US3222176A - Photographic colour images from amino substituted phenols - Google Patents

Photographic colour images from amino substituted phenols Download PDF

Info

Publication number
US3222176A
US3222176A US142334A US14233461A US3222176A US 3222176 A US3222176 A US 3222176A US 142334 A US142334 A US 142334A US 14233461 A US14233461 A US 14233461A US 3222176 A US3222176 A US 3222176A
Authority
US
United States
Prior art keywords
colour
mol
photographic
melting point
coupler
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
US142334A
Other languages
English (en)
Inventor
Jaeken Jan
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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 Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Application granted granted Critical
Publication of US3222176A publication Critical patent/US3222176A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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
    • G03C7/34—Couplers containing phenols
    • G03C7/346—Phenolic couplers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms

Definitions

  • the present invention relates to a process for the manufacture of photographic colour images by colour development in the presence of a colour coupler, to photographic material containing such colour couplers and to photographic images obtained according to this process.
  • the process for the manufacture of photographic colour images by colour development consists therein that a silver salt image is developed in an exposed photographic material with an aromatic amino developing substance in the presence of a colour coupler.
  • the colour coupler which may be present in the developing solution or in the photographic element, and the oxidation products of the aromatic amino developing substance formed during development, cooperate to produce a dyestufi image on the area where the silver image is developed.
  • the colour couplers used to produce cyan dyestuffs are generally phenols and naphthols and form indophenol dyestulfs upon coupling with the reaction product of the developing substance.
  • orthoand meta-substituted aminophenols e.g. those bearing an acylamino groups in the 2- or 5-position as described in the U.S. patent specification 2,772,162, may be used as cyan-forming colour couplers.
  • PREPARATION 3 Amixture of 77g. (0.5 mol) of Z-amino-S-nitrophenol, 105 .g. (0.55 mol) of p-toluene sulphonylchloride, 100 g. (1 mol) of calcium carbonate and 750 cm? of acetonitrile are refluxed for 90 min. After pouring out in water, sucking off, dissolution of the formed precipitate in cold 5 N aqueous sodium hydroxide, filtering oil, pouring out in 5 N aqueous hydrochloric acid, sucking off the formed precipitate, washing with water and recrystallization from toluene, 80 g. of Z-p-toluene-sulphonylamino-S-nitrophenol are obtained.
  • PREPARATION 4 A mixture of 46.2 g. (0.3 mol) of 2-amino-5-nitrophenol and 11.5 g. (0.1 mol) of methyl sulphonyl chloride in 150 cm. of acetonitrile, are refluxed for 90 min. The solvent is evaporated. On cooling the residue solidifies. After recrystallization from water containing active charcoal, 8.3 g. of Z-methyl-sulphonylamino-5-nitrophenol are obtained. Melting point: 176 C. After a second recrystallization, the melting point rises to 178 C.
  • the dyestuffs formed from this colour coupler are characterized by a very favourable absorption maximum. After development with an aromatic amino developing substance such as 2-methy1-4-diethylamino-aniline, they yield cyan dyestuffs with a bathochromatically shifted absorption maximum. Moreover, the dyestuffs obtained from the colour couplers according to the present invention are especially characterized by their excellent acid resistance. The bathochromic effect is especially prominent by the products containing a RSO NH- group in the 5-position.
  • Curve 1. is the absorption curve of the dyestuff formed during development with 2-methyl-4-diethylamino-aniline in the presence of the colour coupler prepared according to Preparation 2.
  • Absorption maximum at about 660 m Curve 2. is the absorption curve of the dyestuff formed during development with 2-methyl-4-diethylamino-aniline in the presence of the colour coupler prepared according to the U.S. patent specification No. 2,772,162.
  • the colour couplers are incorporated into photographic silver halide emulsions prepared by means of usual colloids e.g. gelatin, polyvinyl alcohol, collodion or other natural or synthetic colloids e.g. those of the Belgian patent specification 568,153.
  • colloids e.g. gelatin, polyvinyl alcohol, collodion or other natural or synthetic colloids e.g. those of the Belgian patent specification 568,153.
  • These silver halide emulsions can be coated on a support consisting of paper, glass, nitrocellulose, cellulose ester such as cellulose triacetate, polyester, polystyrene or other natural or synthetic resins, and form part of a photographic material with one or more emulsion layers.
  • Such a material is usually and essentially composed of superposed layers in the following sequence: a support, a red-sensitized emulsion layer having incorporated a cyan-forming colour coupler, a green-sensitized emulsion layer having incorporated therein a magenta-forming colour coupler and a blue-sensitive emulsion layer having incorporated therein a yellow-forming colour coupler.
  • a yellow filter layer which in most cases consists of colloidal silver, is usually applied between the blue-sensitive and the green-sensitized emulsion layer.
  • the new colour couplers are usually incorporated in the light-sensitive silver halide emulsion layer itself, but they can also be incorporated into an adjacent non-lightsensitive colloid layer or into a non-light-sensitive layer which is separated from the light-sensitive emulsion layer by a water-permeable colloid layer.
  • dialkyl-p-phenylenediamine and its derivatives such as N, N-dialkyl-N'-sulphomethyl-p-phenylene diamine and N, N-dialkyl-N'-carboxyrnethyl-p-phenylene diamine.
  • the latent silver image in the different emulsion layers is converted by colour development into,
  • photographic material is fixed, rinsed and dried again.
  • the emulsion is brought to pH 6.5 by adding N acetic acid.
  • the usual additives such as hardeners, wetting agents and stabilizing agents, the total weight is brought to 1 kg. by adding Water.
  • the emulsion is cast onto the side of a cellulose triacetate support which is provided with an antihalation layer, and dried.
  • this emulsion layer Onto this emulsion layer are cast the following layers in the indicated sequence: a gelatin layer, a green-sensitized silver brornoiodide emulsion layer containing a magenta-forming colour coupler, a yellow filter layer consisting of a gelatin layer containing colloidal silver, an unsensitized bromoiodide emulsion layer containing a yellow-forming colour coupler, and an anti-stress layer.
  • the light-sensitive photographic material thus obtained is developed in a colour developing bath of the following Then this material is rinsed for 30 sec. and fixed in an acidic fixing bath of the following composition:
  • a process for the production of photographic color images comprising the development in a photographic material of a latent silver salt image by means of a primary aromatic amino developing substance in the presence of a color coupler to form a cyan-colored indophenol dyestutf, said coupler having a formula selected from the group consisting of:
  • RCONH RSOQNH wherein each of R and R is a radical selected from the group consisting of an alkyl radical, a carboxy substituted 'alkenyl radical, an alkyl phenyl radical and a thienyl radical, one of R and R comprising an aliphatic carbon chain of 10 to 20 carbon atoms.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US142334A 1960-10-04 1961-10-02 Photographic colour images from amino substituted phenols Expired - Lifetime US3222176A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE2040105 1960-10-04

Publications (1)

Publication Number Publication Date
US3222176A true US3222176A (en) 1965-12-07

Family

ID=3864736

Family Applications (1)

Application Number Title Priority Date Filing Date
US142334A Expired - Lifetime US3222176A (en) 1960-10-04 1961-10-02 Photographic colour images from amino substituted phenols

Country Status (4)

Country Link
US (1) US3222176A (de)
BE (1) BE595694A (de)
DE (1) DE1109523B (de)
GB (1) GB955009A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3607345A (en) * 1958-04-26 1971-09-21 Eastman Kodak Co Process for coating photographic emulsion layers
US3721823A (en) * 1968-08-22 1973-03-20 Agfa Gevaert Nv Color radiography
US4124396A (en) * 1977-03-03 1978-11-07 Eastman Kodak Company 2,5-Dicarbonylaminophenol dye-forming couplers
US4200466A (en) * 1975-09-30 1980-04-29 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials
EP0011567A1 (de) * 1978-11-15 1980-05-28 EASTMAN KODAK COMPANY (a New Jersey corporation) Photographisches Element das ein diffusionsfestes 2,5-Disulfonamidophenol enthält, das oxydierte elektronenübertragende Verbindungen abfängt
EP0201033A2 (de) 1985-04-30 1986-11-12 Konica Corporation Verfahren zur Behandlung farbphotographischer Silberhalogenidmaterialien
EP0204530A2 (de) 1985-05-31 1986-12-10 Konica Corporation Verfahren zur Herstellung eines direkt positiven Farbbildes
EP0228914A2 (de) 1985-12-28 1987-07-15 Konica Corporation Verfahren zur Behandlung eines lichtempfindlichen farbphotographischen Silberhalogenidmaterials
US4988614A (en) * 1988-09-27 1991-01-29 Konica Corporation Silver halide color photographic light-sensitive material containing novel magenta couplers
US5523199A (en) * 1994-12-06 1996-06-04 Eastman Kodak Company Photographic element and process employing magenta azine dye-forming couplers

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2350138A (en) * 1940-08-22 1944-05-30 Eastman Kodak Co Nondiffusing acylacetyl sulphonamide coupler
US2536010A (en) * 1947-07-11 1950-12-26 Gen Aniline & Film Corp Preparation of azine dyestuff images
CA478527A (en) * 1951-11-13 Albert C. Starke, Jr. Light sensitive emulsions containing color formers capable of yielding non-migratory azine dyestuffs
US2772162A (en) * 1954-11-03 1956-11-27 Eastman Kodak Co Diacylaminophenol couplers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA478527A (en) * 1951-11-13 Albert C. Starke, Jr. Light sensitive emulsions containing color formers capable of yielding non-migratory azine dyestuffs
US2350138A (en) * 1940-08-22 1944-05-30 Eastman Kodak Co Nondiffusing acylacetyl sulphonamide coupler
US2536010A (en) * 1947-07-11 1950-12-26 Gen Aniline & Film Corp Preparation of azine dyestuff images
US2772162A (en) * 1954-11-03 1956-11-27 Eastman Kodak Co Diacylaminophenol couplers

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3607345A (en) * 1958-04-26 1971-09-21 Eastman Kodak Co Process for coating photographic emulsion layers
US3721823A (en) * 1968-08-22 1973-03-20 Agfa Gevaert Nv Color radiography
US4200466A (en) * 1975-09-30 1980-04-29 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials
US4124396A (en) * 1977-03-03 1978-11-07 Eastman Kodak Company 2,5-Dicarbonylaminophenol dye-forming couplers
EP0011567A1 (de) * 1978-11-15 1980-05-28 EASTMAN KODAK COMPANY (a New Jersey corporation) Photographisches Element das ein diffusionsfestes 2,5-Disulfonamidophenol enthält, das oxydierte elektronenübertragende Verbindungen abfängt
EP0201033A2 (de) 1985-04-30 1986-11-12 Konica Corporation Verfahren zur Behandlung farbphotographischer Silberhalogenidmaterialien
EP0204530A2 (de) 1985-05-31 1986-12-10 Konica Corporation Verfahren zur Herstellung eines direkt positiven Farbbildes
EP0228914A2 (de) 1985-12-28 1987-07-15 Konica Corporation Verfahren zur Behandlung eines lichtempfindlichen farbphotographischen Silberhalogenidmaterials
US4988614A (en) * 1988-09-27 1991-01-29 Konica Corporation Silver halide color photographic light-sensitive material containing novel magenta couplers
US5523199A (en) * 1994-12-06 1996-06-04 Eastman Kodak Company Photographic element and process employing magenta azine dye-forming couplers

Also Published As

Publication number Publication date
BE595694A (de)
GB955009A (en) 1964-04-08
DE1109523B (de) 1961-06-22

Similar Documents

Publication Publication Date Title
US3408194A (en) Silver halide emulsion layers containing yellow dye forming couplers
US2772162A (en) Diacylaminophenol couplers
US2808329A (en) Photographic color correction using colored and uncolored couplers
US2998314A (en) Color photography
US3615505A (en) Silver halide emulsion containing 2-pyrazolin-5-one color coupler
US3222176A (en) Photographic colour images from amino substituted phenols
US3563745A (en) Silver halide photographic materials containing 1-arylmethyl-2-pyrazolin-5-one color couplers
US3013879A (en) Production of color photographic images
US3245788A (en) Production of color photographic images
US3656950A (en) Color photographic processes
US4095983A (en) Photographic material comprising cyclic sulfonamide substituted yellow color couplers
JP2001188329A (ja) 写真要素及び写真カプラー
US3419390A (en) Elements and developers for color photography utilizing phenolic couplers containingan aminoalkyl group on the coupling position
US3930861A (en) Silver halide emulsions containing 3-anilino-2-pyrazolin-5-one color couplers
US3762921A (en) Photographic colour material
US3249431A (en) Production of color photographic images
US2865751A (en) 1-alkyl-3-acylamido-5-pyrazolone couplers for color photography
US2448939A (en) Thioglycolic amide couplers
US2728660A (en) Salicylic acid ester and amide photographic coupler compounds
US2500487A (en) Yellow diffusion-fast color formers of the benzimidazole class
US3462270A (en) Color photography utilizing 1-fluoroalkyl - 2 - pyrazoline - 5 - one colour couplers
US3843366A (en) Yellow forming colour couplers for photographic silver halide material
US3884700A (en) Silver halide emulsions containing two-equivalent benzoylacetanilide photographic couplers
US2527476A (en) Cyanoacetylhydrazones as photographic color couplers
US3008827A (en) Production of colored photographic images