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
  • G03C7/362—Benzoyl-acetanilide couplers

Definitions

• a light-sensitive photographic color material containing a red-sensitized, a green-sensitized and a blue-sensitive silver halide emulsion layer wherein 'by the use of appropriate color couplers in the color development a cyan, magenta and yellow dyestuff image respectively is formed.
• color couplers have to meet different requirements according to the way wherein the color material is prepared and the object for which it is used.
• the color couplers shall be present in diffusionfast form in the hydrophilic silver halide emulsion layer.
• This can, be realized e.g. by using a color coupler which is sufficiently water-soluble and which is provided with a sufficiently extensive organic radical in order to prevent dilfusion of the color coupler into the hydrophilic silver halide emulsion layer, or by the use of a lipophilic color coupler which dissolved in an organic solvent is dispersed in the silver halide emulsion layer.
• color couplers which on color develpment form dyestufis which are very stable to light, humidity and heat.
• ketomethylene color couplers of the aroylacetarylide type are characterized by the presence of at least one sulfonic acid group in the aroyl part of the molecule and by the presence of at least one sulfonic acid group in the arylide part of the molecule.
• one or more sulfonic acid groups may directly be implanted on the aromatic nucleus of the aroyl group and in the same molecule one or more sulfonic acid groups may directly be implanted on the aromatic nucleus of the arylide group.
• At least one of the aromatic nuclei of the aroyland of the arylide group can be bound by means of a bivalent radical with an aromatic nucleus substituted by at least one sulfonic acid group.
• Examples of color couplers for yellow according to the 3,393,040 Patented July 16, 1968 'ice present invention wherein at least one sulfonic acid group is implanted directly on the aromatic nucleus of the aroyl group and at least one sulfonic acid group directlyon the aromatic nucleus of the arylide group, are represented by the following general formula:
• R represents a sulfonic acid group or salt form thereof
• R represents a hydrogen atom, a substitutent such as for instance a halogen atom, a sulfonic acid group or a salt form thereof, or a diffusion-fast making group such as e.g. an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms such as e.g. a n-hexadecyloxy group,
• R represents a sulfonic acid group or a salt form thereof
• R represents a hydrogen atom, a substitutent such as e.g. a halogen atom, a sulfonic acid group or a salt form thereof or a diffusion-fast making group such as e.g. an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms such as, e.g. an n-hexadecyloxy group of an n-hexadecylmercapto group, and
• R and R together can represent the necessary atoms for forming a sulfonyl substituted aromatic system which may be further substituted.
• color couplers for yellow wherein at least one sulfonic acid group in the aroyl part of the molecule is bound on an aromatic nucleus which is linked with the aromatic nucleus of the aroyl group by a bivalent radical correspond to the following general formula:
• R R4 (II) wherein R R and R have the same significance as given in Formula I,
• R represents a sulfonated aromatic radical either further substituted or not, such as e.g. a sulfonated phenyl group, and
• Y represents a bivalent radical such as e.g. a CONH group, a SO NH group or a NHCONH group.
• color couplers for yellow wherein at least one sulfonic acid group in the arylide part of the molecule is bound on an aromatic nucleus, which is linked by a bivalent radical with the aromatic nucleus of the arylide group, correspond to the following general formula:
• R R and R have the same significance as given in Formula I,
• R" represents a sulfonated aromatic radical either further substituted or not, such as e.g. a 'sulfonated phenyl group, and
• Y represents a bivalent radical such as e.g. a CONH- group or a -SO NH- group.
• R and R have the same significance as given in Formula I, Y and R' have the same significance as given in Formula II, and Y and R have the same significance as given in Formula III.
• R or R can contain a diffusion-fast making group.
• First p-n-hexadecyloxynitrobenzene is sulfonated at about 60 C. with sulfuric anhydride in tetrachloroethane.
• the reaction mixture is left for cooling overnight, the precipitate formed is separated and washed with hexane.
• the crude sulfonic acid derivative is then converted by neutralization with 2 N sodium hydroxide into the sodium salt. After salting out with aqueous sodium chloride, a white to greyish amorphous product is obtained which is recrystallized from acetonitrile.
• the 3-sulfo-4-n-hexadecyloxynitrobenzene is obtained in the form of a White crystalline product. Melting point: above 250 C.
• This nitrobenzene derivative is converted into the corsponding snlfochloride by treatment with thionylchloride at boiling temperature in the presence of dimethylformamide. After evaporating the excess of thionylchloride and treating with a mixture of benzene and hexane, the 3-chlorosulfonyl-4-hexadecyloxynitrobenzene is obtained as a light-brown to white product. Melting point: 56 C.
• this compound is allowed to react for 1 hour with potassium fluoride in acetic acid at reflux temperature. After pouring out the reaction mixture into water, separating the precipitate formed and recrystallizing from etha- 1101, the white crystalline 3-f1uorosulfonyl-4-n-hexadecyloxynitrobenzene is obtained. Melting point: 72 C.
• This nitro compound is now reduced with iron and hydrochloric acid in ethanol medium at reflux temperature. After the reduction, the reaction mixture is filtered and the amine is separated as hydrochloride. This hydrochloride is suspendcd in methylene chloride and treated with aqueous sodium dicarbonate. Hereby the amine is set free. After separating the organic layer and evaporating off the solvent, the crude product is recrystallized from acetonitrile. White needle-shaped 3-fluorosulfonyl- 4-n-hexadecyloxyaniline crystals are obtained. Melting point: 68 C.
• a color coupler for yellow wherein a sulfonic acid group in the aroyl part of the molecule is bound on an aromatic nucleus which is linked by a bivalent radical with the aromatic nucleus of the aroyl group, is men- 5 tioned a color coupler having the following structural formula:
• color couplers for yellow wherein a sulfonic acid 5 group in the arylide part of the molecule is bound on an aromatic nucleus, which is linked with a bivalent radical with the aromatic nucleus of the arylide group, correspond to the following structural formulae:
• t E from the sulfonyl fluoride derivatives, by reacting the latter with alkali can be added as such to the emulsion.
• gfg gg 'gg i i sgggg preferably 1 mol of sulfonylfiuoride derivative is dissolved in an aqueous solution of 3 mol c9 of sodium hydroxide and the resulting clear solution, after adjusting the pH to agree with the pH of the emulsion NH applied, is added to the silver halide emulsion as a 5 or 10% aqueous solution.
• the non-migratory color couplers for yellow ac- SOzF cording to the above given general formulae are, preferably immediately before coating, homogeneously mixed in dissolved form with the light-sensitive silver halide emulsion. They may also be added to the composition of According to the invention, an exposed silver halide a water-permeable non-light-sensitive layer being in direct emulsion layer is developed with an aromatic primary contact with the light-sensitive silver halide emulsion amino developing substance in the presence of the color layer or they can be incorporated into a non-light-sensicouplers for yellow according to the present invention for tive layer which is separated from the light-sensitive layer 5 obtaining photographic colorimages.
• the silver All color developing substances capable of forming azohalide emulsion contains the usual colloids such as e.g. methine dyestuifs can be utilized as developers.
• the photographic emulsion can form on color development with aromatic primary further contain usual ingredients such as hardeners, chemim amines, such as e.g.
• first color coupler containing layer of a pho- The resistance to humidity and heat of the dyestuffs tographic multilayer color material.
• Such photographic to be examined is determined from the decrease in density multilayer color material usually consists successively of of a developed wedge print after having stored, said a support, a red-senistized silver halide emulsion layer wedge print for some determined time (e.g. 7 days) at with color coupler for cyan, a green-sensitized silver halide some determined temperature (e.g. 38 C.) and relative emulsion layer with color coupler for magenta and a bluehumidity (e.g. 95%), while protected from light.
• the support for this multilayer material can idity and heat stability of dyestulfs formed by the color consist of paper, glass, cellulose nitrate, a cellulose ester development by reaction of the oxidation product of N- such as cellulose triacetate, polyester, polystyrene or any diethyl-p-phenylenediamine formed thereby with a color other synthetic or natural resin.
• silver halide emulsion layer there is usually a yellow filter
• the resistance to light of the dyestuf is formed on delayer which in most cases contains colloidal silver disp Y -PP F Y e and Which persed in gelatin.
• the sulfonylfiuoride derivatives can be are to be exammed 1S determined from file decrease in density of a developed wedge print on exposing said used as color couplers for yellow 1n the so called droplet Wedge print for some determined time 16 hours) to emulsions (cf. United States patent specification 2,304,- the light of a Xen0n Arc Fade Ometer (daylight spec 940. trum).
• a photographic multi-layer color material contain- Maximum Maximum density density after 16 Percent Formula of the color coupler at the hours of decrease beginning exposing in max. of the inXenondensity test Arc-Fade- Ometer OCwHaa Na03S COCH2CONH 1. 1.10 8. 5
• a photographic material comprising a silver halide emulsion layer and a color coupler for yellow which is a benzoylacetanilide coupler wherein the benzoyl part of the color coupler is directly substituted with at least one sulphonic acid group or substituted with a bivalent radical linked to a sulphonic acid-substituted'phenyl group, and wherein the anilide part of the color coupler is directyl substituted with at least one sulphonic acid group' or substituted with a bivalent radical linked to a sulphonic acidsubstituted phenyl group, said bivalent radical being a member of the group consisting of a CONH- group, a -SO NH- group, and a -NHCONH- group.
• a photographic multi-layer color material containing in a non-migratory form in one of the light-sensitive silver halide emulsion layers or in a non-light sensitive water permeable colloidal layer adjacent to a light-sensitive silver halide emulsion layer, a color coupler for yellow which is a benzoylacetanilide coupler wherein the benzoyl part of the color coupler is directly substituted with at least one sulphonic acid group or substituted with a bivalent radical linked to a sulphonic acid-substituted phenyl group, and wherein the anilide part of the color coupler is directly substituted with at least one sulphonic acid group or ly sensitive including a layer selected from the group consisting of a blue sensitive silver halide emulsion layer and a non-light sensitive water permeable colloidal layer adjacent thereto, at least one of said layers containing a color coupler for yellow which is a benzoylacetanilide coupler wherein the benzoyl part
• a photographic material comprising a silver halide emulsion layer and a color coupler for yellow having the general formula:
• R1 R3 CD-co-om-o Q-NHQ R5 4 wherein R is a member selected from the group consisting of a sulfonic acid group and a salt thereof;
• R is a member selected from the group consisting of a hydrogen atom and a sulfonic acid group, a salt form thereof, a halogen atom, and an organic group concontaining an acyclic aliphatic radical With 5 to 20 carbon atoms in straight line making the molecule non-migratory; and R and R together represent the necessary atoms for forming a sulfo-substitute-d aromatic system.
• a photographic material comprising a silver halide emulsion layer and a color coupler for yellow having the general formula:
• R is a member selected from the group consisting of a hydrogen atom and a sulfonic acid group, a salt form thereof, a halogen atom, and an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms in straight line making the molecule non-migratory;
• R is a member selected from the group consisting of a sulfonic acid group and asalt form thereof;
• R is a member selected from the group consisting of a hydrogen atom, and a sulfonic acid group, a salt form thereof, a halogen atom, and an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms in straight line making the molecule non-migratory; r
• R and R together represent the necessary atoms for forming a sulfo-substituted aromatic system
• R' is a sulfonated aromatic radical.
• a photographic material comprising a silver halide emulsion layer and a color coupler for yellow having 7 the general formula:
• 16 form thereof, a halogenfatom, and anorganic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms in straight line making the molecule non-migratory;
• Y is a member selected from the group consisting of a -CONH- group or a SO NH- group; and R", is a sulfonated aromatic radical.
• R is a sulfonated aromatic radical.
• R is a member selected from the group consisting of a hydrogen atom and a sulfonic acid group, a salt form thereof, a halogen atom, and an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms in straight line making the molecule non-migratory;
• R is a member selected from the group consisting of a hydrogen atom, and a sulfonic acid group, a salt form thereof, a halogen atom, and an organic group containing an acyclic aliphatic radical with 5 to 20 carbon atoms in straight line making the molecule non-migratory;
• Y is a member selected from the group consisting of w -CONH-, SO' NH- and -NHCONH-;
• R is a sulfonated aromatic radical
• Y is a member selected from the group consisting of a CONH group or a SO NH- group
• R" is a sulfonated aromatic radical.

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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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• 1963
  • 1963-07-09 BE BE634669D patent/BE634669A/xx unknown
• 1964
  • 1964-07-06 GB GB27734/64A patent/GB1062203A/en not_active Expired
  • 1964-07-07 CH CH888764A patent/CH433009A/fr unknown
  • 1964-07-08 US US381238A patent/US3393040A/en not_active Expired - Lifetime
  • 1964-07-09 FR FR981248A patent/FR1408400A/fr not_active Expired
  • 1964-07-09 DE DEG41036A patent/DE1299223B/de active Pending

Patent Citations (8)

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