US3849140A - Diffusion-resistant dispersible yellow couplers for the production of photographic color images - Google Patents

Diffusion-resistant dispersible yellow couplers for the production of photographic color images Download PDF

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Publication number
US3849140A
US3849140A US00236972A US23697272A US3849140A US 3849140 A US3849140 A US 3849140A US 00236972 A US00236972 A US 00236972A US 23697272 A US23697272 A US 23697272A US 3849140 A US3849140 A US 3849140A
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Prior art keywords
coupler
couplers
diffusion
resistant
production
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Expired - Lifetime
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US00236972A
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English (en)
Inventor
K Kuffner
H Glockner
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Agfa Gevaert AG
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Agfa Gevaert AG
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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

Definitions

  • This invention relates to color couplers which react with suitable developer substances of the p-phcnylene diamine type to form yellow dyes according to the principle of chromogenic development.
  • These color coupiers are preferably used in the blue-sensitive component layer of multiple-layer color photographic materials containing silver halide as the photosensitive substance.
  • derivatives of benzylacetanilide are mainly used as color couplers for the aforementioned purpose.
  • the properties of the couplers, and of the dyes formed from them, can be influenced within wide limits by suitable substituents at various positions in the molecule.
  • the introduction of relatively long hydrocarbon radicals makes the compounds resistant to diffusion, so that they can be embedded in the blue-sensitive component layer of the multiple-layer colour material.
  • the effect of introducing a sulfo group or carboxyl group into the molecule is that the colour couplers can be added to the silver halide emulsion in the form of water-soluble alkali metal salts.
  • the present invention relates to diffusion-resistant water-insoluble yellow couplers which are used in dispersed form.
  • couplers such as these are extremely varied, the following being mentioned by way of example: high solubility in certain organic solvents and a relatively low melting point with a consequent high dispersibility in water or gelatin solution; high resistance to diffusion, stability of the coupler against climatic influences during storage ofthe finished color materials; limited influence upon the photographic properties of the silver halide; high reactivity during color development; favourable spectral properties of the developed dye; and resistance of the image dye to light and climatic influences.
  • the coupler should be easy to prepare, thus minimising production costs.
  • R represents a diffusion-inhibiting radical in the form of a linear or branched hydrocarbon chain having at least carbon atoms
  • X represents hydrogen or a radical which can be split off during colour coupling, mostly chlorine
  • R represents halogen, cyano, R 0R CF COOR CONH COM- R CON(R S0 R SO NH SOzNHRg, SO2N(R3)2, 0r
  • radicals R if two or more radicals R are present, they can be the same or different;
  • R represents alkyl having l to 4 carbon atoms or aryl, and iftwo groups R occur in the same radical, they can be the same or different;
  • n 1, 2 or 3.
  • couplers of this kind have the formula (II):
  • Couplers used according to the invention with couplers in which an alkoxy group is situated in the para-position of the benzoyl radical, is of particular significance.
  • This para-alkoxy substitution leads to extremely active couplers which have, however, disadvantages in comparison with the couplers used according to the invention, including longer-wave absorption of the developed dyes and lower solubility, for example in ethyl acetate.
  • the melting points of couplers having a long-chain alkoxy substituent in the para-position are from 10 to 40C higher than the melting points of the corresponding couplers with the long-chain alkoxy substituents in the ortho-position.
  • the process for producing the new couplers is known in principle and comprises reacting suitably substituted aniline derivatives with long-chain o-alkoxybenzoylacctic esters. It is worth noting that these esters can be produced relatively easily compared with o-methoxy-benzoylacetic esters which are much more difficult to obtain.
  • the coupler obtained can be subsequently converted into a 2-equivalent coupler, also by known methods.
  • the new couplers can readily be introduced into a silver halide emulsion.
  • the dispersions are prepared by known methods. The most common method is to prepare a solution in water or gelatin solution with the assistance of a suitable wetting agent, and then to evaporate off the solvent. If necessary, a so-called oil former can be added in order to prevent crystallisation. There is, however, generally no need to do this with the couplers according to the invention, because of their particularly high dispersibility. The disadvantages of using oil formers are known.
  • the new yellow couplers react really well with the oxidation products of all conventional developers of the p-phenylene diamine type, for example N,N-diethyl-p-phenylene diamine (CD 1 N,N-diethyl- 3-methyl-p-phenylene diamine (CD 2), 4-amino-3 lengths. Secondary absorption in the green region of the spectrum is minimal.
  • the properties of the 2-equivalent couplers used ac-' cording to the invention, especially with chlorine as the separa bleradical, are particularly remarkable. During color development, these couplers cause little or no color fogging, a property which distinguishes them with advantage from most of the 2-equivalent couplers which have been described.
  • the components according to the invention can be used both in the negativepositive process and also in the reversal process. Both film and paper can be used as layer substrate for the layers.
  • Coupler 13 a Methyl Z-tetradecyloxybenzoate 23 g of sodium metal were dissolved in 500 ml of ethylene glycol monomethylether, followed by the addition of a solution of 125 g of methyl salicylate in 400 ml of ethylene glycol monomethylether. The resulting mixture was then brought to boiling while stirring, followed by the dropwise addition of 277 g of tetradecyl bromide over a period of 3 hours. The mixture was then boiled for another hour, after which it was left to cool.
  • Coupler 17 2-tetradecyloxybenzoyl-2-methoxy-acetanilide This coupler was prepared in accordance with Specification 1f, except that 13.5 g of o-anisidine were used instead of the 4-amino toluene.
  • Coupler 18 2-tetradecyloxybenzoyl-2'-methoxy-chloroacetanilide This coupler was prepared in accordance with Specification 2, except that, instead of coupler 13, 24.2 g of. coupler 17 were reacted with 6.75 g of sulfuryl chloride.
  • Coupler l9 Z-tetradecyloxybenzoyl-Z-methoxy-fluoroacetanilide A three-necked flask equipped with stirring mechanism, thermometer and gas-inlet pipe, was filled with 300 ml of methanol. The methanol was cooled to -C with acetone/dry ice. Perchloryl fluoride was then introduced until the methanol contained 5.5 g of perchloryl fluoride.
  • Coupler 41 2-tetradecyloxybenzoyl-2'-chloro-5'-N-methyl myl-acetanilide This coupler was prepared in accordance with Specification 1f, except that 22 g of 2-chloro-5-N-methylsulsulfa- Y ield: 40 g M.p. 92C;
  • Coupler 42 Z-tetradecyloxybenzoyl-Z'-chloro-5 '-N-methylsulfamylchloroacetanilide This coupler was prepared in accordance with Specification 2, except that, instead of coupler 13, 29 g of coupler 41 were reacted with 6.75 g of sulfuryl chloride. Yield: 23.4 g M.p. 84 86C.
  • Coupler 48 2-tetradecyloxybenzoyl-4-methylsulfonyl-acetanilide This coupler was prepared in accordance with Specification 1f, except that 17.1 g of 4-methylsulfonylaniline were used instead of 4-amino-toluene. Yield: 35 g M.p. 79 80C. 19. Coupler 49 into ml of 7.5% by weight gelatin solution containing 0.25 g of sodium dodecylbenzene sulfonate. Dispersion time was 2 minutes, a Kotthoff mixing siren being used for dispersion. The ethyl acetate was evaporated off on a water bath. This dispersion could be stored for several days without change, either in liquid form or in solid form. b. Photographic application.
  • the above dispersion was added to 50 g ofa negative emulsion.
  • the silver content, expressed as AgNO was 49 m ftzll winsssditia Qt s usual s s d tives, the emulsion was cast onto a layersubstrate and dried. Thereafter, samples were exposed under a step wedge (blue filter) both fresh and after cold storage (for 7 days at -C). The samples were subjected to a negative development process (developer substances diethyl-p-phenylene diamine). The following measurements were obtained:
  • EXAMPLE 2 a A dispersion was prepared from 2.06 g of coupler 18 in the manner described in Example la.
  • This coupler had the tetradecyloxy group in the para.
  • X represents chlorine
  • R represents halogen, cyano, R OR -COOR -CONH CONHR CON(R SO R SO NH SO NHR -SO N(R or SO F, and if two or more groups R are present, they can be the same or different;
  • R represents alkyl having 1 to 4 carbon atoms or aryl, and if two groups R occur in the same radical, they can be the same or different;
  • n 1, 2 or 3.
  • a color photographic material as claimed in claim 1 wherein the yellow coupler has the formula R 6R1 (in 2) l in which.
  • R R X and n have the meanings given in claim 1.
  • Color photographic material as claimed in claim 1 I which has a plurality of emulsion layers, the yellow coupler being present in the blue-sensitive layer.
  • a color photographic material which comprises at least

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US00236972A 1971-03-25 1972-03-22 Diffusion-resistant dispersible yellow couplers for the production of photographic color images Expired - Lifetime US3849140A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2114577A DE2114577C3 (de) 1971-03-25 1971-03-25 Farbfotografisches Aufzeichnungsmaterial

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US3849140A true US3849140A (en) 1974-11-19

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US00236972A Expired - Lifetime US3849140A (en) 1971-03-25 1972-03-22 Diffusion-resistant dispersible yellow couplers for the production of photographic color images

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US (1) US3849140A (OSRAM)
BE (1) BE780672A (OSRAM)
DE (1) DE2114577C3 (OSRAM)
FR (1) FR2130713B1 (OSRAM)
GB (1) GB1351395A (OSRAM)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529691A (en) * 1983-04-15 1985-07-16 Agfa-Gevaert Ag Color photographic recording material containing color couplers
US4587207A (en) * 1983-09-27 1986-05-06 Fuji Photo Film Co., Ltd. Color image-forming process
WO1998022822A1 (en) * 1996-11-21 1998-05-28 Applied Imaging Corporation Photographic color couplers used as cytochemical contrast markers

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH627562A5 (de) 1977-04-29 1982-01-15 Ciba Geigy Ag Farbphotographisches material.
FR2405504A1 (fr) * 1977-10-07 1979-05-04 Agfa Gevaert Copulants chromogenes pour le jaune pour la photographie aux halogenures d'argent
JPS557702A (en) * 1978-06-01 1980-01-19 Konishiroku Photo Ind Co Ltd Silver halide color photographic material

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409439A (en) * 1964-02-01 1968-11-05 Fuji Photo Film Co Ltd Color photographic materials
US3725072A (en) * 1969-10-17 1973-04-03 Fuji Photo Film Co Ltd Color photographic light-sensitive materials containing a novel yellow-forming coupler

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2407210A (en) * 1944-04-14 1946-09-03 Eastman Kodak Co Color couplers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409439A (en) * 1964-02-01 1968-11-05 Fuji Photo Film Co Ltd Color photographic materials
US3725072A (en) * 1969-10-17 1973-04-03 Fuji Photo Film Co Ltd Color photographic light-sensitive materials containing a novel yellow-forming coupler

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529691A (en) * 1983-04-15 1985-07-16 Agfa-Gevaert Ag Color photographic recording material containing color couplers
US4587207A (en) * 1983-09-27 1986-05-06 Fuji Photo Film Co., Ltd. Color image-forming process
WO1998022822A1 (en) * 1996-11-21 1998-05-28 Applied Imaging Corporation Photographic color couplers used as cytochemical contrast markers

Also Published As

Publication number Publication date
DE2114577C3 (de) 1981-12-03
FR2130713B1 (OSRAM) 1977-04-01
FR2130713A1 (OSRAM) 1972-11-03
DE2114577B2 (de) 1981-04-09
BE780672A (nl) 1972-09-15
GB1351395A (en) 1974-04-24
DE2114577A1 (de) 1972-10-05

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