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
  • G03C7/333—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
• • C—CHEMISTRY; METALLURGY
  • C21—METALLURGY OF IRON
  • C21D—MODIFYING THE PHYSICAL STRUCTURE OF FERROUS METALS; GENERAL DEVICES FOR HEAT TREATMENT OF FERROUS OR NON-FERROUS METALS OR ALLOYS; MAKING METAL MALLEABLE, e.g. BY DECARBURISATION OR TEMPERING
  • C21D9/00—Heat treatment, e.g. annealing, hardening, quenching or tempering, adapted for particular articles; Furnaces therefor
  • C21D9/70—Furnaces for ingots, i.e. soaking pits

Definitions

• This invention relates to color photography and particularly to color couplers for use in photographic processes.
• Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images "upon photographic development'are well known.
• these color-forming-compounds of couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporated in'the. emulsion layer and the unused coupler remains after'formation of the colored image.
• the coupler is used in the developing'solution,it may be colored without detriment to the final image" and certain colored couplers have been used in this way.
• I T N- B especially ⁇ a'mononuclear aryl radical such as phenyl or substituted phenyl, a mononuclear aryloxyphenyl radical such as p-tertiary-butylphenoiryphenyl, p-tert.-amylphenoxyphenyl, 2,4-
• d-iamylnhenoxyphenyl or phenoxypnenyl or an active po'sitionof the coupler issubstituted with an azo group --and this .group is split offi or removed by the oxidized developer when thea'zosubstituted coupler is treated with the-oxidized developer either in aqueous solution or in the photographic emulsion layer.
• the coupler may be converted to a difierently colored compound and the azo .group readily -removed;trom it by means oi :reaction wi-th the oxidized deasarpoa OOl lehydroxy-l-phenylazo-N-isoamyl-2maphthanilide 1-hydroxy-4- (2 metl1oxy-4-nitrophenylazo -N-is0amyl- 2-naphthanilide 3 C H3 00 Ha 1-hydroxy-4- [Z-methoxyl- (o-methoxyphenylazo) phenylazo] -N-isoamyl2-naphthanilide Our compounds may be incorporated either in the developing solution or in the emulsion layer according to their intended use and diffusion characteristics.
• the Hanson process involves a color correction method in which a color coupler is incorporated in the photographic emulsion layer prior to exposure and upon development is con.- verted to a colored image where theJayer is eX-- posed.
• the coupler remaining in the: unexposedportions of the layer retains itsv original color and by suitable choiceof the colorofthe original coupler and the color of the final dye image, a masking or correction effect can be obtained.
• the compounds employed according to our invention may be prepared by any suitable method such as by reaction of the naphthamide with the appropriate diazonium compound.
• compound No. 1 was prepared as follows:
• l hydroxy 4' (p-tert. butylphenoxy) -2- naphthanilide was prepared by the condensation of equi-molecular quantities of phenyl l-hydroxy-2-naphthoate and p-(p-tert-butylphenoxy-) -aniline at 200 for one hour.
• the product was purified by recrystallizationfrom a mixture of benzene and ligroin.
• the p (p-tert.-butylphenoxy) aniline was prepared by alkali condensation of hot p-nitro chlorobenzene and p-tert-butylphenol followed by catalytic reduction of the nitro compound in the presence of Raney nickel.
• Coupler Diazonium salt o-methoxybenz-ene diazonlum chloride.
• diazonium chloride 4' 1-hydroxy-4-(p-tert.-butylphe- Z-meth o xylenitronoxy) -2-naphthanilide.
• benzene diazonium f chloride 5.----- l-hydroxy-4'- (p-tert.-butylpl1e- 2-n1ethoxy4-pl1enylnoxy) -2-naphtlianilide. azobenzene diazonium chloride.
• Compound No. 6 was: prepared as follows:
• the ,4- (p-tert-.-amylphenoxy-)aniline was preparedby the condensation of hot p-nitrochlorobenzene and p-terteamylphenol in alkali to yield 4 (p tert. amylphenoxy)nitrobenzene.
• 1-- hydroxy--(o met-hoxyphenylazo)-4'-(ptert. amylphenoxy)-2-naphthanilide (6) was prepared by adding an equivalent solution of 1.05 mols of omethoxybenzene diazonium chloride to 1 mol of 1hydroxy-4-(p-tert.-amy1phenoxy)-2- naphthanilide in 8 liters of pyridine ethanol (1:1) solution at 5 C. The product was isolated by pouring the mixture into an excess of hydrochloric acid. The pure dye was obtained by crystallization from dioxane or acetic acid.
• Compound No. 8 was prepared in the following manner:
• the final compound was prepared by the simple treatment of 1 hydroxy-N- ⁇ i-[2-(2,4-diamylphenoxy) 5-(3,5-dichlorosulfonylbenzamido) benzamido] phenethyl ⁇ 2-naphthamide with benzene diazonium chloride.
• Compound 9 was prepared by the condensation in ether of two equivalents of N-methylaniline with 1 equivalent of l-hydroxy-Z-naphthoyl chloride to produce l-hydroxy-N-methyl- 2-naphthanilide.
• the final compound was prepared by treating this intermediate with o-carbethoXy-benzene diazonium chloride.
• Compound 10 was prepared by the condensation in ether of 2 equivalents of N-isoamylaniline with 1 equivalent of 1-hydroxy-2-naphthoyl chloride to produce l-hydroxy-N-isoamyl-Z- naphthanilide. This intermediate was treated with benzene diazonium chloride to produce the final compound.
• the primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols.
• the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
• Suitable compounds Grams 2-amino-5-diethyl-amino toluene HCl 2 Sodium sulphite 2 Sodium carbonate Potassium bromide 2 Water .to V1 liter.
• X is selected from the class consisting of hydrogen and alkyl radicals
• Y is selected from the class consisting of mononuclear aryl radicals and aralkyl radicals
• R is a mononuclear aryl radical
• X is selected from the class consisting of hydrogen and alkyl radicals
• Y is selected'from the class consisting of mononuclear aryl radicals and aralkyl radicals and R is a mononuclear aryl radical
• Y is a mononuclear aryl-oxyphenyl radical and R is a mononuclear aryl radical
• X is selected from the class consisting of hydrogen and alkyl radicals
• Y is selected from the class consisting of mononuclear aryl radicals, aralkyl radicals and R is a mononuclear aryl radical.
• O ONH-Y N NR Where Y and R are mononuclear aryl radicals.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Physics & Mathematics (AREA)
• Materials Engineering (AREA)
• Crystallography & Structural Chemistry (AREA)
• Mechanical Engineering (AREA)
• Thermal Sciences (AREA)
• Metallurgy (AREA)
• Organic Chemistry (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Developing Agents For Electrophotography (AREA)

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Cited By (18)

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Citations (8)

• 0
  • BE BE480525D patent/BE480525A/xx unknown
  • BE BE476362D patent/BE476362A/xx unknown
• 1946
  • 1946-08-29 FR FR950288D patent/FR950288A/fr not_active Expired
• 1947
  • 1947-03-13 US US734548A patent/US2521908A/en not_active Expired - Lifetime
  • 1947-07-10 GB GB18258/47A patent/GB627814A/en not_active Expired
  • 1947-07-28 FR FR950228D patent/FR950228A/fr not_active Expired
  • 1947-12-23 CH CH285169D patent/CH285169A/fr unknown
  • 1947-12-23 CH CH283456D patent/CH283456A/fr unknown
• 1948
  • 1948-02-16 FR FR980372D patent/FR980372A/fr not_active Expired
  • 1948-04-06 ES ES0183158A patent/ES183158A1/es not_active Expired

Patent Citations (8)

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