US3884700A - Silver halide emulsions containing two-equivalent benzoylacetanilide photographic couplers - Google Patents

Silver halide emulsions containing two-equivalent benzoylacetanilide photographic couplers Download PDF

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US3884700A
US3884700A US318561A US31856172A US3884700A US 3884700 A US3884700 A US 3884700A US 318561 A US318561 A US 318561A US 31856172 A US31856172 A US 31856172A US 3884700 A US3884700 A US 3884700A
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coupler
couplers
moles
silver halide
benzoylacetanilide
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Andrea Quaglia
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3M Co
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Minnesota Mining and Manufacturing Co
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • 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
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to two-equivalent benzoylacetanilide couplers for color photography and to colored photographic elements containing them.
  • the present invention relates to two-equivalent benzoylacetanilide couplers which give rise to yellow dyes upon color development with pphenylene diamine type developers.
  • the present invention further relates to photographic emulsions containing such couplers. to photographic elements including such emulsions and to photographic elements containing the dyes derived from such couplers upon color development.
  • Colored photographic elements normally include at least three emulsion layers which are sensitive to the blue, to the green and to the red region and contain, respectively, a yellow, a magenta and a cyan coupler.
  • couplers used in photographic elements should not be excessively reactive. This will prevent undesired color formations.
  • couplers must give rise upon color development to dyes having a given desired absorption curve to obtain images with balanced colors It may be useful, for instance, to obtain yellow dyes substantially without orange colorations, i.e., with a low absorption in the green region.
  • Benzoylacetanilide type couplers are capable of reacting with the oxidation product of p-phenylene diamine type developers to form yellow images in light exposed silver halide photographic elements.
  • a molecule of such couplers normally give rise to a molecule of a dye by the reduction of four silver ions struck by the light. If however one of the hydrogens of the reactive methylene in the coupler is substituted with a suitable substituent, a molecule of a dye can be obtained by the reduction of only two silver ions.
  • couplers which exhibit such characteristics are commonly called two-equivalent couplers: the meaning of this expression is clear. Obviously they are very useful in color photographic industry because they allow a lower consumption of silver in color photographic emulsions which employ incorporated couplers.
  • Benzoylacetanilide couplers include a benzoyl residue (phenyl-CO) and an aniline residue (NH-phenyl) joined by a carboxymethylene bridge (CHg-CO). This methylene group is called reactive methylene" be cause the coupling reaction occurs on it.
  • Such two-equivalent benzoylacetanilide couplers have some drawbacks which make their practical employment in colored photographic elements difficult and sometimes impossible. These difficulties drive from their excessive reactivity which enables them to react with the developer even in absence of exposed silver halide, thus giving rise to undesired coloration commonly called fog. Furthermore, some two-equivalent benzoylacetanilide couplers known in the art are much more expensive than four-equivalent couplers from LII ' low-cost couplers substantially free of fog can be obtained by the combination of a halogen substituent (Y) in ortho position in the benzoyl and a halogen substituent (X) in the reactive methylene.
  • the halogen substituent (X) produces low-cost twoequivalent couplers, and the halogen substituent (Y), combined with it, yields two-equivalent couplers substantially free of fog.
  • the halogen substituent in ortho position in the benzoyl is an essential substituent for the purposes of the present invention. It enables one to obtain, free of fog, two-equivalent benzoylacetanilide couplers of the type having a hydrogen of the reactive methylene substituted with a halogen.
  • Substituents which can be usefully introduced into the molecule of the couplers of the present invention are for instance alkyl groups (having for instance from 1 to 18 carbon atoms), halogen (for instance Cl, Br, F), alkoxy groups (having for instance from I to 18 carbon atoms), dialkylamino groups (having from 2 to 19 carbon atoms), arylaminosulphoxy groups (for instance phenylaminosulphoxy, alkylphenylaminosulphoxy, oand p-alkylphenylaminosulphoxy, oand palkoxyphenylaminosulphoxy, wherein the alkyl or alkoxy group has from 1 to 18 carbon atoms), aryloxyacylamino group (for instance phenyloxyacylamino, phenyloxyacetylamino, alkylphenyloxyacylamino, 2,4- dialkyl-phenyloxyacylamino, 2,4- dialkylphenylacetylamino,
  • two-equivalent couplers free of fog which give rise to yellow dyes substantially without orange coloration upon color development with pphenylene diamine type developers is the combination of a fluorine atom in the ortho position in the benzoyl, a halogen in the reactive methylene and an electron donor of the alkyl, alkoxy group, dialkylamino type and their equivalents in ortho position in the aniline residue.
  • Very stable couplers within the present invention can be further obtained if in combination with the halogen, particularly fluorine atom in ortho position in the benzoyl, the halogen in the reactive methylene and the electron donor of the alkyl, alkoxy group and dialkylamino type in 2 (ortho) position in the aniline residue, an arylsulphonamiclo or arylaminosulphoxy group in S-position in the aniline residue (for instance phenylaminosulphoxy, alkylphenylaminosulphoxy, alkoxylaminosulphoxy, oand palkylphenylaminosulphoxy, oand palkoxyphenylaminosulphoxy, phenylsulphonamido, alkylphenylsulphonamido, alkoxyphenylsulphonamido, and p-alkylphenylsulphonamido, oand p-alkoxyphenylsulphonamido, wherein the alkyl or alkoxy
  • the coupler is intended to mean a non-diffusing coupler," Le, a coupler carrying at least a ballasting group capable of imparting non-diffusing properties to the said coupler.
  • the ballasting group is preferably introduced into the aniline residue, preferably into the phenyl ring in ortho (2) and/or in meta (5) position to the carbon atom carrying the amino group (briefly: in ortho and/or in meta position in the aniline residue).
  • the couplers of the present invention must be incorporated into photographic emulsions in aqueous solution, they must be made water-soluble by means of the SO H and COOH type. In the case where they must be incorporated into the emulsion by the solvent dispersion technique, the couplers must be soluble in substantially water-immiscible organic solvents (see: C. E. Kenneth Mees and T. H. James, The Theory of Photographic Process, third edition, page 303).
  • the solvent dispersion technique involves first dissolving a coupler in a substantially water-immiscible organic solvent and then dispersing the so-prepared solution as extremely fine droplets in a hydrophilic colloidal binder.
  • Gelatin is the preferred hydrophilic colloidal binder but other polymeric colloidal binder materials known to the art can also be used.
  • the couplers are incorporated into the emulsion by the solvent dispersion technique, the dyes deriving therefrom upon color development are also contained dispersed in the emulsion dissolved in the substantially water-immiscible organic solvent.
  • the present invention refers, in its most general aspects, to non-diffusing benzoylacetanilide couplers including a halogen atom in the reactive methylene and in ortho position in the benzoyl residue as expressed by the following formula:
  • B is a benzoyl residue bearing a halogen substituent in the phenyl in the ortho position to the carbon atom carrying the carbonyl;
  • X represents a halogen atom and
  • A is an aniline residue.
  • the present invention refers to non-diffusing benzoylacetanilide couplers containing a halogen substituent in the reactive methylene and a fluorine atom in ortho position in the benzoyl. More particularly, the present invention relates to non-diffusing couplers of the benzoylacetanilide type including a halogen atom, and in particular a fluorine atom, in ortho position in the benzoyl, a halogen atom in the reactive methylene and an electron donor of the alkyl group, alkoxy group, dialkylamino group type in ortho position in the aniline residue.
  • the present invention refers to non-diffusing couplers of the benzoylacetanilide type including a halogen atom, and in particular a fluorine atom, in ortho position in the benzoyl residue, a halogen atom in the reactive methylene, an electron donor of the alkyl group, alkoxy group, dialkylamino group type in 2-position in the aniline residue and a group of the arylsulphonamido or arylaminosulphoxy type in S-position in the same aniline residue.
  • a halogen atom and in particular a fluorine atom, in ortho position in the benzoyl residue
  • a halogen atom in the reactive methylene an electron donor of the alkyl group, alkoxy group, dialkylamino group type in 2-position in the aniline residue and a group of the arylsulphonamido or arylaminosulphoxy type in S-position in the same aniline residue.
  • the present invention also relates to silver halide photographic emulsions containing such couplers preferably introduced by the solvent dispersion technique and to photographic elements comprising such emulsions.
  • the present invention further relates to exposed and developed silver halide photographic elements containing dyes derived from the said couplers upon coupling reaction with p-phenylene diamine type compounds.
  • EXAMPLE 1 a-( Z-chlorobenzoyl)-a-chloro-5-[ oz-( 2-4-ditertamylphenoxyl)-acetamide1-2-chloroacetanilide intermediate l; 3-nitro-4-chloro-a-(2-4-ditertamylphenoxy )-acetanilide 0 1mg S12E25 5L7 g. (0.3 moles) of 3-nitro-4-chloro-aniline, 29.5 g. (0.36 moles) of sodium acetate anhydrous and 450 m]. of glacial acetic acid were mixed in a multi-neck flask of 1 liter provided with a stirrer and a refluxecondenser.
  • This coupler was prepared in the manner described in Example 1.
  • Coupler 3 This coupler was obtained in the same manner as coupler 1.
  • EXAMPLE 5 a-( 2-chlorobenzoyl)-a-ch1oro-2-cetoxyacetani1ide Intermediate 1 l; Z-cetoxy-nitrobenzene 8.3 g. (0.36 moles) of metallic sodium were added in small portions into a 1 l. multi-neck flask provided with a stirrer, a thermometer, a dropping funnel and refluxe-condenser and containing 325 ml. of cellosolve. The mixture was stirred till a complete solution was reached and cooled at 20C. 50 g. (0.36 moles) of onitrophenol were then added thereto in small portions. After 30 minutes of stirring, 110.5 g.
  • Coupler This coupler was prepared in the same manner as coupler l. r
  • Coupler 6 This coupler was prepared in the same manner as coupler l.
  • 21 g. of the product were obtained from 25 g. (0.035 moles) of intermediate 18 and 4.7 g. (0.035 moles) of sulphoryl chloride. M.P. 4347C.
  • Coupler 9 This product was obtained in the same manner as coupler 1.
  • This coupler was prepared in the same manner as coupler l.
  • EXAMPLE 12 a-( 2-fluorobenzoyl )-a-chloro-5- a-( 2-4- ditertamylphenoxy )-acetamidel-2-methoxyacetanilide
  • Intermediate 28 a-(2-fluorobenzoyl)-5-[a-(2-4- ditertam ylphenoxy )-acetamide Z-methoxyac etanilide This product was obtained like intermediate 6.
  • This coupler was prepared like what is described in the above-mentioned couplers.
  • This product was prepared according to the method described in the 1. pr. Chem. [2 74, I05.
  • the product had a M.P. 59-61C.
  • the coupler of example 15 was obtained upon reaction of the last intermediate with sulforyl chloride at room temperature with chloroform as a solvent, like that described for the hereinbefore described couplers.
  • the final coupler was a white powder crystallized from methanol. M.P. l37-139C.
  • the couplers of the present invention may be used in conjunction with many types of silver halide emulsions suitable for color photography. They can be used for instance in silver bromide, silver chloride or silver iodide emulsions or in those emlsions containing a halide mixture, such as silver bromoiodide or silver chlorobromide emulsions.
  • the couplers can also be used in those emulsions which are described in U.S. Pat. Nos. 2,592,243 and 2,698,794. Such couplers can still be used in those emulsions capable of forming an image on the surface or in the interior of the silver halide grains, such as those described in U.S. Pat. No. 2,592,250.
  • the abovementioned emulsions can be chemically sensitized either by addition of sulphur compounds, as described for instance in U.S. Pat. Nos. 1,574,944; 1,623,469 and 2,410,689; and by addition of noble metal salts, such as rhutenium, rhodium, iridium, palladium and platinum.
  • noble metal salts such as rhutenium, rhodium, iridium, palladium and platinum.
  • Such emulsions can be chemically sensitized by addition of Au salts, as described in U.S. Pat. No. 2,399,083. They can be stabilized with An salts as described in U.S. Pat. Nos. 2,597,856 and 2,587,915.
  • emulsions can be optically sensitized with apomerocyanine dyes as those described in German Pat. No. 1,009,020; in British Pat. No. 734,792; in French Pat. Nos. 1,559,295 and 2,018,196; in U.S. Pat. No. 3,574,631 and in Belgian Pat. Nos. 746,342 and 747,781.
  • the emulsions can contain organic stabilizers and anit-foggants of the cyclic amine type; iminoazoles, such as mercaptobenzimidazole; triazoles, such as those described in U.S. Pat. No. 2,444,608; azaindenes,
  • mercaptobenzothiazoles such as l-methyl-mercaptobenzothiazole
  • oxazoles thiosemicarbazydes
  • primidines iodonium derivatives
  • benzensulphyn acids inorganic stabilizers of the zinc and cadmium salt type, such as those described in U.S. Pat. Nos. 2,839,405.
  • the emulsions can further contain any suitable plasticizer, known to the man skilled in the art, such as glycerm.
  • the emulsion may be hardened with any suitable hardener for gelatin, known to the man skilled in the art, such as aldehyde of the formaldehyde, glyoxale, succinic, glutaric and resorcylic aldehyde type; and halogen substituted aliphatic acids, such as mucochloric and mucobromic acids, as described in U.S. Pat. No. 2,080,019; or mixtures thereof, as described in U.S. Pat. No. 2,591,542.
  • any suitable hardener for gelatin known to the man skilled in the art, such as aldehyde of the formaldehyde, glyoxale, succinic, glutaric and resorcylic aldehyde type; and halogen substituted aliphatic acids, such as mucochloric and mucobromic acids, as described in U.S. Pat. No. 2,080,019; or mixtures thereof, as described in
  • the emulsions may have been supplied with a coating aid, known to the man skilled in the art, such as saponin.
  • a coating aid known to the man skilled in the art, such as saponin.
  • Any suitable base type known to the man skilled in the art, can be used, such as cellulose triacetate, polyester, paper, polytenated paper.
  • the dispersing agent for the silver halide in its preparation gelatin or another water-permeable means of the colloidal albumin type, a cellulose derivative, or a synthetic resin of the polyvinyl type.
  • Such material types are described in U.S. Pat. Nos. 2,286,215; 2,328,808; 2,322,085; 2,527,872; 2,541,474; 2,563,791; 2,768,154; 2,808,331; 2,852,382.
  • colloids may be employed for dispersing the silver halide in its preparation.
  • the developing baths to be used in conjunction with the couplers of the invention are well-known to the man skilled in the art. They contain a developer of the p-phenylene diamine type, a development restrainer of the potassium bromide type, an antioxidant, such as sodium sulphite and an alkaline agent of the alkali hydrate or carbonate type. They may further contain both an antifoggant of the benzimidazole type and derivatives, of the benzothiazole type and derivatives, of the triazole and tetrazole type and derivatives, such as mercapto-derivatives; and an anticalcium substance of the alkaline phosphate and alkylendiaminopolyacetic acid type, such as for instance EDTA.
  • Suitable developers which can be employed to develop photographic elements, containing the couplers of the present invention, are the sulphites, the hydrochlorides and the sulphates of:
  • EXAMPLE 16 6 g. of each coupler of the present invention and of the couplers A, B, C and D of the type known in the prior art were dissolved in 10 ml. of dibutylphtalate and 16 ml. of ethyl acetate and each solution was emulsified with 60 ml. of a 4 percent gelatin solution.
  • the resulting emulsion was coated on a transparent cellulose acetate base and dried.
  • the following table shows both the for values for each coupler examined in both specimen series A and B and the values corresponding to the fog differences (A V) between both series.
  • the same table also shows the maximum absorption (A max), the maximum density (Dmax), and the A D% (wherein D 1.5) values referring to the specimens of series A.
  • Silver halide photographic emulsions containing dispersed therein at least a coupler of claim 1 dissolved in a substantially water-imiscible organic solvent are dissolved in a substantially water-imiscible organic solvent.
  • Photographic elements including. a base and at least one layer of silver halide photographic emulsion of claim 1.

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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)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US318561A 1971-12-28 1972-12-26 Silver halide emulsions containing two-equivalent benzoylacetanilide photographic couplers Expired - Lifetime US3884700A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT55062/71A IT945697B (it) 1971-12-28 1971-12-28 Copulanti benzoilacetanilidici due equivalenti ed elementi fotografici a colore che li contengono

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US (1) US3884700A (xx)
JP (1) JPS4877832A (xx)
BE (1) BE793424A (xx)
CA (1) CA993887A (xx)
CH (1) CH607108A5 (xx)
DE (1) DE2263587A1 (xx)
FR (1) FR2166047A1 (xx)
GB (1) GB1421181A (xx)
IT (1) IT945697B (xx)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072525A (en) * 1975-08-08 1978-02-07 Fuji Photo Film Co., Ltd. Silver halide photographic material containing two-equivalent color coupler
US4822724A (en) * 1986-12-18 1989-04-18 Minnesota Mining And Manufacturing Company Process for the formation of stable color photographic images
US4824773A (en) * 1986-04-23 1989-04-25 Fuji Photo Film Co., Ltd. Silver halide color photographic material

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56164343A (en) * 1980-05-22 1981-12-17 Konishiroku Photo Ind Co Ltd Color photographic sensitive silver halide material

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056675A (en) * 1959-09-17 1962-10-02 Gen Aniline & Film Corp Benzoyl acetanilide couplers
US3369895A (en) * 1960-08-24 1968-02-20 Eastman Kodak Co Two equivalent yellow couplers for color photography
US3664841A (en) * 1969-11-28 1972-05-23 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion containing yellow-forming coupler
US3669671A (en) * 1969-12-12 1972-06-13 Konishiroku Photo Ind Light-sensitive silver halide photographic emulsions containing yellow couplers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056675A (en) * 1959-09-17 1962-10-02 Gen Aniline & Film Corp Benzoyl acetanilide couplers
US3369895A (en) * 1960-08-24 1968-02-20 Eastman Kodak Co Two equivalent yellow couplers for color photography
US3664841A (en) * 1969-11-28 1972-05-23 Konishiroku Photo Ind Light-sensitive silver halide color photographic emulsion containing yellow-forming coupler
US3669671A (en) * 1969-12-12 1972-06-13 Konishiroku Photo Ind Light-sensitive silver halide photographic emulsions containing yellow couplers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072525A (en) * 1975-08-08 1978-02-07 Fuji Photo Film Co., Ltd. Silver halide photographic material containing two-equivalent color coupler
US4824773A (en) * 1986-04-23 1989-04-25 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US4822724A (en) * 1986-12-18 1989-04-18 Minnesota Mining And Manufacturing Company Process for the formation of stable color photographic images

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IT945697B (it) 1973-05-10
FR2166047A1 (xx) 1973-08-10
CH607108A5 (xx) 1978-11-30
JPS4877832A (xx) 1973-10-19
BE793424A (fr) 1973-06-28
DE2263587A1 (de) 1973-07-19
GB1421181A (en) 1976-01-14
CA993887A (en) 1976-07-27

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