US3469986A - Silver halide emulsions containing magenta - colored cyan - forming couplers - Google Patents

Silver halide emulsions containing magenta - colored cyan - forming couplers Download PDF

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Publication number
US3469986A
US3469986A US522556A US3469986DA US3469986A US 3469986 A US3469986 A US 3469986A US 522556 A US522556 A US 522556A US 3469986D A US3469986D A US 3469986DA US 3469986 A US3469986 A US 3469986A
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Prior art keywords
coupler
group
color
absorption
couplers
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US522556A
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English (en)
Inventor
Makoto Yoshida
Keisuke Shiba
Akio Okumura
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Fujifilm Holdings Corp
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Fuji Photo Film Co 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
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore

Definitions

  • This invention relates to color photography and particularly to colored cyan couplers for use in photographic processes.
  • cyan couplers used in the color image formation of color photography are l-naphthol-Z-carboxylic acid derivatives or aminophenol derivatives.
  • a long chain alkyl radical is introduced into the molecule to prevent the difiusion of the added coupler from the layer in which it is added to another layer.
  • more than one carboxylic or sulfonic acid group, as alkali solubilizing groups are introduced to disperse the coupler homogeneously in a photographic emulsion layer.
  • the coupler is often provided with oleophilic proper-ties in order to dissolve it in an organic solvent, called a coupler solvent hereinafter.
  • the cyan image obtained by coupling of these couplers with an oxidized color developer have undesirable absorption in the blue and more especially green region.
  • R represents alkyl radical containing more than 10 carbon atoms
  • Y is a member selected from the group consisting of -COOM, 40 M and a carboalkoxy group
  • n is 1 or 2, show good masking effect.
  • an object of the present invention to provide alkali-soluble, magenta-colored, cyan couplers which show little color change depending on the pH value of the color processing solution.
  • a further object is to provide magenta-colored, cyan couplerswhich show no. desensitization and little occurrence of fog.
  • R represents an alkyl group having more than 10 carbon atoms
  • M represents hydrogen, an alkali metal
  • the coupler of this invention has good solubility in aqueous alkali solutions because the anilide nucleus at the -2-position of naphthol nucleus contains a sulfo group as shifts the maximum wave length of spectral absorption 'in a film to a longer wave length, whereby the spectrum absorption in the film is improved to a great extent.
  • an alkoxy group containing more than carbon atoms together with a sulfo group is introduced into the 0-position of the amido group in the anilide nucleus at the 2-position of the naphthol nucleus. It is a feature of the chemical structure of the coupler of this invention that it is-provided with the property of being diffusion-fast by virtue of a long chain alkoxy group without loss of its excellent color property.
  • the coupler of this invention is characterized by containing a lit-naphthylazo group substituted by a sulfo group at 4-position of naphthol nucleus.
  • the colored coupler which contains the naphthylazo group demonstrates larger bathochromic shifts than the coupler containing a substituted or unsubstituted phenylazo group.
  • a colored coupler containing unsubstituted naphthylazo group however, has undesirably high blue absorption and also red absorption. This undesirable tendency is less in the fi-naphthylazo group than in tat-naphthylazo group.
  • A contains a phenylazo group, B tat-naphthylazo, and C B-naphthylazo group.
  • the introduction of the sulfo group into ,B-naphthylazo group not only improves greatly the solubility in aqueous alkali solution but, more significantly, reduces the undesirable blue and red absorption to a great extent and remarkably improves the spectral absorption in the film. That is, the maximum absorption wave length in the film is about 20 m longer compared with the maximum absorption wave length in aqueous solution, and the blue absorption is reduced to provide a very desirable magenta, without red absorption (see FIG. 2). Additionally, the change of color caused by the pH-value of the processing solution is reduced.
  • couplers which may be used according to our invention.
  • couplers of this invention will not be restricted only thereto.
  • couplers of this invention demonstrate excellent properties, using the following control couplers, i.e., A containing a phenylazo group, B containing an a-naphthylazo group and C containing a B-naphthylazo group.
  • Compound (I) and comparative coupler A, B and C each is weighed in a given amount, dissolved in a small amount of l N caustic soda solution, diluted with a phosphate butter solution of pH 7.0 to prepare a solution of 4X 10* mols at a pH-value of 7.0 respectively and their spectral absorption curves are measured.
  • the curve in which the maximum absorption density attains 1.0 is shown in FIG. 1.
  • the spectral absorption curve of compound (I) in a film obtained in Example 1 (I)/F, the spectral absorption curve of compound (I) in said aqueous solution (I)/W and the spectral absorption curve of compound (A) in a film (A)F are shown graphically in FIG. 2, in which the maximum absorption density makes to 1.0.
  • the couplers of this invention were prepared as follows: Compound of formula I.l-hydroxy-4-(S-sulfo-fl-naphthylazo)-2-(2-octadecyloxy-5-sulfo)naphthanilide 7 g. of 2-naphthylamine-8-sulfonic acid and 1.5 g. of
  • caustic soda were dissolved in 50 ml. of water. 3 g. of
  • the yield was 15 g. (71 and the melting point was above 280 C.
  • the yield was 12 g. (611%) and the melting point was above 280 C.
  • Example 1 N,N-diethyl-p-aminoanilinesulfate, g. 2.0 Anhydrous sodium sulfite, g 20.0 Sodium carbonate (monohydrate) 50.0 Hydroxylamine hydrochloride 1.5 Potassium bromide 1.0
  • Potassium ferricynanide g 100 Potassium bromide 20 Water, up to 1,000 ml. (pH- 6.9 0.3).
  • the maximum spectral absorption wave length of positive image obtained was 530 mp showing a desirable magenta color.
  • the color of the positive image obtained was almost unchanged even by passing it through a stabilizing bath varying the pH-value from 4 to 11 (see Fig. 2).
  • Example 2 An equivalent amount of 1.5x 10 mols of N-n-octadecyl-l-hydroxy-4-sulfo 2 naphthamide sodium salt in aqueous 5% caustic soda solution was added to g. of sensitive emulsion containing panchromatic sensitizer. An equivalent amount of 1.0x 10 mols of said salt and an equivalent amount of 0.5x 10* mols of compound (I), (IV) and (V) in aqueous 5% caustic soda solution were respectively added to said emulsion in the same manner as in Example 1 to obtain red sensitive materials.
  • FIG. 3 The characteristic curve in which the undesirable green absorption is masked is shown in FIG. 3.
  • the solid line shows the use of compound (I) in admixture with N-n-octadecyl-1-hydroxy-4-sulfo-Z-naphthamide sodium salt and the dotted line shows the use of N-n-octadecyl-1-hydroxy-4-sulfo-Z-naphthamide sodium salt alone.
  • 1 is the cyan density on using a red filter and 2 that on using a green filter. From the fact mentioned above, it will be understood that the coupler of this invention has no desensitization and little occurence of fog so that it has a suitable spectral absorption characteristic.
  • a color photographic silver halide emulsion containing a color coupler having the formula:
  • R represents an alkyl group having more than 10 carbon atoms
  • M represents a member selected from the group consisting of hydrogen, an alkali metal, an ammonium group, and H.NH ,(R") where p is an integer selected from the group 0 to 3, q is an integer selected from the group 0 to 3 inclusive, p-
  • -q 3, and R" is a lower alkyl group; and n is an integer selected from the group 1 to 2 inclusive.
  • the color photographic emulsion of claim 1 wherein 6.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US522556A 1965-01-23 1966-01-24 Silver halide emulsions containing magenta - colored cyan - forming couplers Expired - Lifetime US3469986A (en)

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US (1) US3469986A (enrdf_load_stackoverflow)
BE (1) BE675372A (enrdf_load_stackoverflow)
CH (1) CH466037A (enrdf_load_stackoverflow)
DE (1) DE1547830A1 (enrdf_load_stackoverflow)
FR (1) FR1524044A (enrdf_load_stackoverflow)
GB (1) GB1091984A (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4957853A (en) * 1985-10-08 1990-09-18 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material containing cyan coupler and method for use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1597510A1 (de) * 1967-12-21 1970-06-25 Agfa Gevaert Ag Verbessertes farbphotographisches Material

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2688539A (en) * 1951-11-08 1954-09-07 Gen Aniline & Film Corp Integral masking of photographic silver halide emulsions arranged in contiguous layers and containing colorless color formers and azo substituted coupling components
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2688539A (en) * 1951-11-08 1954-09-07 Gen Aniline & Film Corp Integral masking of photographic silver halide emulsions arranged in contiguous layers and containing colorless color formers and azo substituted coupling components
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4957853A (en) * 1985-10-08 1990-09-18 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material containing cyan coupler and method for use thereof

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Publication number Publication date
GB1091984A (en) 1967-11-22
CH466037A (de) 1968-11-30
BE675372A (enrdf_load_stackoverflow) 1966-05-16
FR1524044A (fr) 1968-05-10
DE1547830A1 (de) 1970-02-19

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