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
  • G03C7/344—Naphtholic couplers

Definitions

• the color couplers are stable to light and heat and do not influence the viscosity of a gelatin silver halide emulsion when incorporated therein.
• the present invention relates to the production of coloured photographic images by colour development. It relates more particularly to novel cyan-forming colour couplers and to light-sensitive silver halide emulsion materials containing them.
• the colour couplers suitable for use in silver halide materials have to meet the following main requirements: they should be fast to diffusion and react quickly and as completely as possible on colour development, yielding a colour image that absorbs light in a desired spectral region and that possesses a fastness to light as Well as a stability against humidity and heat as high as possible, particularly when produced in a positive or reversal material.
• the colour couplers should also meet requirements of technological nature, which are of importance when preparing and coating the silver halide emulsion, e.g. the addition of the colour coupler to the emulsion may not involve an increase of the viscosity of the light-sensitive emulsion beyond allowable limits and/ or it may not give rise to great changes in viscosity with time.
• X represents a halogen atom e.g. a chlorine, bromine or fluorine atom, preferably a chlorine atom,
• R represents an aliphatic radical comprising at least 5 and most 20 carbon atoms, preferably a linear aliphatic carbon chain having at least 10 carbon atoms
• Z represents a hydrogen atom or a substituent e.g. a halogen atom such as a chlorine atom, a bromine atom or a fluorine atom, a phenyl group, an alkyl group such as a methyl, t-butyl, t-octyl, an aralkyl group such as a benzyl group, an alkoxy group such as a methoxy group, or a substituted amino group such as a dimethyl amino group.
• a substituent e.g. a halogen atom such as a chlorine atom, a bromine atom or a fluorine atom, a phenyl group, an alkyl group such as a methyl, t-butyl, t-octyl, an aralky
• Colour couplers of the same kind as those according to the present invention which correspond to the above general formula with the diflerence however that X represents a sulphonic acid group, are described in U .K. patent specification 914,507 filed May 25, 1961 by General Anilin & Film Corporation.
• the colour couplers according to this UK. patent specification adversely affeet the viscosity of the emulsion and give rise to dyeimages which are less stable against light and heat than those according to the present invention.
• the colour couplers for cyan according to the present invention can be prepared by allowing to react the phenylester of a 1 hydroXy-4-halogen-Z-naphthoic acid with the appropriate aromatic amine.
• the requisite aniline with a long chain alkoxy group in ortho position can be obtained by methods known in the organic chemical art, and the detailed preparation of such aniline compounds is not deemed necessary since the preparation will not give rise to difliculties to a technician skilled in organic chemistry.
• the colour couplers of the invention can be homogeneously incorporated into a hydrophilic colloid composition according to one technique by first dissolving them in an alkaline solution of a water-miscible organic solvent e.g. ethanol, which may be mixed to some extent with water, and according to other techniques by first dissolving them in an organic solvent as described e.g. in the published Dutch patent applications 5/ 16423 and 65/ 16424 both filed Dec. 16, 1965 by Gevaert-Agfa N.V., in the published Dutch patent application 66/00098 and 66/00099 both filed Jan. 5, 1966 by Gevaert-Agfa NV. and in the published Dutch patent application 66/ 00628 filed Jan.
• a water-miscible organic solvent e.g. ethanol
• They may also be added to the composition of a water-permeable non-light-sensitive layer, which is in direct contact with the light-sensitive silver halide emulsion layer, or they may be incorporated into a non-light-sensitive layer, which is separated from the light-sensitive layer by a water-permeable non-light-sensitive layer.
• the silver halide emulsion usually contains colloids such as gelatin, poly(vinyl alcohol), colloidion or other suitable natural or synthetic colloids.
• colloids such as gelatin, poly(vinyl alcohol), colloidion or other suitable natural or synthetic colloids.
• the photographic emulsion may further contain usual ingredients such as hardeners, chemical sensitizing agents, optical sensitizing agents, plasticizers, development accelerators, stabilizing agents and wetting agents.
• the non-migratory colour couplers for cyan described in the present invention are preferably incorporated in the red-sensitized silver halide emulsion layer of a positive or reversal photographic colour material.
• said silver halide emulsion is coated as the first colour coupler containing layer of a photographic multilayer colour material.
• Such photographic multilayer colour material usually comprises in the given sequence a support, a red-sensitized silver halide emulsion layer with a colour coupler for cyan, a green-sensitized silver halide emulsion layer with a colour coupler for magenta and a blue-sensitive silver halide emulsion layer with a colour coupler for yellow.
• the support of this multi-layer material may consist of paper, glass, cellulose nitrate, a cellulose ester such as cellulose triacetate, polyester, polystyrene or another synthetic or natural resin.
• a yellow filter layer generally comprising colloidal silver dispersed in gelatin is usually provided between the silver halide emulsion layer containing a colour coupler for yellow and the green-sensitized silver halide emulsion layer.
• the exposed silver halide emulsion layer containing the colour coupler for cyan according to the present invention is developed preferably with an aromatic primary amino developing substance.
• Aromatic primary amino compounds such as p phenylenediamine and derivatives such as N,N diethyl p phenylenediamine, N,N diethyl N sulphomethyl-p-phenylenediamine and N,N diethyl N carboxymethyl-p-phenylenediamine are preferably used.
• each of the emulsion portions is coated onto a cellulose triacetate support in such a way that the emulsion layers obtained after drying all have the same thickness.
• the light-sensitive materials R, S, T and U are examined as to their fastness to light in an apparatus known as Xenotest wherein the bleaching exposure is carried out by means of a Xenon arc lamp.
• Xenotest apparatus is marketed by the firm Quarzlampen Deutschen m.b.h. Hanau, Germany.
• X represents a halogen atom
• R represents an aliphatic radical comprising at least 5 and at most 20 carbon atoms
• Z represents a hydrogen atom or a substituent selected from the group consisting of halogen, alkyl, aralkyl, phenyl, alkoxy and alkyl substituted amino.
• the photographic emulsion of claim 1 which includes a water-permeable colloid as a carrier for the silver halide grains.
• a photographic multilayer color material containing in a red-sensitized silver halide emulsion layer a color coupler for cyan having the formula:
• X represents a halogen atom
• R represents an aliphatic radical comprising at least 5 and at most 20 carbon atoms
• Z represents a hydrogen atom or a substituent selected from the group consisting of halogen, alkyl, aralkyl, phenyl, alkoxy and alkyl substituted amino.
• a method of producing a cyan colored photographic image in a photographic material containing a lightsensitive silver halide emulsion comprises exposing said material to light and color developing it, by allowing to react a color coupler having the formula:

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (11)

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Citations (2)

• 1965
  • 1965-07-28 GB GB32198/65A patent/GB1099418A/en not_active Expired
• 1966
  • 1966-07-11 US US564016A patent/US3488193A/en not_active Expired - Lifetime
  • 1966-07-27 NL NL6610577A patent/NL6610577A/xx unknown
  • 1966-07-27 DE DE19661522391 patent/DE1522391A1/de active Pending
  • 1966-07-28 BE BE684689D patent/BE684689A/xx unknown

Patent Citations (2)

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