US3685995A - Yellow-forming coupler compounds and color photographic elements containing same - Google Patents

Yellow-forming coupler compounds and color photographic elements containing same Download PDF

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US3685995A
US3685995A US26350A US3685995DA US3685995A US 3685995 A US3685995 A US 3685995A US 26350 A US26350 A US 26350A US 3685995D A US3685995D A US 3685995DA US 3685995 A US3685995 A US 3685995A
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group
coupler
yellow
carbon atoms
anilide
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Makoto Yoshida
Momotoshi Tsuda
Yasushi Oishi
Kiyoshi Nakazyo
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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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/362—Benzoyl-acetanilide couplers

Definitions

  • WAVE LENGTH (MILLIMICRONS) INVENTORS MAKOTO YOSHIDA d a V MOMOTOSHI TSUDA 460 560 660 YASUSH! OISHI WAVE LENGTH (MILLIMICRONS) K'YOSHI NAKAZYO g m ifm M, BY 71% 4 Mar aK.
  • the present invention relates to a color photographic light-sensitive element containing a novel yellow-forming coupler.
  • couplers which form cyan, magenta and yellow dyes respectively by the coupling thereof with the oxidation product of a developing agent, a N,N-di-substituted paraphenylenediamine compound, formed simultaneously when silver halide emulsion grains are developed by said developing agent, are generally employed.
  • the yellow dye image formed in a color photography by a subtractive color process absorbs usually blue light of a wavelength range of from about 400 millimicrons to about 500 millimicrons.
  • the image has a strong absorption in the above-mentioned range of wave lengths but has less absorption in the green range and the red range having wave lengths longer than 500 millimicrons.
  • the couplers In the case where the couplers are incorporated in silver halide emulsions having corresponding spectral sensitivities repsectively during the production of multiplelayer type color photographic light-sensitive elements, the couplers must possess diffusion resistance or ballasting property for preventing the migration of each of the couplers in a silver halide emulsion layer into another emulsion layer, whereby the coupler is mixed with other couplers to degrade the color reproducing property.
  • ballasted coupler For incorporating such a ballasted coupler in a photographic emulsion layer, two methods are known. These methods are an aqueous solution method and an oil solution method. In the former method, the ballasted coupler has a water-solubilizing group and is incorporated in the silver halide emulsion as an alkaline solution thereof in water, whereas in the latter method the coupler is dissolved in an organic solvent and the resultant solution is added to a silver halide emulsion as an emulsified dispersion of the fine colloidal particles thereof in an aqueous medium.
  • the yellow-forming coupler incorporated in a photographic emulsion layer by the aforesaid oil-solution method can give dye images with better spectral absorption characteristics and higher stability to moisture than those of the yellow coupler incorporated by the water-solution method.
  • the coupler employed in the above-mentioned oil-solution method must be readily soluble in an organic solvent for preparing the dispersion and to be less crystallizable in the solvent.
  • the coupler incorporated in the silver halide emulsion layer have a coupling reactivity of a definite level with the oxidation product of a N,N-di-substituted para-phenylene diamine developing agent.
  • a conventional yellow coupler incorporated in a photographic emulsion layer by the oil-solution method generally shows a low coupling reactivity.
  • color images obtained from conventional yellow-forming couplers heretofore known generally have a tendency to fade when they are exposed to intense light for a long period of time. This has been a big hindrance in storing the color photographs for a long period of time.
  • the yellow-forming couplers to be employed in the oil-solution system desirably should possess sufficient coupling reactivity, should have less green absorption, and should give rise to dye images which are fast to light.
  • Yellow-forming couplers have been investigated and as the result thereof, it has been discovered also that compounds represented by the following general Formula I, shown below, have particularly excellent properties as yellow-forming couplers suitable for the oilsolution system and having suflicient diffusion resistance ITIHCOR l X Formula I wherein X represents a halogen atom, a lower alkoxyl group, a dialkylamino group or an aryloxy group; Y represents a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, an alkyl group having less than 8 carbon atoms, an alkoxyl group, an aryloxy group, an acyl group, a carbamyl group, an acylamino group, a sulfoamino group, a sulfoamoyl group, a carboalkoxyl group, or an amino group; R represents an alkyl group having 1 to carbon atoms; and C
  • the substituent represented by Y is introduced to one of the 3-, 4- and 5-positions of the anilide ring. That is, a compound having group Y at the 6-position of the anilide ring has an extremely low coupling reactivity and provides a yollow image having a strong green absorption, and hence is unsuitable for the purposes of the present invention.
  • acyl group represented by COR' in the general Formula I has less than 9 carbon atoms, sufficient oilsolubility and diffusion resistance to the coupler does not result, while if the number of carbon atoms in the acyl group is larger than 28, the molecular weight of the coupler is so much increased that the blue absorption per unit weight or volume of the yellow dye formed is reduced, the solubility of the coupler itself is reduced due to the increased dispersing power based on the acyl group, and also the thickness of the photographic emulsion layer containing the coupler must be increased to provide a definite blue density to the photographic emulsion layer.
  • acyl group represented by -COR' in the general Formula I a substituted or unsubstituted aliphatic acyl group or the following groups are particularly suitable:
  • R represents an alkyl group having 5 to 18 carbon atoms
  • R and R each represents an alkyl group having less than 9 carbon atoms
  • R represents a hydrogen atom or an alkyl group having less than 3 carbon atoms
  • n is a positive integer of 2 to 5.
  • coupler can have sufficient oil solubility for being dispersed in the oil-solution system.
  • novel yellow-forming couplers of the present invention provide color images which are extremely stable when exposed to intense light. Moreover, the fading tendency in light of the color image obtained with the novel yellow-forming coupler of the present invention can be further reduced by providing an ultra violet absorption layer capable of absorbing selectively light, having wave lengths shorter than about 400 millimicrons, on the surface of the silver halide emulsion layer having the yellow image formed by the coupling of said coupler, on the side exposed to light. Suitable ultraviolet absorption layers are disclosed in Japanese patent application No. 19,299/1968.
  • the yellow coupler obtained from the novel yellowforming coupler of the present invention is resistant to the actions of heat and moisture.
  • the color photograph obtained from the color photographic light-sensitive element of the present invention can be stored stably for a long period of time even under severe conditions with less discoloring and fading.
  • the yellow-forming coupler of this invention represented by the general Formula I can give a yellow image having spectral absorption characteristics suitable for the requirements of color reproduction in substractive color process. This advantage will be explained below in comparison with known yellow-forming coupler represented by the following general Formula II ITTHC OR wherein X and COR have the same meaning as described in regard to the general Formula I.
  • FIG. 1 of the accompanying drawings the spectral absorption curve (Curve 1) of an ethyl acetate solution of the yellow dye prepared by the oxidation coupling of the novel coupler having the general Formula I, 3-[04-(2', 4'-di-tert amylphenoxy)butylamido]-4-me.thoxybenzoylaceto-2-chloroanilide, and a developing agent, 4-amino-3- methyl-N,N-diethylaniline, and the spectral absorption curve (Curve 2) of an ethyl acetate solution of the yellow dye obtained by the oxidation coupling of a known coupler having the general Formula II, 3-(2',4'-di-tertamylphenoxy)acetoamido benzoylaceto-Z-chloroanilide, and the aforesaid developing agent are shown.
  • the yellow-forming coupler of the present invention provides a clear yellow dye having a spectral absorption curve sharper on the long wave length side than the absorption of the conventional coupler and having less green absorption of wave lengths longer than 500 millimicrons than the absorption of the conventional coupler.
  • the organic solvent used for dissolving the coupler of the present invention in preparing a color photographic light-sensitive element be substantially water-immiscible and have a boiling point higher than C. at normal pressure.
  • Such an organic solvent having a high boiling point and being immiscible with Water not only facilitates the emulsifying disperson of the coupler but also contributes to preventing the crystallization of the coupler, improves the spectral absorption characteristics of the color image, and improves the stability of the color image by staying in the emulsion layer together with the coupler.
  • Suitable organic solvents are carboxylic acid esters, phosphoric acid esters, carboxylic acid amides, ethers, and substituted hydrocarbons.
  • organic solvents are di-nbutyl phthalate, di-iso-octyl azelate, dibutyl sebacate, tricresyl phosphate, N,N-diethyl caprylic amide, butyl-npentadecyl phenyl ether, and chlorinated parafiin.
  • a low boiling solvent or a high boiling water-miscible solvent alone or together with the above-described water-immiscible high boiling solvents.
  • Suitable specific examples of these solvents are propylene carbonate, ethyl acetate, cyclohexanol, tetrahydrofur'an, cyclohexanone, dimethyl formamide, ethylene glycol monomethyl ether, and the like.
  • N,N-disubstituted-para-phenylenediamine derivative is preferred.
  • Specific examples of these derivatives are N,N-dimethyl-p-phenylenediamine,
  • the couplers represented by the general Formula I can be used alone in combinations of two or more such couplers, or together with other conventional yellow-forming couplers. Furthermore, it is sometimes advantageous to use the coupler represented by the general Formula I together with a known yellowforming coupler employed in the water-solution system.
  • the present invention can be applied to various kinds of light-sensitive elements with good results.
  • the invention can be applied to color photographic printing papers, color photographic positive films, color photographic negative films and color photographic reversal Compound A lTII-ICOCHQO- Compound B (32115 llVHC CH0- Compound C NHCOCHzOHzN CJHQ NHCOCHECO OCH3 OCHa Compound D IT HC O CHO- C H (tert) Nrr0ocH2c0--oom 0511mm) (LCHs Compound E IIIHCO CH2O 1 o1 NHCOCH2COOCH; 015mm I Cl
  • Compound G (3 015 31 (C H gNOgS NHCOOH'JCHQN C4H9 NHCOCH2CO- -OCH3 Compound H (0
  • PREPARATION EXAMPLE 3 (3a) Preparation of 4-methoxy-3-nitrobenzoylaceto-(2-methoxy)anilide The same procedure as used in Preparation Example (l-a) was followed by using 62 g. of o-anisidine instead of o-chloraniline to provide 159 g. (92% yield) of the above-mentioned anilide having a melting point of 168- 169 C.
  • PREPARATION EXAMPLE 4 (4-a) Preparation of 4-methoxy-3-nitrohenzoylaceto- (2-chloro-S-tri-fluoromethyl)anilide The same procedure as used in Preparation Example (1a) was followed using 58 g. of 2-chloro-5-fluoromethylaniline instead of o-chloroaniline to provide 166 g. yield) of the aforesaid anilide having a melting point of 168169 C.
  • reaction product solution was poured in two liters of ice-cooled water acidified with hydrochloric acid to crystallize the product, which was recovered by filtration, washed with water and recrystallized from methanol to provide 119 g. (53% yield) of the pure crystals of the aforesaid anilide having a melting point of 103-l05 C.
  • PREPARATION EXAMPLE 7 (7-a) Preparation of 4-methoxy-3-nitrobenzoylaceto- (Z-methoxy-5 N,N-diethylaminosulfo) anilide The same procedure as used in Preparation Example (1-a) using 129 g. of 2-methoxy-S-N,N-diethylaminosulfoaniline instead of o-chloroaniline in the example to provide 167 g. (70% yield) of the above anilide having a melting point of 198 C.
  • PREPARATION EXAMPLE 8 (8 a) Preparation of 4-methoxy-3-nitrobenzoylaceto- (Z-methoxy-S-methyl) anilide The same procedure as used in Preparation Example (l-a) was followed byusing 137 g. of 2-methoxy-5- methylaniline instead of o-chloroaniline in the example 11 to provide 168 g. (94% yield) of the aforesaid anilide having a melting point of 202203 C.
  • EXAMPLE 1 A solution prepared by refluxing a mixture of 30 g. of Compound B shown by the aforesaid structural formula, ml. of di-n-butyl phthalate, and 60 ml. of ethyl acetate was added to 600 ml. of an aqueous solution containing 50 g. of gelatin and 2.5 g. of sodium dodecylbenzene sulfonate with stirring and the resultant mixture was passed five times through a colloid mill, whereby the coupler was dispersed by emulsification together with the solvents.
  • the entire amount of the dispersion was added to 1.0 kg. of a silver halide emulsion containing 54 g. of silver iodobromide and 60 g. of gelatin and after adding ml. of an acetone solution of 3 triethylene phosphamide as a hardening agent and adjusting the pH of the emulsion to 6.0, the resultant silver halide emulsion was applied to a triacetyl cellulose film at a dry thickness of 7.0 microns.
  • the light sensitive film thus prepared is designated hereinafter as Film U.
  • composition of the color developer used in the above color development was as follows:
  • the fixing solution and the bleaching solution used above were aqueous solutions, each containing sodium thiosulfate and a ferricyanide, respectively.
  • Films U and V each showed the maximum density of 2.85 and 2.95 respectively to blue light.
  • FIG. 2 of the accompanying drawings The spectral absorption curves of the colored images of these two films obtained by the above photographic procedures are shown in FIG. 2 of the accompanying drawings.
  • the spectral absorption curve of the color image obtained by using Film U shows less absorption in the wave length region longer than 500 millimicrons as compared with the spectral absorption curve of the color image obtained by using Film V (Curve 4). According to the result, Film U gave a less reddish brilliant yellow image as compared with the color image of Film V.
  • the two photographic films thus processed were exposed for 40 hours to light from a xenon arc lamp of 1.5 watts and thereafter were measured on reduction in blue densities, the results of which are shown below:
  • EXAMPLE 2 A mixture of 21 g. of the Coupler F shown before, 20 ml. of di-n-butyl phthalate, and 45 ml. of cyclohexanone was heated to 60 C. to dissolve the coupler and the solution thus prepared was added to 300 ml. of an aqueous solution containing 25 g. of gelatin and 1 g. sodium dodecylbenzene sulfonate, and stirred vigorously, whereby the coupler was dispersed together with the solvents.
  • the entire amount of the dispersion was added to 500 g. of a photographic emulsion containing 45 g. of silver iodobromide and 50 g. of gelatin and after adding to the mixture 30 ml. of a 3% acetone solution of triethylene phosphamide as a hardening agent and adjusting the pH of the mixture to 7.0, the resultant mixture was applied to a triacetyl cellulose film at a dry thickness of 6.0 microns.
  • Example 2 The film was exposed and processed as in Example 1, whereby a yellow image having a high coupling density and an absorption maximum at 456 millimicrons was obtained.
  • the photograph thus processed was stored for 20 days under the conditions of 65 C. in temperature and 75% in relative humidity, substantially no reduction in blue density was observed.
  • EXAMPLE 3 A solution prepared by heating a mixture of 15.5 g. of the Compound K shown above, 8 ml. of di-n-butyl phthalate, and 30 ml. of butyl acetate was added to an aqueous solution containing 10 g. of gelatin and 0.7 g. of sodium dodecylbenzene sulfonate. The mixture was stirred for 15 minutes vigorously in a high speed mixer, whereby the coupler was dispersed finely.
  • the entire amount of the dispersion was mixed with 1 kg. of a blue-sensitive photographic emulsion containing 45 g. of silver chlorobromide and 70 g. of gelatin and, after adding 30 ml. of a 3% acetone solution of triethylene phosphamide as a hardening agent and adjusting the pH thereof to 6.0, the resulting mixture was applied to a triacetyl cellulose film in a dry thickness of 6.5 microns.
  • a rcd-sensitive emulsion containing the cyan-forming coupler b having the structure shown below To the emulsion layer prepared were applied a rcd-sensitive emulsion containing the cyan-forming coupler b having the structure shown below, a green-sensitive emulsion containing the magenta-forming coupler 0 having the structure shown below, and finally a protective layer of gelatin to provide a color photographic light-sensitive element.
  • Coupler b (
  • the color photographic positive film thus prepared was exposed through a color negative and processed as in Example 1 to provide a clear color positive.
  • the yellow image of the color positive showed excellent heat and moisture resistance.
  • EXAMPLE 4 A solution prepared by heating a mixture of 20 g. of the Compound M shown above, 30 ml. of tricresyl phosphate, and 50 ml. of ethyl acetate was mixed with 250 ml. of an aqueous solution containing 1.5 g. of sodium dodecyl sulfate and 20 g. of gelatin and the mixture was stirred vigorously for 30 minutes in a homogenizer, whereby the coupler was finely dispersed together with the solvents.
  • the entire amount of the dispersion was added to 540 .g. of a blue-sensitive photographic emulsion containing 30 g. of silver chlorobromide and 35 g. of gelatin and, after adding thereto 30 ml. of a 3-acetone solution of triethylene phosphamide and 2 g. of polyvinyl pyrrolidone, the resultant mixture was applied to a baryta-coated paper in a dry thickness of 4.5 microns.
  • Color Printing Paper W a color photographic printing paper containing the magenta-forming coupler shown above, a red-sensitive emulsion containing the cyan-forming coupler b shown above, and finally a gelatin layer containing an equal amount of the following three ultraviolet absorbers .(d), (e), and (f) in a total area concentration of 2.0 g./m. to provide a color photographic printing paper, hereinafter designated Color Printing Paper W:
  • the yellow-forming coupler of the present invention represented by the abovementioned general Formula I has a function of providing a sufficiently high color density by color development as well as the properties of providing a clear and less reddish color image fast to heat, moisture, and light.
  • a light-sensitive material for producing a colored image comprising a support and a silver halide emulsion layer thereon the improvement which comprises the layer containing a yellow-forming coupler having the formula Color Printing Paper W Coupler M wherein X is a member selected from the group consisting of a halogen atom, a lower alkoxy group, a di-alkylamino group and an aryloxy group; wherein Y is a member selected from the group consisting of a hydrogen atom, a halogen atom, a trifiuoromethyl group, a cyano group, an alkoxy group, an alkyl group, an aryloxy group, an acyl group, a carbamyl group, an acylamino group, a sulfonamino group, a sulfoamoyl group, and a carboxy alkoxy group; wherein OR represents an alkoxy group containing from 1 to 5 carbon atoms; wherein COR
  • OR is selected from the group consisting of and O O (EEO- wherein R is an alkyl group containing from to 18 carbon atoms; wherein R and R each is an alkyl group containing less than 9* carbon atoms; wherein R is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 3 carbon atoms; and wherein n represents an integer of from 2 to 5.
  • a light-sensitive material for producing a colored image comprising a support and a silver-halide emulsion layer thereon containing a yellow-forming coupler selected from the group consisting of 3-acylamino-4-methoxybenzoylaceto-Z-chloroanilide,
  • each acylamino group contains from 9 to 28 carbon atoms.
  • each acylamino group is selected from the group consisting of o artino-Qua and l 6 wherein R is an alkyl group containing from 5 to 18 carbon atoms; wherein R and R each is an alkyl group containing less than 9 carbon atoms; wherein R is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 3 carbon atoms; and wherein n represents an integer of from 2 to 5.
  • OR group is selected from the a group consisting of and wherein R is an alkyl group containing from 5 to 18 carbon atoms; wherein R and R each is an alkyl group containing less than 9 carbon atoms; wherein R is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 3 carbon atoms; and wherein n represents an integer of from 2 to 5.
  • a method of producing a colored image by developing an exposed silver halide emulsion layer with an aromatic primary amino developing agent in the presence of a yellow-forming coupler selected from the group consisting of 3-acylamino-4-methoXybenzoylaceto-2-chloroanilide,
  • R is an alkyl group containing from 5 to 18 carbon atoms; wherein R and R each is an alkyl group containing less than 9 carbon atoms; wherein R is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 3 carbon atoms; and wherein n represents an integer of from 2 to 5.
  • a yellow-forrning coupler having the formula NHCOR Y
  • X is a member selected from the group consisting of a halogen atom, a lower alkoxy group, a di-alkylamino group and an aryloXy group
  • Y is a member selected from the group consisting of a halogen atom, a trifiuoromethyl group, a cyano group, an alkoxy group, an alkyl group, an aryloxy group, an acyl group, a carbamyl group, an acylamino group, a sulfonamino group, a sulfoamoyl group, and a carboxylalkoxy group; wherein OR represents an alkoxy group containing from 1 to 5 carbon atoms; wherein COR represents an an alkoxy group containing from 1 to 5 carbon atoms; wherein COR represents an alkoxy group containing from 1 to 5 carbon atoms; wherein COR represents

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US26350A 1969-04-07 1970-04-07 Yellow-forming coupler compounds and color photographic elements containing same Expired - Lifetime US3685995A (en)

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CA (1) CA970200A (enrdf_load_stackoverflow)
CH (1) CH548622A (enrdf_load_stackoverflow)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4095983A (en) * 1975-12-16 1978-06-20 Agfa-Gevaert Ag Photographic material comprising cyclic sulfonamide substituted yellow color couplers

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61195906U (enrdf_load_stackoverflow) * 1985-05-24 1986-12-06
JPS62159207U (enrdf_load_stackoverflow) * 1986-03-31 1987-10-09
JPH01164013U (enrdf_load_stackoverflow) * 1988-05-02 1989-11-15

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4095983A (en) * 1975-12-16 1978-06-20 Agfa-Gevaert Ag Photographic material comprising cyclic sulfonamide substituted yellow color couplers

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JPS4815872B1 (enrdf_load_stackoverflow) 1973-05-17
BE748592A (fr) 1970-09-16
CA970200A (en) 1975-07-01
CH548622A (de) 1974-04-30
FR2043023A5 (enrdf_load_stackoverflow) 1971-02-12
GB1261156A (en) 1972-01-26

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