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 PDFInfo
- 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
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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
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)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP45046030A JPS4917373B1 (de) | 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 (de) |
JP (1) | JPS4917373B1 (de) |
Cited By (2)
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 |
-
1970
- 1970-05-30 JP JP45046030A patent/JPS4917373B1/ja active Pending
-
1971
- 1971-08-20 US US00173681A patent/US3778277A/en not_active Expired - Lifetime
Cited By (2)
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 (de) | 1974-04-30 |
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