gevaert NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • 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

  • X represents hydrogen or a group that exhibits two-equivalent character on colour development
  • R and R represent straight-chain or branched-chain alkyl having from 1 to about 20 C-atoms
  • Y stands for COOR wherein R and R represent a straight-chain or branched-chain alkyl group of which the carbon chain may be interrupted by oxygen, and R R R and R represent hydrogen or have the same significance given for R and R They are described for use as colour couplers in lightsensitive silver halide emulsions where, upon colour clevelopment, they yield dyes with excellent spectral characteristics and high stability.
  • This invention relates to the production of photographic colour images, to colour couplers for yellow used therein and to photographic materials containing such colour couplers.
  • a light-sensitive photographic colour material containing a red-sensitized, a green-sensitized and a blue-sensitive silver halide emulsion layer wherein on colour development, by use of appropriate colour couplers, a cyan, magenta and yellow dyestuff image are formed respectively.
  • Colour couplers for yellow of the benzoylacetarylide type having an o-alkoxy-substituent in the benzoyl part of the molecule generally yield upon colour development dyes having a higher stability than those containing in the benzoyl part a p-alkoxy substituent or no alkoxy substituent at all.
  • Another object of the present invention is to provide colour couplers for yellow having favourable spectral properties i.e. colour couplers which produce upon colour development yellow azomethine dyes with very low sideabsorption in the green and red region of the spectrum.
  • a further object of the present invention is to provide colour couplers which produce upon colour development yellow azornethine dyes with hypsochromic absorption maxrma.
  • X represents a hydrogen atom or .a substituent that exhibits two equivalent character on colour development e.g. a halogen atom, an SR' group wherein R' is alkyl, substituted alkyl, aryl, substituted aryl, a heterocycle or a substituted heterocycle or an -OR" group wherein R represents alkyl, substituted alkyl, aryl, substituted aryl, acyl or substituted acyl, e.g. acetyl and benzoyl,
  • R and R represent a branched-chain or straight-chain alkyl having from 1 to about 20 C-atoms
  • Y represents COOR R4 R1 CON SOzRa 0! SOzN a Ra wherein R and R represent a straight chain or branched-chain alkyl group of which the carbon chain may be interrupted by oxygen, and R R R and R rep resent hydrogen or have the same significance given for R and R -COCH2CONH COOCH:
  • Colour coupler 4 This colour coupler was prepared by condensation of o-methoxy-benzoyl acetic acid ethyl ester and 3-methoxy-4-aminobenzoic acid n-hexa-- decyl ester according to the method of preparation 1. Recrystallization occurred from cyclohexane. Melting point: 86 C.
  • PREPARATION 7 Colour coupler 7 (a) 3-methoxy-4-amino-benzoic acid fi-methoxyethyl ester.--108 g. of 3-methoxy-4-amino-benzoic acid methyl ester, 150 ml. of ethylene glycol monomethyl ether and 2.5 ml. of titanium tetrabutoxide were boiled for 16 hours while introducing nitrogen and distilling off the methanol formed. The excess of alcohol was removed and the residue recrystallized from n-hexane. Melting point: 60 C.
  • the acetanilide was hydrolyzed in 50 ml. of 5N hydrochloric acid and 50 ml. of ethanol. After having refluxed the reaction mixture for 2 hours it was neutralized by addition of ammonium hydroxide. The precipitate formed was filtered OH and recrystallized from methanol. Melting point: 74 C.
  • the precipitate was boiled for 2 hours in 400 ml. of ethanol and 480 ml. of 5N hydrochloric acid whereupon the mixture was neutralized by addition of ammonium hydroxide.
  • the precipitate was filtered otf, dried and recrystallized from acetonitrile. Melting point: 135 C.
  • the yellow colour formers according to the present invention are of the non-diffusible type; they comprise in their molecule at least one acyclic aliphatic hydrocarbon group sufficiently large for preventing the colour coupler of wandering from the colloid layer, in which the coupler is incorporated, to another colloid layer.
  • the non-diffusion colour couplers for each colour separation image are usually incorporated into the coating compositions of the differently sensitized silver halide emulsion layers.
  • the non-diffusing colour couplers may also be added to the coating compositions of non-light-sensitive colloid layers which are in water-permeable relationship with the light-sensitive silver halide emulsion layers e.g. in layers which are in direct contact with the light-sensitive layers or which are separated from said light-sensitive layers by Water-permeable non-lightsensitive layers.
  • the non-migratory yellow forming colour couplers according to the above general formulae can be incorporated in the coating composition of the silver halide emulsion layers or other colloid layers in waterpermeable relationship therewith according to any technique known by those skilled in the art for incorporating water-insoluble photographic ingredients, more particularly water-insoluble colour couplers, into colloid compositions.
  • the colour couplers can be incorporated into the coating composition of the layer in question from a solution in the appropriate water-miscible or water-immiscibel high-boiling or low-boiling organic solvent or mixture of these solvents whereupon the solution obtained is dispersed, if necessary in the presence of a wetting or dispersing agent, in a hydrophilic colloid composftion forming or forming part of the binding agent of the colloid layer.
  • the hydrophilic colloid composition may of course comprise in addition to the colloid carrier all other sorts of ingredients.
  • the solution of said colour coupler need not necessarily be dispersed directly in the coating composition of the silver halide emulsion layer or other water-permeable layer.
  • Said solution may advantageously be first dispersed or dissolved in an aqueous non-light-sensitive hydrophilic colloid solution whereupon the resultant mixture, after the removal (if necessary) of the organic solvents employed, is intimately mixed with the said coating composition of the light-sensitive silver halide emulsion layer or other water-permeable layer just before coating.
  • the colour couplers of the invention are preferably incorporated into hydrophilic colloid media from solutions in high-boiling sparingly water-miscible solvents such as di-n-butyl phthalate and tricresyl phosphate or in low-boiling sparingly water-miscible solvents such as ethyl acetate, methylene cholride, chloroform, etc. or mixtures thereof in that they have a high solubility therein and very fine dispersions in hydrophilic colloid compositions of the colour couplers of the invention can be obtained by means of these solvents.
  • these solutions are dispersed in extremely fine droplets in the presence of a wetting or dispersing agent into the hydrophilic colloid medium the low-boiling sparingly water-miscible solvent then being removed by evaporation.
  • the couplers according to the invention may be used in conjunction with various kinds of photographic emulsions.
  • Various silver salts may be used as the sensitive salt such as silver bromide, silver iodide, silver chloride or mixed silver halides such as silver chlorobromide, silver bromoiodide and silver chlorobromoiodide.
  • the couplers can be used in emulsions of the mixed packet type as described in United States Patent Specification 2,698,794 or emulsions of the mixed grain type as described in United States Patent Specifictaion 2,592,243.
  • the colour couplers can be used with emulsions wherein latent images are formed predominantly on the surface of the silver halide crystal, or with emulsions wherein latent images are formed predominantly inside the silver halide crystal.
  • the hydrophilic colloid used as the vehicle for the silver halide may be, for example, gelatin, colloidal albumin, zein, casein, a cellulose derivative, a synthetic hydrophilic colloid such as polyvinyl alcohol, poly-N-vinyl pyrrolidone, etc. If desired, compatible mixtures of two or more of these colloids may be employed for dispersing the silver halide.
  • the light-sensitive silver halide emulsions of use in the preparation of a photographic material according to the present invention may be chemically as well as optically sensitized. They may be chemically sensitized by effecting the ripening in the presence of small amounts of sulphur containing compounds such as allyl thiocyanate, allyl thiourea, sodium thiosulphate, etc.
  • the emulsions may also be sensitized by means of reductors for instance tin compounds as described in French Patent Specification 1,146,- 955 and in Belgian Patent Specification 568,687, iminoamino methane sulphinic acid compounds as described in United Kingdom Patent Specification 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium compounds. They may be optically sensitized by means of cyanine and merocyanine dyes.
  • reductors for instance tin compounds as described in French Patent Specification 1,146,- 955 and in Belgian Patent Specification 568,687, iminoamino methane sulphinic acid compounds as described in United Kingdom Patent Specification 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium compounds. They may be optically sensitized by means of cyanine and merocyanine
  • the said emulsions may also comprise compounds which sensitize the emulsions by development acceleration for example compounds of the polyoxyalkylene type such a as alkylene oxide condensation products as described among others in United States Patent Specifications 2,531,832, 2,533,990, 3,210,191 and 3,158,484, in United Kingdom Patent Specifications 920,637, and 991,608 and in Belgian Patent Specification 648,710 and onium derivatives of amino-N-oxides as described in Untied Kingdom Patent Specification 1,121,696.
  • compounds of the polyoxyalkylene type such a as alkylene oxide condensation products as described among others in United States Patent Specifications 2,531,832, 2,533,990, 3,210,191 and 3,158,484, in United Kingdom Patent Specifications 920,637, and 991,608 and in Belgian Patent Specification 648,710 and onium derivatives of amino-N-oxides as described in Untied Kingdom Patent Specification 1,121,696.
  • the emulsions may comprise stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and 1-phenyl-2-tetrazoline-5- thione and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Patent Specifications 524,121, 677,337 and 707,- 386 and in United States Patent Specification 3,179,520.
  • stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and 1-phenyl-2-tetrazoline-5- thione and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Patent Specifications 524,121, 677,337 and 707,- 386 and in United States Patent Specification 3,179,520.
  • the light-sensitive emulsions may also comprise all other kinds of ingredients such as plasticizers, hardening agents, wetting agents, etc.
  • the non-diifusing yellow colour formers described in the present invention are usually incorporated into the blue-sensitive silver halide emulsion for forming one of the differently sensitized silver halide emulsion layers of a photographic multilayer colour material.
  • a photographic multilayer colour material usually comprises a support, a red-sensitized silver halide emulsio layer with a cyan colour former, a green-sensitized silver halide emulsion layer with a magenta colour former and a bluesensitive silver halide emulsion layer with a yellow colour former.
  • the emulsions can be coated on a wide variety of photographic emulsion supports.
  • Typical supports include cellulose ester film, polyvinylacetal film, polystyrene film, polyethylene terephthalate film and related films or resinous materials, as well as paper and glass.
  • an exposed silver halide emulsion layer is developed with an aromatic primary amino developing substance in the presence of a colour coupler according to the present invention.
  • All colour developing agents capable of forming azomethine dyes can be utilized as developers.
  • Suitable developing agents are aromatic primary amino compounds for example N,N-dialkylp-phenylene diamines and derivatives thereof e.g. the toluene analogues.
  • Typical examples of aromatic primary amino colour developing agents are: N,N-diethylp-phenylene diamine, Z-amino-5-diethylaminotoluene, N-
  • the yellow colour formers according to the invention form on colour development yellow azomethine dyes which excell by their favourable light absorption in the blue region of the spectrum and little absorption in the other regions of the spectrum. Furthermore, the colour couplers manifest a high activity during development i.e., they furnish colour images with high colour density.
  • the latter colour coupler has a melting point of 71 C. and was prepared in a similar way as the colour couplers of the invention by condensation of 104.5 g. of o-hexadecyloxybenzoylacetic acid methyl ester and 41 g. of p-aminobenzoic acid ethyl ester in 190 ml. of xylene.
  • the emulsions were coated on a film support pro rata of g. per sq. m.
  • the emulsion layers were dried and overcoated with a gelatin antistress layer.
  • the yellow dye image formed in accordance with the present invention shows good resistance to heat and humidity.
  • Example 2 Two emulsions are prepared as described in Example 1. Emulsion A contains per kg. 0.006 mole of colour coupler 1 and emulsion B contains per kg. 0.006 mole of the colour coupler with formula:
  • Example 3 This example is analogous to Example 2 with the difference that processing occurs as follows.
  • Borax 20 Anhydrous potassium bromide 15 Anhydrous sodium bisulphate 4.2 Potassium hexacyanoferrate(III) Water to make 1 litre.
  • the emulsion was coated on a film support pro rata of g. per sq. m.
  • the emulsion layer was dried and overcoated with a gelatin antistress layer.
  • Example 4 Colour coupler used- '7 max- 7 umb 'y ina!- Colour coupler 3 0. 83 1. 65 0.63 1. 63 0.77 1. 55 Comparison colour coupler 0.51 1. 27 0. 49 1. 29 0.61 l. 23
  • X represents hydrogen, halogen, S-R and O-R" wherein R is alkyl, aryl, or heterocycle, and R" is alkyl, aryl, or acyl,
  • R and R represent straight-chain or branched-chain alkyl having from 1 to about 20 C-atoms
  • Y stands for COOR R4 CON 30 m or SO N wherein R and R represent a straight-chain or branched-chain alkyl group or an alkoxy alkyl group, and R R R and R represent hydrogen or have the same significance given for R and R the colour coupler molecule comprising at least one alkyl group rendering the molecule fast to diffusion in hydrophilic colloid media.
  • Photographic colour material according to claim 1 wherein the said material is a multilayer colour material comprising three silver halide emulsion layers which have a different spectral sensitivity, including a blue-sensitive silver halide emulsion layer, the said blue-sensitive silver halide layer or a non-light-sensitive water permeable colloid layer adjacent thereto incorporating the said colour coupler(s).
  • X represents hydrogen, halogen, -SR' and -OR" wherein R is alkyl, aryl, or heterocycle, and R" is alkyl, aryl, or acyl,
  • R and R represent straight-chain or branched-chain alkyl having from 1 to about 20 C-atoms
  • Y stands for COOR wherein R and R represent a straight-chain or branched-chain alkyl group or an alkoxy alkyl group, and R R R and R represent hydrogen or have the same significance given for R and R the said colour coupler(s) being present in a blue-sensitive silver halide emulsion layer or other colloid layer in water-permeable relationship therewith of the said photographic element.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00232185A 1971-03-25 1972-03-06 Yellow forming colour couplers for photographic silver halide material Expired - Lifetime US3843366A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712114578 DE2114578A1 (de) 1971-03-25 1971-03-25 Fotografischer Gelbkuppler

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US (1) US3843366A (enExample)
BE (1) BE780164A (enExample)
DE (1) DE2114578A1 (enExample)
FR (1) FR2130156B1 (enExample)
GB (1) GB1379813A (enExample)
IT (1) IT960497B (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966475A (en) * 1973-04-06 1976-06-29 Agfa-Gevaert N.V. Photographic silver halide emulsions containing acylacetanilide color couplers
US3998641A (en) * 1973-12-10 1976-12-21 Agfa-Gevaert, A.G. Photographic material containing yellow couplers
US4193559A (en) * 1978-04-07 1980-03-18 E. I. Du Pont De Nemours And Company Film web winding assembly
US4617256A (en) * 1984-11-14 1986-10-14 Agfa Gevaert Aktiengesellschaft Color photographic color coupler-containing recording material

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966475A (en) * 1973-04-06 1976-06-29 Agfa-Gevaert N.V. Photographic silver halide emulsions containing acylacetanilide color couplers
US3998641A (en) * 1973-12-10 1976-12-21 Agfa-Gevaert, A.G. Photographic material containing yellow couplers
US4193559A (en) * 1978-04-07 1980-03-18 E. I. Du Pont De Nemours And Company Film web winding assembly
US4617256A (en) * 1984-11-14 1986-10-14 Agfa Gevaert Aktiengesellschaft Color photographic color coupler-containing recording material

Also Published As

Publication number Publication date
FR2130156A1 (enExample) 1972-11-03
DE2114578A1 (de) 1972-10-05
GB1379813A (en) 1975-01-08
BE780164A (nl) 1972-09-04
IT960497B (it) 1973-11-20
FR2130156B1 (enExample) 1976-10-29

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