US3393041A - Multilayer silver halide elements containing thiazole color couplers for yellow - Google Patents

Multilayer silver halide elements containing thiazole color couplers for yellow Download PDF

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Publication number
US3393041A
US3393041A US381260A US38126064A US3393041A US 3393041 A US3393041 A US 3393041A US 381260 A US381260 A US 381260A US 38126064 A US38126064 A US 38126064A US 3393041 A US3393041 A US 3393041A
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United States
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group
color
silver halide
yellow
halide emulsion
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US381260A
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English (en)
Inventor
Verbrugghe Marcel Hendrik
Cat Arthur Henri De
Roosen Raymond Albert
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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
    • C07D277/82—Nitrogen atoms

Definitions

  • the color couplers are 2-(aroylacetamido)-thiazoles having at least one sulphonic acid group on the aroyl moiety.
  • the color couplers when employed in photographic materials exhibit an unusually high degree of stability to the action of light, heat and humidity.
  • This invention is concerned with the production of photographic color images, with the color couplers for yellow utilised therein and with photographic materials comprising such color couplers.
  • a light-sensitive photographic color material comprising a silver halide emulsion layer sensitised to red light, a silver halide emulsion layer sensitised to green light and a silver halide emulsion layer sensitised to blue light, in which emulsion layers are formed a cyan, a magenta, and a yellow dye image by using appropriate color couplers during the color development.
  • color couplers must satisfy various requirements according to the method by which the color material is manufactured and the purpose for which it is used.
  • the color couplers ought to be present in the hydrophilic silver halide emulsion layers in non-migratory form.
  • This object can be accomplished e.g. by the use of a, sufliciently water-soluble color coupler comprising an organic radical sufiiciently large to prevent the color coupler from diffusing in the hydrophilic silver halide emulsion layer, or by the utilisation of a lipophilic color coupler, which in dissolved state in a high- -boiling organic solvent is dispersed in the silver halide emulsion layer.
  • a new class of color couplers for yellow of the ketomethylene type, more particularly 2-(aroylacetamido)- thiazole derivatives has been found now. These color couplers display a high activity during color development and form yellow dyes possessing a favorable resistance to humidity and heat.
  • These 2-(aroylacetamido)-thiazole derivatives are characterised by the presence of at least one group solubilising in water, more particularly a sulphonic acid group in the aroyl part of the molecule.
  • the sulphonic acid gr0up(s) can be implanted directly in the aromatic nucleus of the aroyl group or can be present in an aromatic nucleus, which is linked to the aromatic nucleus of the aroyl group by means of a bivalent radical.
  • Suitable color couplers for yellow according to the present invention are color couplers in which at least one sulphonic acid group is implanted directly in the aromatic nucleus of the aroyl group, and which comply with the following general formula:
  • R represents a sulphonic acid group or its salt form
  • R represents hydrogen, halogen, alkoxy, a sulphonic acid group or its salt form, or a group rendering fast to diffusion such as a n-hexadecyloxy group,
  • R represents hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, preferably a group rendering fast to diffusion such as i.e. the group XR, in which X represents a chemical bond, oxygen or sulphur and R an acyclic aliphatic hydrocarbon rest with 5 to 20 carbon atoms,
  • R represents hydrogen, alkyl, substituted alkyl, aryl, a substituted aryl radical with substituents such as alkoxy, halogen, alkylsulphonyl, a group rendering fast to diffusion such as a n-hexadecyloxy group, a n-hexadecylmercapto group or a pentadecyl group, and
  • R and R together may represent the atoms necessary for completing an aromatic ring system, which is either or not further substituted.
  • Suitable color couplers for yellow according to the present invention are color couplers, in which at least one sulphonic acid group in the aroyl part of the molecule is implanted in an aromatic nucleus linked to the aromatic nucleus of the aroyl group by means of a bivalent radical, and which comply with the following general Formula II F-Ra wherein R R and R have the same significance as given in Formula I,
  • R' represents an either or not further substituted sulphonated aromatic radical such as e.g. a sulphonated phenyl group, and
  • Y represents a bivalent radical such as a CONH- group, a SO NH group, or a NHCONH group.
  • R R or R may contain a group rendering fast to diffusion.
  • 4-palmitoyl anisol is prepared by Friedel-Crafts acylation with palmitoyl chloride as described in F. Kralft, Ber. 19 (1886) 2983. After recrystallisation from ethanol 21 white crystalline product is obtained. Melting point: 70 C.
  • 4-(a-bromopalmitoyl)-anisol is obtained in the form of white crystalline leaflets after recrystallisation from ethanol. Melting point: 79-80 C.
  • the base is set free from the resulting aminothiazole hydrobromide by treatment with ammonium hydroxide. After pouring out in water, the resulting precipitate is dried and recrystallised from n-hexane.
  • the 2-amino-4-(a-carbethoxyheptadecyl)-thiazole is obtained in the form of white fine crystal needles. Melting point: C.
  • Col. 6 refers to the number of the structural formula of the prepared color coupler for yellow
  • col. 7 indicates the absorption maximum of the azomethine dye obtained when developing with N-diethyl-p phenylene diamine.
  • Z represents a COCl group or a NCO group
  • W stands for a C( group or a -NHCO- group.
  • reaction step (b') The resulting nitro derivative is then converted into the amine by hydrogenation in the presence of Raney nickel as a catalyst (reaction step (b')).
  • the reduction of hydrogen is consumed, the catalyst is filtered off. On cooling a precipitate is formed in the filtrate. This pre- 0 cipitate is collected and washed with dichloroethane.
  • a yellow filter layer generally comprising colloidal silver dispersed in gelatin is provided usually between (C) Alkaline hydrolysis to sulphonic acid derivatives.- Reaction step (d) The alkaline hydrolysis of the sulphonyl fluoride deriv' the silver halide emulsion layer containing a color couatives P p according reaction p is Carried pler for yellow and the green-sensitised silver halide out as stated under 2(0). The results of specific alkaline 0 emulsion layer,
  • X CO Ethylene glycol mono- 11 465 methyl ether/water.
  • NHCO- do 12 460 The color couplers need not necessarily be separated yellow according to the present invention may be applied in the form of sulphonic acid derivatives before their adin so-called droplet emulsions (cf. US. patent specificadition to the silver halide emulsion. The sulphonic acid tion 2,304,940). derivatives formed in situ from the sulphonyl fluoride For the production of photographic color images acderiva-tives by dissolving the latter derivatives in alkali cording to the present invention an exposed silver halide may be added as such to the emulsion.
  • Preferably 1 mole emulsion layer is developed with an aromatic primary of sulphonyl fluoride derivative is dissolved therefor in amino developing substance in the presence of a color an aqueous solution of 3 mole of sodium hydroxide and coupler for yellow according to the present invention.
  • the resulting clear solution methine dyes can be utilised as developers.
  • Aromatic iS ⁇ added in the form Of a 5 f0 10% aqueous solution l0 primary amino compounds such as p-phenylene diamine the silver halide emulsion.
  • N-diethyl-p-phenylene diamine During the preparation of the lightsensitive color ma- N,N di th l-N'-sul hometh l- -phenylen diamine and terial the non-migratory color couplers for yellow accord- N,N-diethy1-N'-carboxymethyl-p-phenylene diamine are ing to the above-mentioned general formulae are mixed commonly d,
  • the silver halide emulsion contains the i h 1 d i ual Colloids such as gelatin, P y y 31001101),
  • the dyes formed on color development show good lodion or other suitable natural or synthetic colloids.
  • Such photographic multilayer color humidity and heat f dyes f r d on 1 developmaterial usually consists in the given sequence of a ment by reaction of the resulting oxidation product of port, a red-sensitised silver halide emusion layer with a N-dithy1-p-phenylcne diamine with color Couplers color coupler for cyan, a green-sensitised silver halide cording to the present invention and of a color coupler emulsion layer with a color coupler for magenta and described in the British patent specification 873,125.
  • a color coupler for yellow which is a 2-(aroylacetamido)-thiazole, wherein at least one sulfonic acid group is present in the aroyl part of the molecule.
  • Photographic multilayer color material comprising three silver halide emulsion layers which have different optical sensitivities, and containing in nonmigratory form in a member selected from the blue-sensitive silver halide emulsion layer and a non-light-sensitive water-permeable colloid layer adjacent thereto a color coupler for yellow which is a 2-(aroylacetamido)-thiazole wherein at least one sulfonic acid group is present in the aroyl part of the molecule.
  • the acid form as well as the salt form of this group or substituent are meant and that whenever the color couplers are used in the salt form they preferably contain an alkali metal cation, an ammonium group or an amine salt group as a cation.
  • Photographic material comprising a silver halide emulsion layer and a color coupler for yellow which is a 2-(aroylacetamido)-thiazole wherein at least one sulfonic acid group is present in the aroyl part of the molecule.
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • R and R together may also represent the atoms necessary for completing an aromatic ring system.
  • Photographic multi-layer color material containing in non-migratory form in a member selected from the group consisting of a light-sensitive silver halide emulsion layer and a non-light-sensitive water-permeable colloid layer adjacent to said light-sensitive silver halide emulsion layer a color coupler for yellow having the general formula:
  • R represents a member selected from the group consisting of a hydrogen atom, a halogen atom, a methoxy group, a sulfonic acid group, a sulfonic acid salt group, and a group rendering fast to diffusion,
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • Y represent a bivalent radical
  • R' represents a sulphonated aromatic radical
  • Photographic multi-layer color material comprising three silver halide emulsion layers Which have different optical sensitivities, and containing in non-migratory form in a member selected from the blue-sensitive silver halide emulsion layer and a non-light-sensitive water-permeable colloid layer adjacent thereto a color coupler for yellow having the general formula:
  • R represents a member selected from the group consisting of a sulfonic acid group and a salt form thereof
  • R represents a member selected from the group consisting of a hydrogen atom, a halogen atom, a methoxy group, a sulfonic acid group, a sulfonic acid salt group, and a group rendering fast to diffusion,
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • Photographic m-ulti-layer color mate-rial comprising three silver halide emulsion layers which have different optical sensitivities, and containing in non-migratory form in a member selected from the blue-sensitive silver halide emulsion layer and a non-light-sensitive water-permeable colloid layer adjacent thereto a color coupler for yellow having the general formula:
  • R represents a member selected from the group consisting of a hydrogen atom, a halogen atom, a methoxy group, a sulfonic acid group, a sulfonic acid salt group, and a group rendering fast to diffusion,
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, and a group rendering fast to diffusion
  • Y represents a bivalent radical
  • R represents a sulphonated aromatic radical

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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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US381260A 1963-07-09 1964-07-08 Multilayer silver halide elements containing thiazole color couplers for yellow Expired - Lifetime US3393041A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3645742A (en) * 1968-01-05 1972-02-29 Agfa Gevaert Nv Color photography

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863874A (en) * 1955-05-26 1958-12-09 Goodrich Co B F Process of preparing 2-aminothiazoles
US2895825A (en) * 1954-03-18 1959-07-21 Agfa Ag Production of photographic colour images with heterocyclic developers
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
US3008827A (en) * 1957-06-19 1961-11-14 Gevaert Photo Prod Nv Production of colored photographic images
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development
US3124588A (en) * 1964-03-10 Z-acylamtoo-s-nitrothiazole

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3124588A (en) * 1964-03-10 Z-acylamtoo-s-nitrothiazole
US2895825A (en) * 1954-03-18 1959-07-21 Agfa Ag Production of photographic colour images with heterocyclic developers
US2863874A (en) * 1955-05-26 1958-12-09 Goodrich Co B F Process of preparing 2-aminothiazoles
US2933391A (en) * 1956-09-06 1960-04-19 Eastman Kodak Co Photographic emulsions containing 5-pyrazolone coupler compounds
US3008827A (en) * 1957-06-19 1961-11-14 Gevaert Photo Prod Nv Production of colored photographic images
US2983608A (en) * 1958-10-06 1961-05-09 Eastman Kodak Co Yellow-colored magenta-forming couplers
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3645742A (en) * 1968-01-05 1972-02-29 Agfa Gevaert Nv Color photography

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GB1075084A (en) 1967-07-12
DE1213739B (de) 1966-03-31
BE634670A (en))
CH446059A (fr) 1967-10-31

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