US3778277A - Light-sensitive color photographic material with bis-type yellow color coupler - Google Patents

Light-sensitive color photographic material with bis-type yellow color coupler Download PDF

Info

Publication number
US3778277A
US3778277A US00173681A US3778277DA US3778277A US 3778277 A US3778277 A US 3778277A US 00173681 A US00173681 A US 00173681A US 3778277D A US3778277D A US 3778277DA US 3778277 A US3778277 A US 3778277A
Authority
US
United States
Prior art keywords
light
photographic material
yellow
coupler
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00173681A
Other languages
English (en)
Inventor
M Fujiwhara
T Kozima
H Imamura
T Endo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Konica Minolta Inc
Original Assignee
Konica Minolta Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc
Application granted granted Critical
Publication of US3778277A publication Critical patent/US3778277A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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

Definitions

  • This invention relates to a light-sensitive color photographic material, particularly one which contains a novel bis-type yellow coupler.
  • a light-sensitive color photographic material is subjected after exposure, to color development, whereby the coupler is reacted with an oxidation product of the color developer to form a dye.
  • an u-acylacetamide derivative is used as the coupler for forming a yellow image.
  • This yellow coupler is desired to be such that is not only displays sufiicient dispersability and suificient resistance to diffusion ina photographic emulsion but also is high particularly in color purity of yellow dye formed by the color development, i.e. it gives an absorption spectral curve which shows a relatively moderate declination on the shorter wavelength region than the absorption maximum but shows a sharp declination on the longer wavelength region.
  • the yellow coupler is required to form, by the color development, a yellow dye in a high yield.
  • the layer of light-sensitive color photographic material can be made thinner, so that the photographic material is enhanced in resolution and the resulting color image is improved in sharpness.
  • the yellow coupler satisfying the above mentioned conditions is quite useful as a coupler for use particularly in a multi layer light-sensitive color photographic material.
  • German Pat. No. 1,049,231 has proposed light-sensitiive color photographic materials containing yellow couplers having the Formula I,
  • COCHzCO-R (S O CH O OR wherein R is an aromatic amine, and Q is an aliphatic, aromatic or heterocyclic residue bonded directly to the CO group.
  • D is a color density :at the absorption maximum wavelength
  • D +70 my. is a color density at the absorption maximum wavelength-F70 m i.
  • X is an alkyl group
  • Y is an alkyl, alkoxy or aralkyl group
  • Z is an aromatic amino group
  • A is a divalent organic group
  • n is or 1.
  • a solution comprising 16 g. of said methyl-a,ot,e,etetramethylpimelyl-bisacetate, 100 cc. of xylene and 40 g. of 2-chloro-5-[u-(dodecyloxycarbonyl) methoxycarbonyl] aniline was boiled, and methanol formed and the xylene were removed by azeotropic distillation. Timeafter, the liquid reaction mixture was dried under reduced pressure, and the resulting residue was recrystallized from a mixed solvent comprising n-hexane, water and methanol to obtain 28 g. of white crystals, M.P. 50-54" C., yield 53%.
  • the coupler is dissolved in a high boiling solvent having a boiling point of more than 175 C. such as tricresyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate, or, if necessary, in a mixture of said solvents, and the resulting solution is mixed with an aqueous gelatine solution containing a surface active agent. Subsequently, the mixed solution is emulsified by means of a high speed rotary mixer or a colloid mill to form a dispersion.
  • a high boiling solvent having a boiling point of more than 175 C. such as tricresyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate
  • This dispersion is added directly to a silver halide photographic emulsion, which is then coated on a suitable support such as a film base or a baryta paper and dried to remove a major proportion of the low boiling solvent, whereby a light-sensitive color photographic material can be prepared.
  • a suitable support such as a film base or a baryta paper
  • the above-mentioned dispersion is once cold set and finely cut, subjected to water washing or the like treatment to remove the low boiling solvent, and then added to a silver halide photographic emulsion. Subsequently, the emulsion is coated on said support and then dried to prepare a light-sensitive color photographic material.
  • the emulsion used in the above may be any of silver chloride, silver bromide, silver iodide, silver chlorobromide, silver chloroiodide and silver chlorobromoiodide emulsions, and may contain a chemical sensitizer, e.g. sulfur sensitizer, and a noble metal salt.
  • the emulsion may additionally contain ordinary photographic additives such as antifoggant, stabilizer, anti-stain agent, anti-irradiation agent, physical property-improving high polymer additive, coating aid, etc.
  • the emulsion may have been incorporated with a known cyanine or merocyanine dye as an optical sensitizer.
  • the light-sensitive color photographic material prepared in the above manner is exposed, developed with a developer containing a p-phenylenediamine type developing agent, and then bleached, fixed and desilvered to obtain a high density yellow dye image excellent in color purity (spectral absorption characteristic) and high in transparency.
  • This yellow dye image is excellent also in light fastness and is quite satisfactory.
  • EXAMPLE 1 20 grams of the coupler of exemplification (3) was added to a mixed solvent comprising 20 ml. of dibutyl phthalate and 60 ml. of butyl acetate, and completely dissolved therein at 80 C. This solution was mixed with 10 ml. of a 10% aqueous solution of Alkanol B (alkylnaphthalene sulfonate produced by Du Pont) and 200 ml. of a 5% aqueous gelatine solution, and the mixed solution was subjected to a colloid mill to form a dispersion. The thus formed coupler dispersion was added to 1,000 ml. of a high sensitivity silver iodobromide emulsion (5 mol percent AgI), which was then coated on a polyester film base and dried to prepare a light-sensitive color photographic material having a stable film.
  • a mixed solvent comprising 20 ml. of dibutyl phthalate and 60 ml. of butyl acetate,
  • the treated photographic material was washed with water for 5 minutes and then fixed for 5 minutes with a fixing solution of the following composition:
  • the photographic material was washed with water for 20 to 25 minutes and then dried to obtain a clear yellow dye image having an absorption maximum at 444 m which was high in color purity, favorable in sharpness and excellent in light fastness.
  • EXAMPLE 2 10 grams of the coupler of exemplification (4) was added to a mixed solvent comprising 10 ml. of tricresyl phosphate and 30 ml. of butyl acetate, and completely dissolved therein at 60 C. This solution was mixed with 5 ml. of a 10% aqueous Alkanol B solution and 200 ml. of a 5% aqueous gelatine solution, and the mixed solution was subjected to a colloid mill to form a dispersion. The thus formed dispersion was added to 500 ml. of a gelatine silver iodobromide (5 mol percent AgI) emulsion, which was then coated on a cellulose triacetate film base and dried to prepare a light-sensitive photographic material.
  • a gelatine silver iodobromide 5 mol percent AgI
  • the developed photographic material was subjected to ordinary stopping, hardening and water-washing treatments, subjected to secondary exposure by use of a white light and then developed at 20 C. for 12 minutes with a developer of the following composition:
  • the photographic material was subjected to ordinary stopping, fixing, water-washing and bleaching treatments, washed with running water for 20 minutes and then dried to obtain a yellow positive dye image having an absorption maximum at 445 m which was high in transparency, favorable in clarity (color purity) and excellent in light fastness.
  • EXAMPLE 3 16 a xenon lamp.
  • the residual ratios of the dyes at an optical The light-sensitive color photographic material as density of 1.0 were as set forth in Table 3. claimed lIl claim 3, wherem said yellow coupler 1s 01 TABLE 3 on,
  • a light-sensitive silver halide color photographic "COCH'CONH :squelnal contain ng a yellow coupler of the general fors CH; oocmco 00mm.
  • A is phenylene or alkylene.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US00173681A 1970-05-30 1971-08-20 Light-sensitive color photographic material with bis-type yellow color coupler Expired - Lifetime US3778277A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP45046030A JPS4917373B1 (enExample) 1970-05-30 1970-05-30

Publications (1)

Publication Number Publication Date
US3778277A true US3778277A (en) 1973-12-11

Family

ID=12735634

Family Applications (1)

Application Number Title Priority Date Filing Date
US00173681A Expired - Lifetime US3778277A (en) 1970-05-30 1971-08-20 Light-sensitive color photographic material with bis-type yellow color coupler

Country Status (2)

Country Link
US (1) US3778277A (enExample)
JP (1) JPS4917373B1 (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238564A (en) * 1978-06-20 1980-12-09 Ciba-Geigy Aktiengesellschaft Recording material for color photography
US4248961A (en) * 1976-12-24 1981-02-03 Ciba-Geigy Ag Material for color photography

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248961A (en) * 1976-12-24 1981-02-03 Ciba-Geigy Ag Material for color photography
US4238564A (en) * 1978-06-20 1980-12-09 Ciba-Geigy Aktiengesellschaft Recording material for color photography

Also Published As

Publication number Publication date
JPS4917373B1 (enExample) 1974-04-30

Similar Documents

Publication Publication Date Title
US3644498A (en) Yellow dye forming couplers for color photography
US3730722A (en) Yellow coupler and its use
US4009035A (en) Process for forming cyan dye photographic images
JPS5938576B2 (ja) シアン色素画像の形成方法
EP0156377B1 (en) Silver halide photographic material
JPH01254956A (ja) シアン色素生成カプラーを含有する写真材料
US4356258A (en) Silver halide color photographic material containing yellow coupler
US3002836A (en) Cyan color former for color photography
US3767411A (en) Color photographic light-sensitive material forming novel cyan images
US2304953A (en) Photographic developer
US2592363A (en) P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent
GB2032638A (en) Silver photographic material containing yellow coupler
JPS63159848A (ja) シアン色素生成カプラー含有写真要素
US3778277A (en) Light-sensitive color photographic material with bis-type yellow color coupler
GB537970A (en) Improvements in photographic processes and materials
US3337344A (en) Color photographic silver halide emulsion
US3664841A (en) Light-sensitive silver halide color photographic emulsion containing yellow-forming coupler
US2448939A (en) Thioglycolic amide couplers
US3135609A (en) 1-hydroxy-2-naphthamide couplers for color photography
US3761274A (en) Light sensitive color photographic material
US3393040A (en) Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
JPH02287453A (ja) シアン色素生成カプラー含有写真記録材料
EP0095899B1 (en) Color-forming carboxamidonaphthalene dye precursor compounds, photographic materials containing them and corresponding carboximide dyes
US3619196A (en) Light-sensitive color-photographic emulsions
US3843366A (en) Yellow forming colour couplers for photographic silver halide material