DE3613020A1 - Photosensitive, colour-photographic recording material for copying purposes - Google Patents

Abstract

The invention relates to a photosensitive, colour-photographic recording material which is suitable for copying purposes, having a reflective layer support and at least one blue-, green- and red-sensitive silver-halide emulsion layer. The green-sensitive silver-halide emulsion layer contains a monodisperse silver-halide emulsion. To this is allocated a magenta coupler of the formula: <IMAGE> in which: Z is a group of nonmetallic atoms necessary for the formation of an optionally substituted, nitrogen-containing heterocyclic ring; X is a substituent which can be removed on reaction with a product of the oxidation of a colour developer compound, and R is a hydrogen atom or a substituent. The recording material described is distinguished by particularly good gradation properties.

Description

DESCRIPTION

"Light-sensitive color photographic recording material too Copying purposes "The invention relates to a photosensitive device suitable for copying purposes color photographic recording material, in particular one suitable for copying purposes light-sensitive color photographic recording material with excellent gradation properties.

Usually this is the case with negative / positive color photography photographing object recorded on color negative film by means of a camera, creating a negative image. This is then on by means of a copier A color copy paper is copied, which ultimately results in a color copy or a color image receives. One of the most important factors for improving the quality of such color copies or color images are based on the gradation properties of the color copy paper.

When the gradation properties of color copy paper are unsuitable i.e. if, for example, the gradation of the paper is too hard, that leaves it on the paper in question copied image especially in the low- and high-density Image parts leave something to be desired with regard to the (image) reproduction. If on the other hand the gradation is too soft, the image copied onto the paper in question only comes out dull and washed out. In no case is the quality of the color copy obtained satisfactory.

You will not get a qualitatively acceptable color copy if only the Satisfy gradation properties of a single silver halide emulsion layer. In subtractive color photography, the three colors, namely blue-green, Pure red and yellow, from high highlight areas to shadow areas be well balanced with each other in a scene.

For example, if the gradation in the high density areas is a Purple developing layer with respect to the gradation of the other colors developing Layers is softer, the shadow areas of the layer change from black to Greenish black. On the other hand, if the gradation of this layer with respect to the If other layers are too hard, their shadow area changes to reddish-black. In any case, the result is a poor one, particularly in terms of color rendering Color copy. As already stated, the gradation properties are more sensitive to light color photographic recording materials for copying purposes both with regard to on the tonal value reproduction as well as the color reproduction of particular importance. There is therefore a need for a way of making a suitable gradation to be able to take care of.

As is well known, the amount of silver applied can be used to control the gradation change. Although this is the easiest way to control gradation, is disadvantageous in that the maximum density varies. Hence, this is suitable Technology only for fine adjustment and the like.

Another measure is to have a single layer or separate one Layers a plurality of silver halide grains harder than those at a desired gradation and the same color sensitivity with each other as well as one have different color sensitivity to each other.

This measure is well known in the photographic art Technique. Although this technique can theoretically be used to achieve any gradation can achieve is their application in practice in large-scale implementation due to limited options, high costs and the like using this technique alone will not derive any practical benefit can.

There are other known gradation adjustment measures in the Preparation of light-sensitive silver halide emulsions. An example of this is the so-called hardening technique, in which in the context of a physical ripening doping with metal ions, e.g.

Rhodium or iridium ions. In another technique, the conditions necessary for the production of silver halide grains are appropriately selected. An example of such a technique is the so-called. Single jet precipitation process, which is suitable for preparing a soft emulsion, and the so-called double jet precipitation process, which is suitable for preparing a hard emulsion. Furthermore, in the preparation of the silver halide grains, the pAg and pH values and the compositional distribution of each silver halide can also be appropriately selected. In another known method, the conditions required for each chemical sensitization are appropriately selected. The desired gradation can be achieved by using the mentioned techniques individually or in combination. In most cases, however, this leads to an impairment of the other photographic properties, for example the Sensitivity or fog, reproduction errors, deterioration in latent image stability, deterioration in printing resistance and the like, or difficulties in manufacture. In addition, it creates considerable difficulties in determining the most favorable conditions for each individual case. Thus, the techniques outlined are of limited use in practice.

To reproduce colors in a subtractive color process with a silver halide photographic light-sensitive recording material including a color photographic light-sensitive material for copying purposes one needs a yellow coupler, a magenta coupler and one Cyan couplers, each produced by coupling reaction with the oxidation products of a primary aromatic amine color developing agent is yellow, purple-red or provide a cyan dye image. The gradation can now also be changed by considering the nature of the couplers mentioned and their substituents a suitable Makes a choice. This technique also causes difficulties in practice, since in its Application of undesirable changes in the other properties of the photosensitive Recording material, e.g. the spectral properties of the dye images, the Stability of dye images and the like, changes are noted.

From JP-OS 40550/1983 it is known that the areas of high lights can be made softer if a suitable high-boiling solvent is used for the coupler. Another gradation setting technique is known from JP-OS 213161/1984 in which a suitable high-boiling solvent is selected and a catechol derivative is also used. It has has shown that special density areas of special emulsion layers can be improved by these measures, but that nevertheless the overall gradation, the gradation compensation and the like still leave something to be desired.

Extensive investigations have shown that an acceptable gradation and an acceptable gradation compensation for the blue- and red-sensitive emulsion layers can achieve that, however, at one green-sensitive emulsion layer is not the case. Ultimately, you can so far still no light-sensitive color photographic material Produce copying purposes that are fully satisfactory in its gradation properties is.

In other words, it can be done in practice the measures outlined not inexpensive and in terms of its color photographic Properties stable light-sensitive color photographic recording material for copying purposes, which is characterized by excellent gradation properties as well as excellent other photographic properties.

The invention had the object of providing a light-sensitive color photographic Specify recording material for copying purposes that changes with constant Quality and inexpensive to produce, color copies supplies from the areas high lights up to the shadow areas a good color balance and a good one Show color rendering, and excellent in addition to the usual photographic properties Has gradation properties.

The invention thus provides a light-sensitive color photographic recording material for copying purposes with a reflective layer support on which at least one blue-sensitive, green-sensitive and red-sensitive silver halide emulsion layer is applied, which is characterized in that the silver halide emulsion of the green-sensitive silver halide emulsion layer is a monodisperse silver halide emulsion and that with this monodisperse silver halide emulsion a magenta coupler of the formula: wherein: Z represents a group of non-metallic atoms required to form an optionally substituted nitrogen-containing heterocyclic ring; X is a substituent which can be split off upon reaction with an oxidation product of a color developing agent, and R is a hydrogen atom or a substituent.

Examples of substituents R in formula (I) are halogen atoms, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or aryl groups, heterocyclic groups, acyl, sulfonyl, sulfinyl, phosphonyl, carbamoyl, sulfamoyl or cyano groups, residual groups of spiro compounds or crosslinked hydrocarbon compounds or . , Alkylthio and arylthio groups and heterocyclic thio groups.

Halogen atoms which can be represented by R are, for example, chlorine and bromine atoms, especially the chlorine atom.

Alkyl groups which can be represented by R are, for example, those with 1 - 32 carbon atom (s). Alkenyl and alkynyl groups which can be represented by R are for example those with 2 to 32 carbon atoms each. Representable by R. Cycloalkyl and cycloalkenyl groups are, for example, those with 3 - 12 each, preferably 5-7 carbon atoms. The alkyl, alkenyl and alkynyl groups can be straight or branched chain.

Furthermore, the alkyl, alkenyl, alkynyl, Cycloalkyl and cycloalkenyl groups, for example through halogen atoms, heterocyclic Groups or aryl, cyano, cycloalkyl or cycloalkenyl groups or residual groups substituted by spiro compounds or crosslinked hydrocarbon compounds be. The substituents mentioned can in turn be replaced by a carbonyl group, e.g. one of acylcarboxy, carbamoyl, alkoxycarbonyl or aryloxycarbonyl radicals, be substituted. Furthermore, the substituents mentioned can in turn have a Heteroatom, in a typical way via an oxygen atom e.g. with Hydroxy, alkoxy, aryloxy, heterocyclic oxy, siloxy, acyloxy or carbamoyloxy groups, via a nitrogen atom, e.g. with nitro or amino groups, e.g. dialkylamino, Sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, acylamino, sulfonamido, Imido or ureido groups, via a sulfur atom, e.g. with alkylthio, arylthio, heterocyclic thio, sulfonyl, sulfinyl or sulfamoyl groups, or via a Phosphorus atom, e.g.

with phosphonyl groups.

Examples of the substituents mentioned are methyl, ethyl, isopropyl, tert-butyl, pentadecyl, heptadecyl, 1-hexylnonyl, 1,1'-dipentylnonyl, 2-chlorotert.-butyl, Trifluoromethyl, 1-ethoxytridecyl, 1-methoxyisopropyl, methanesulfonylethyl, 2,4-di-tert. -amylphenoxymethyl-, anilino-, 1-phenylisopropyl-, 3-m-butanesulfonaminophenoxypropy1-, 3,4 '- {@ - [4 "- (p-Hydroxybenzenesulfonyl) -phenoxy] -dodecanoylamino} -phenylpropyl-, 3- {4' - [# - (2", 4 "-di-tert.-amylphenoxy) -butanamido] -phenyl} -propyl-, 4 - [# - (o-chlorophenoxy) tetradecanamidophenoxy] propyl, aryl, cyclopentyl or Cyclohexyl groups.

Aryl groups which can be represented by R are preferably optional alkyl, alkoxy or acylamino substituted phenyl groups. Typical examples of this are phenyl, 4-tert-butylphenyl, 2,4-di-tert-amylphenyl, 4-tetradecanamidophenyl, Hexadecyloxyphenyl or 4 '- [# - (4 "-tert-butylphenoxy) -tetradecanamido] -phenyl groups.

Heterocyclic groups that can be represented by R are preferably 5- up to 7-membered heterocyclic groups, which are optionally substituted or condensed could be. Typical examples are 2-furyl, 2-thienyl, 2-pyrimidinyl and 2-benzothiazolyl groups.

Acyl groups that can be represented by R are, for example, acetyl, phenylacetyl, Dodecanoyl, alkylcarbonyl, e.g. a-2,4-di-tert.-amylphenoxybutanoyl, benzoyl, 3-pentadecyloxybenzoyl and arylcarbonyl, e.g.

p-chlorobenzoyl groups.

The sulfonyl groups that can be represented by R are, for example, alkylsulfonyl, e.g. methylsulphonyl and dodecylsulphonyl as well as arylsulphonyl, e.g. benzenesulphonyl and p-toluenesulfonyl groups.

The sulfinyl groups that can be represented by R are, for example, alkylsulfinyl, e.g. ethylsulfinyl, octylsulfinyl or 3-phenoxybutylsulfinyl and arylsulfinyl, e.g.

Phenylsulfinyl or m-pentadecylphenylsulfinyl groups.

The phosphonyl groups that can be represented by R are, for example, alkylphosphonyl, e.g. butyloctylphosphonyl, alkoxyphosphonyl, e.g. octyloxyphosphonyl, aryloxyphosphonyl, e.g. phenoxyphosphonyl and arylphosphonyl or phenylphosphonyl groups.

In the case of the carbamoyl groups which can be represented by R, their alkyl and aryl, preferably phenyl, groups. Examples of such carbamoyl groups are N-methylcarbamoyl-, N, N-dibutylcarbamoyl-, N- (2-pentadecyloxyethyl) -carbamoyl-, N-ethyl-N-dodecylcarbamoyl and N- [3- (2,4-di-tert-amylphenoxy) propyl] carbamoyl groups.

In the sulfamoyl groups that can be represented by R, their alkyl or aryl groups, preferably phenyl groups, may be substituted. Examples of such Sulfamoyl groups are N-propylsulfamoyl, N, N-diethylsulfamoyl, N- (2-penta decyloxyethyl) sulfamoyl, N-ethyl-N-dodecylsulfamoyl and N-phenylsulfamoyl groups.

A residual group of a spiro compound that can be represented by R is, for example the spiro [3.3] heptan-1-yl group.

Examples of residual groups of crosslinked hydrocarbon compounds that can be represented by R. and bridging hydrocarbon compounds are bicyclo [2.2.1] heptan-1-yl, tricyclo [3.3.1. 13.7] decan-1-yl and 7,7-dimethylbicyclo [2.2.1] heptan-1-yl groups.

Alkoxy groups which can be represented by R can be replaced by substituents such as they are indicated for the alkyl groups which can be represented by R, be substituted. Examples include methoxy, propoxy, 2-ethoxyethoxy, pentadecyloxy, 2-dodecyloxyethoxy and phenethyloxyethoxy groups.

The aryloxy group which can be represented by R is preferably the phenoxy group. All aryloxy groups that can be represented by R can be represented in the aryl nucleus by substituents, as indicated for the aryl groups which can be represented by R, may be substituted. Examples are phenoxy, p-tert-butylphenoxy and m-pentadecylphenoxy groups.

Heterocyclic oxy groups which can be represented by R are preferred those with an optionally substituted 5- to 7-membered heterocyclic Ring. Examples are 3,4,5,6-tetrahydropyranyl-2-oxy and 1-phenyltetrazole-5-oxy groups.

The siloxy groups which can be represented by R can optionally be alkyl-substituted be. Examples are trimethylsiloxy, triethylsiloxy and dimethylbutylsiloxy groups.

Acyloxy groups which can be represented by R are, for example, alkylcarbonyloxy and arylcarbonyloxy groups which are optionally substituted. examples for such groups are acetyloxy, α-chloroacetyloxy and benzoyloxy groups.

The carbamoyloxy groups which can be represented by R can be alkyl- or aryl-substituted be. Examples are N-Ethylcarbamoyloxy-, N, N-Diethylcarbamoyloxy- and N-phenylcarbamoyloxy groups.

The amino groups represented by R can be alkyl or aryl, preferably be phenyl substituted. Examples are ethylamino, anilino, m-chloroanilino, 3-pentadecyloxycarbonylanilino and 2-chloro-5-hexadecanamidoanilino groups.

The acylamino groups that can be represented by R are, for example, alkylcarbonylamino or arylcarbonylamino, preferably phenylcarbonylamino groups, which optionally can be substituted. Typical examples are acetamido, a-ethylpropanamido, N-phenylacetamido, dodecanamido, 2,4-di-tert-amylphenoxyacetamido or α -3-tert-butyl-4-hydroxyphenoxybutanamido groups.

The sulfonamido groups represented by R are, for example, optional substituted alkylsulfonylamino or arylsulfonylamino groups. Typical examples these are methylsulfonylamino, pentadecylsulfonylamino, benzenesulfonamido, p-toluenesulfonamido and 2-methoxy-5-tert-amylbenzenesulfonamido groups.

The imido groups represented by R can be open-chain or cyclic and optionally substituted. At- games for this are Succinic acid imido, 3-heptadecyl succinic acid imido, phthalic acid imido or glutaric acid imido groups.

The ureido groups which can be represented by R can be alkyl or aryl, preferably be phenyl substituted. Examples are N-ethylureido, N-methyl-N-decylureido, N-phenylureido and N-p-tolylureido groups.

The sulfamoylamino groups which can be represented by R can be alkyl or aryl, preferably phenyl substituted. Examples are N, N-dibutylsulfamoylamino, N-methylsulfamoylamino or N-phenylsulfamoylamino groups.

The alkoxycarbonylamino groups which can be represented by R can optionally be substituted. Examples are methoxycarbonylamino, methoxyethoxycarbonylamino- and octadecyloxycarbonylamino groups.

The aryloxycarbonylamino groups which can be represented by R can optionally be substituted. Examples are phenoxycarbonylamino and 4-methylphenoxycarbonylamino groups.

The alkoxycarbonyl groups which can be represented by R can optionally be substituted. Examples are methoxycarbonyl, butyloxycarbonyl, dodecyloxycarbonyl, Octadecyloxycarbonyl, ethoxymethoxycarbonyloxy or benzyloxycarbonyl groups.

The aryloxycarbonyl groups which can be represented by R can optionally be substituted. Examples are phenoxycarbonyl, p-chlorophenoxycarbonyl and m-pentadecyloxyphenoxycarbonyl groups.

The alkylthio groups which can be represented by R can optionally be substituted be. Examples are ethylthio, dodecylthio, octadecylthio, phenethylthio and 3-phenoxypropylthio groups.

The arylthio group which can be represented by R preferably consists of one optionally substituted phenylthio group. Examples are phenylthio, p-methoxyphenylthio-, 2-tert-octylphenylthio-, 3-octadecylphenylthio-, 2-carboxyphenylthio- and p-acetaminophenylthio groups.

The heterocyclic thio groups representable by R are preferred 5- to 7-membered heterocyclic thio groups which fused onto a ring and / or may contain a substituent. Examples are 2-pyridylthio, 2-benzothiazolylthio and 2,4-diphenoxy-1,3,5-triazole-6-thio groups.

For those that can be represented by X and by reaction with the oxidation products substituents that can be split off from a color developer compound are groups which is substituted via a carbon, oxygen, sulfur or nitrogen atom are or halogen atoms, such as chlorine, bromine or fluorine atoms.

Groups substituted via a carbon atom are, for example, carboxyl groups and also groups of the formula: wherein R1 has the meaning given for R, Z 'has the meaning given for Z and R2 and R3 represent a hydrogen atom, an aryl group, an alkyl group or a heterocyclic group, or a hydroxymethyl or triphenylmethyl group.

Groups substituted via an oxygen atom are, for example Alkoxy, aryloxy, heterocyclic oxy, acyloxy, sulfonyloxy, alkoxycarbonyloxy, Aryloxycarbonyloxy, alkyloxalyloxy and alkoxyoxalyloxy groups.

The alkoxy groups can optionally be substituted and, for example from ethoxy, 2-phenoxyethoxy, 2-cyanoethoxy, phenethyloxy and p-chlorobenzyloxy groups exist.

Of the optionally substituted aryloxy groups, the optionally substituted phenoxy group preferred. Examples of such aryloxy groups are Phenoxy, 3-methylphenoxy, 3-dodecylphenoxy, 4-methanesulfonamidophenoxy, 4 - [# - (3'-pentadecylphenoxy) butanamido] phenoxy, Hexyldecylphenoxy, carbamoylphenoxyphenoxy, 4-cyanophenoxy, 4-methanesulfonylphenoxy, 1-naphthyloxyphenoxy and p-methoxyphenoxy groups.

The heterocyclic oxy groups are preferably optionally substituted 5- to 7-membered heterocyclic oxy groups. Examples these are 1-phenyltetrazolyloxy and 2-benzothiazolyloxy groups.

Acyloxy groups are, for example, alkylcarbonyloxy groups, such as acetoxy and butanoloxy groups, alkenylcarbonyloxy groups such as a cinnamoyloxy group, as Arylcarbonyloxy groups such as a benzoyloxy group.

Sulfonyloxy groups are, for example, butanesulfonyloxy and methanesulfonyloxy groups.

Alkoxycarbonyloxy groups are, for example, ethoxycarbonyloxy and Benzyloxycarbonyloxy groups.

An aryloxycarbonyl group is, for example, the phenoxycarbonyloxy group.

An example of the alkyloxalyloxy groups is the methyloxalyloxy group An example of the alkoxyoxalyloxy groups is the ethoxyoxalyloxy group.

Groups substituted via a sulfur atom are, for example, alkylthio, Arylthio, heterocyclic thio and alkyloxythiocarbonylthio groups.

Alkylthio groups are, for example, butylthio, 2-cyanoethylthio, Phenethylthio and benzylthio groups.

Arylthio groups are, for example, phenylthio, 4-methanesulfonamidophenylthio, 4-dodecylphenethylthio-, 4-nonafluoropentaamidophenethylthio-, 4-carboxyphenylthio- and 2-ethoxy-5-tert-butylphenylthio groups.

Heterocyclic thio groups are, for example, 1-phenyl-1,2,3,4-tetrazolyl-5-thio- and 2-benzothiazolylthio groups.

An example of the alkyloxythiocarbonylthio groups is the dodecyloxythiocarbonylthio group.

Groups substituted via a nitrogen atom are, for example, those of the formula: wherein R4 and R5 ', which may be the same or different, individually each represent a hydrogen atom or an alkyl, aryl, heterocyclic, sulfamoyl, carbamoyl, acyl, sulfonyl, aryloxycarbonyl or alkoxycarbonyl group and together form a heterocyclic ring can, with the proviso that R4 'and R5' do not simultaneously have the meaning of hydrogen atoms.

The alkyl groups are straight or branched chain Alkyl groups with preferably 1 to 22 carbon atom (s). These can be replaced by substituents, such as aryl, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, arylamino, acylamino, Sulfonamido, imino, acyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl, Alkoxycarbonyl, aryloxycarbonyl, alkyloxycarbonylamino, aryloxycarbonylamino, Hydroxyl, carboxyl and cyano groups and halogen atoms can be substituted. Typical Examples of such alkyl groups are ethyl, 2-ethylhexyl and 2-chloroethyl groups.

The aryl groups represented by R4 'and R5' expediently have 6 - 32 carbon atoms and consist in particular of phenyl or naphthyl groups.

The aryl groups in question can be substituted by substituents such as those for the alkyl groups representable by R4 'and R5' are indicated, and alkyl groups substituted be. Typical examples of such aryl groups are Phenyl, 1-naphthyl and 4-methylsulfonylphenyl groups.

These are preferably those that can be represented by R4 'and R5 heterocyclic groups to 5- or 6-membered heterocyclic groups that have a have fused-on ring and / or can be substituted.

Typical examples of such groups are 2-furyl, 2-quinolyl, 2-pyrimidyl, 2-benzothiazolyl and 2-pyridyl groups.

The sulfamoyl groups representable by R4 'and R5' are, for example N-alkylsulfamoyl, N, N-dialkylsulfamoyl, N-arylsulfamoyl and N, N-diarylsulfamoyl groups, their alkyl and aryl parts by the substituents mentioned for the alkyl and aryl groups can be substituted. Typical examples of such sulfamoyl groups are N, N-diethylsulfamoyl, N-methylsulfamoyl, N-dodecylsulfamoyl, and N-p-tolylsulfamoyl groups.

The carbamoyl groups represented by R4 'and R5' are, for example N-alkylcarbamoyl, N, N-dialkylcarbamoyl, N-arylcarbamoyl and N, N-diarylcarbamoyl groups, their alkyl and aryl parts by those given for the alkyl and aryl groups Substituents can be substituted. Typical examples of such carbamoyl groups are N, N-diethylcarbamoyl, N-methylcarbamoyl, N-dodecylcarbamoyl, N-p-cyanophenylcarbamoyl and N-p-tolylcarbamoyl groups.

The acyl groups represented by R4 'and R5' are, for example Alkylcarbonyl, arylcarbonyl and heterocyclic carbonyl groups, their alkyl, Aryl and heterocyclic parts can be substituted. Typical Examples for such acyl groups are hexafluorobutanoyl, 2,3,4,5,6-pentafluorobenzoyl, acetyl, Benzoyl, naphthoyl and 2-furylcarbonyl groups.

The sulfonyl groups represented by R4 and R5 can, for example optionally substituted alkylsulfonyl, arylsulfonyl or heterocyclic ones Be sulfonyl groups. Typical examples of such sulfony groups are ethanesulfonyl, Benzenesulfonyl, octanesulfonyl, naphthalenesulfonyl and p-chlorobenzenesulfonyl groups.

The aryloxycarbonyl groups represented by R4 'and R5' can be substituted in the manner indicated for the aryl groups. Case in point this is the phenoxycarbonyl group.

The alkoxycarbonyl groups represented by R4 and R5 can be in be substituted in the manner indicated for the alkyl group. Typical examples these include methoxycarbonyl, dodecyloxycarbonyl and benzyloxycarbonyl groups.

They are preferably those formed by R4 and R5 together heterocyclic rings around 5- or 6-membered heterocyclic rings, the more saturated or unsaturated, i.e. non-aromatic or aromatic in nature and condensed May contain rings.

Examples of the radicals of such heterocyclic rings are N-phthalimido, N-succinimido-, 4-N-urazolyl-, 1-N-hydantoinyl-, 3-N-2,4-dioxooxazolidinyl-, 2-N-1,1-dioxo-3- (2H) -oxo-1, 2-benzothiazolyl-, 1-pyrrolyl, 1-pyrrolidinyl, 1-pyrazolyl, 1-pyrazolidinyl, 1-piperidinyl, 1-pyrrolinyl, 1-imidazolyl, 1-imidazolinyl, 1-indolyl, 1-isoindolinyl, 2-isoindolyl, 2-isoindolinyl, 1-benzotriazolyl-, 1-benzoimidazolyl-, 1- (1,2,4-triazolyl) -1, 1- (1,2,3-triazolyl) -, 1- (1,2,3,4-tetrazolyl), N-morpholinyl, 1,2,3,4-tetrahydroquinolyl, 2-oxo-1-pyrrolidinyl, 2-1H-pyridone and 2-oxo-1-piperidinyl groups. These heterocyclic groups can alkyl, aryl, alkyloxy, aryloxy, acyl, sulfonyl, alkylamino, arylamino, acylamino, sulfonamino, carbamoyl, sulfamoyl, alkylthio, arylthio, ureido, alkoxycarbonyl, aryloxycarbonyl, imido, nitro, cyano, carboxyl or halogen substituted.

The nitrogen-containing heterocyclic ones to be completed by Z or Z ' Rings are, for example, pyrazole, imidazole, triazole or tetrazole rings. These can be substituted by the same substituents as are given for the radicals R. be.

In the event that a substituent such as R or one of the radicals R1 to R8 on a heterocyclic ring corresponding to formula (I) and formulas (II) to (VIII) has the following part: where R ", X and Z" have the same meaning as R, X and Z in formula (I), a so-called bis-type coupler is formed. Of course, such couplers also fall within the scope of the invention.

Furthermore, one can be completed by Z, Z ', Z "or Z 1 Ring another ring, e.g. a 5- to 7-membered cycloalkene ring fused on be.

In formula (VI), R7 and R8 together can have a 5- to 7-membered structure Complete the ring.

The magenta couplers that can be represented by the formula (I) can also typically be represented by the following formulas: In the formulas (II) to (VII) the radicals R1 to R8 and X correspond to the radicals X in formula (I).

Preferred couplers of the formula (I) are those of the formula (VIII) wherein R1, X and Z1 have the meanings of R, X and Z in formula (I).

Particularly preferred magenta couplers of the formulas (II) to (VII) are those of the formula (II).

A substituent on the heterocyclic rings of the formulas (I) to (VIII) is preferred when R in formula (I) or R1 in formulas (II) to (VIII) satisfies the following requirement 1. This substituent is particularly preferred when R or R1 fulfills the two requirements 1 and 2. The best results is achieved when with the substituent in question R or R1 the requirements 1, 2 and 3 is sufficient: Requirement 1: A directly to a heterocyclic Ring bonded atom is a carbon atom; Requirement 2: Only one hydrogen atom is attached to the carbon atom or nothing is attached to it; requirement 3: Any bond of the carbon atom to the neighboring atoms is a single bond.

The preferred substituents R and R1 on the heterocyclic rings mentioned are those of the formula: wherein R9, R10 and R11, which can be the same or different, each represent a hydrogen or halogen atom, or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclic, acyl, sulfonyl, sulfinyl -, sulfonyl, carbamoyl, sulfamoyl or cyano group, the residual group of a spiro compound or a crosslinked hydrocarbon compound, an alkoxy, aryloxy, heterocyclic oxy, siloxy, acyloxy, carbamoyloxy, amino, acylamino, sulfonamido , Imido, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, alkylthio or aryloxycarbonyl, or heterocyclic thio group, or R11 and R10 mean that at least two of the R10s are are different from hydrogen.

Two of the mentioned radicals R9, R10 and R11, e.g. the radicals R9 and R11 may with each other or together form a saturated or unsaturated ring, e.g. form a cycloalkane or cycloalkene ring or a heterocyclic ring, or furthermore, by coupling R11 to the relevant ring, the remainder of a cross-linked group Form hydrocarbon compound or a bridging hydrocarbon compound.

The groups which can be represented by R9 to R11 can be substituted. Typical examples of the radicals R9 to R11 and their substituents are related named with formula (I) for R and the substitute.

Typical examples of rings that can be represented by R9 and R10 and crosslinked hydrocarbon compounds which can be represented by R9 to R11 as well for substituents for the radicals R9 to R11 are those in connection with formula (I) for R mentioned cycloalkyl and cycloalkenyl groups, heterocyclic groups and Residual groups of crosslinked hydrocarbon compounds and their substituents.

With regard to formula (IX), the following two cases are preferred: 1. Two of the radicals R9 to R11 are alkyl groups and 2. one of the radicals R9 to R11 represents a hydrogen atom and the other two radicals, e.g. R10 and R11, form together with the carbon atom (to which they are attached) a cycloalkyl group.

In case 1), two of the radicals R9 to R11 should preferably be alkyl groups represent and the third radical represent a hydrogen atom or an alkyl group.

The alkyl and cycloalkyl groups mentioned can optionally be substituted be. Typical examples of the alkyl groups, cycloalkyl groups and their substituents are the alkyl groups, cycloalkyl groups specified for R in connection with formula (I) and their substituents.

As substituents for those represented by Z in formula (I) or

Z1 in formula (VIII) completed rings and as radicals R2 bis R8 in formulas (II) to (VI) are radicals of the formula: -R¹-SO2-R² (X) wherein R1 represents an alkylene group and R2 represents an alkyl, cycloalkyl or aryl group, preferred.

The alkylene group which can be represented by R1 can be straight-chain or branched and should preferably not be less than 2, in particular, in its straight chain part 3 to 6 carbon atoms. Optionally, the alkylene group can also be substituted.

Examples of such substituents are corresponding to alkyl groups the meaning of R in formula (X).

The preferred substituent is, for example, a phenyl group.

Typical and preferred examples of alkylene groups which can be represented by R R1 are those of the formulas: The alkyl group which can be represented by R2 can be straight-chain or branched.

Examples of such alkyl groups are methyl, ethyl, propyl, isopropyl, Butyl, 2-ethylhexyl, octyl, dodecyl, tetradecyl, hexadecyl, octadecyl and 2-hexyldecyl groups.

The cycloalkyl groups which can be represented by R² are preferably 5- or 6-part. An example of this is the cyclohexyl group.

The alkyl and cycloalkyl groups represented by R2 can be substituted be. Examples of suitable substituents are given for the radical R1.

Typical examples of aryl groups that can be represented by R2 are phenyl and naphthyl groups. The aryl groups in question can be substituted. Examples for substituents are straight or branched chain alkyl groups and next to them the substituents mentioned for R1.

If at least two substituents are present, these can be the same or be different.

Particularly preferred compounds of the formula (I) correspond to the formula: wherein R and X have the meanings of R and X in formula (I) and R1 and R2 have the meanings of R1 and R² in formula (X).

Typical examples of magenta couplers which can be used according to the invention are given below: The typical couplers given as examples can be according to those known from "Journal of the Chemical Society", Perkin I, 1977, pp. 2047-2052, US Pat. No. 3,725,067 and JP-OSes 99437/1984 and 42045/1983 Process.

The couplers which can be used according to the invention arrive in an amount in each case based on 1 mole of silver halide, expediently from 1 x 10-³ to 1, preferably 1 x 10-² to 8 x 10-¹ mol is used.

The couplers which can be used according to the invention can also be used together with other types of magenta couplers can be used.

The term "one combined with a silver halide emulsion layer Magenta coupler "or" a coupler associated with a silver halide emulsion layer " means a magenta coupler which reacts with those upon color development oxidation products of a color developing agent formed on the silver halide emulsion layer capable of producing a purple dye image.

The following are monodisperse emulsions which can be used according to the invention explained in more detail.

A monodisperse emulsion is understood to be one with a coefficient of variation of not more than 0.22, preferably not more than 0.15, for the grain size distribution of a silver halide contained in the emulsion. The coefficient of variation indicates the extent of the grain size distribution and is calculated from the following equations: Variation standard deviation of the grain size coefficient = division (S / r) Average grain size Standard deviation of the grain size distribution (S) mean grain size (r) = In the equations, ri is the grain size of the individual grains and ni is their number.

The term grain size denotes the diameter of a grain, if it is spherical silver halide. It also means the diameter a circular image of the same area as the projected grain image, if the grain is other than spherical in shape.

Monodisperse emulsions which can be used according to the invention can be used alone or can be used in combination or in a mixture, provided it is ensured that that the coefficient of variation of the combination or mixture is not more than 0.22 amounts to. Mixtures of polydisperse and monodisperse emulsions can also be used bring to use. Monodisperse emulsions preferably used according to the invention single species or mixtures of no more than three species are more monodisperse Emulsions with each because a coefficient of variation of not more than 0.22, or a mixture of a polydisperse emulsion and a monodisperse Emulsion. In the case of the mixture mentioned, the monodisperse emulsion has a smaller average grain size than the polydisperse emulsion and does not increase less than 40% of the total projected area of all silver halide grains a. The monodisperse emulsion which can be used according to the invention preferably consists from a single type of monodisperse emulsion with the specified coefficient of variation of not more than 0.22 or a mixture of two such emulsions.

The average grain size defined by the formula given of the silver halide grains contained in the monodisperse emulsions which can be used according to the invention should expediently at least 0.25 to at most 0.75, preferably at least 0.35 to a maximum of 0.65 µm.

Regarding the silver halide composition according to the invention There are no specific silver halide grains that can be used for emulsions Limitation.

Preferably, however, the silver iodide content should be low, i. the emulsion should be essentially a silver chlorobromide emulsion Act. This is to be understood as meaning a silver chlorobromide emulsion, its silver halide less than 1 mol% of silver iodide and the remainder of silver chloride and silver bromide consists.

In such silver halide grains, the silver chloride content should be expediently not less than 5 mol%, preferably not less than 15 mol%, be.

The monodisperse emulsions which can be used according to the invention sions silver halide grains contained may have any crystal habit. So can any regular or irregular shaped crystals including spherical or plate-shaped crystals are used. Are usable for example crystals with any ratio of the [100] plane to the [111l plane yee.e. In addition, mixed crystal forms and mixtures of different Crystal forms can be used.

The silver halide grains usable in emulsions usable in the present invention can be produced by the acid, neutral and ammonia process. You can grown at the time of or after the production of seed crystals. The measures for preparing the seed crystals and for letting them grow can be the same or different from one another.

Process for reacting a soluble silver salt with a soluble one Halide are, for example, the normal precipitation process (or single beam precipitation process), the reverse felling method, the double beam felling method, combinations of the same and the same. For reasons of reaction, the double jet precipitation method is preferred. In order to improve monodispersibility, one embodiment of the above should be used Double jet method known from JP-OS 48521/1979 and controlled with pAg value carried out double jet precipitation method are used.

If necessary, solvents for silver halides, e.g. Thioethers, or control substances for the crystal habit, e.g. compounds with mercapto groups, as well as spectral sensitizing dyes can also be used.

In the course of the formation and / or the growth of the in the invention used monodisperse emulsions can be used silver halide grains Metal ions are added and into the interior and / or in the surface area of the granules to be built in. This is done, for example, with the help of cadmium, zinc, lead, Barium or iridium salts or complex salts thereof, rhodium salts or complex salts the same or iron salts or complex salts thereof. If you put the granules in Spends a suitable reducing atmosphere inside and / or inside Surface area thereof can also be created with reduction sensitization spots.

From the emulsions which can be used according to the invention, after completion the growth of the silver halide grains also removes unnecessary soluble salts will. On the other hand, these superfluous soluble salts can also be found in the emulsions remain. If they are removed, this can be done according to "Research Disclosure", Volume 17643, happen.

The silver halide grains contained in emulsions which can be used in the present invention from their surface to the grain inner can be the same or from different layers be constructed.

Silver halide grains useful in emulsions usable in the present invention can depict a latent image primarily on their surface or inside the grain.

The emulsions which can be used according to the invention are more commonly known Way chemically sensitized. Sensitization is done, for example, through Sulfur sensitization by means of a sulfur-containing substance that is reactive with silver ions Connection and an active Gelatin, by selenium sensitization by means of a selenium compound, by reduction sensitization by means of a reducing Substance or by noble metal sensitization by means of a gold compound or any other precious metal compound. The procedures mentioned can be used individually or be carried out in combination.

The emulsions which can be used according to the invention can be used for the desired Wavelength range with the help of known spectral ranges commonly used in photography Sensitizing dyes are spectrally sensitized.

These spectral sensitizing dyes can be used alone or in Combination get used. Furthermore, those which can be used according to the invention can be used Emulsions in addition to the spectral sensitizing dyes also dyes without their own spectral sensitization effect or supersensitizers, i.e. Compounds that practically do not absorb even visible light, however increase the sensitizing effect of the spectral sensitizing dyes, contain.

To make the photosensitive recording material anti-fogging and / or to the photographic properties of the recording material during to keep them stable during manufacture, storage and / or photographic processing, can be used for the emulsions which can be used according to the invention Antifoggants and / or stabilizers are incorporated.

This can be at any time during and / or after the chemical sensitization, but before applying the silver halide emulsion, take place.

"Light-sensitive color photographic recording materials too "Copying" means light-sensitive color photographic material intended for direct viewing On- drawing materials. Consequently, their supports are not limited to paper only. Suitable as a support for such recording materials for example baryta paper, paper backing laminated with polyolefin resins, polyethylene terephthalate support containing white pigment; and transparencies Film support with a hydrophilic colloid layer applied thereon, in which is a white pigment dispersed. Preferred supports according to the invention Recording materials are white in color. Such are in detail, for example paper backing laminated with a polyolefin resin, which is in the polyolefin layer contain a white pigment such as anatase-type titanium dioxide incorporated therein, and a polyethylene terephthalate film containing a white pigment such as barium sulfate.

The reasons why the success that can be achieved according to the invention is significant Dimension only for light-sensitive color photographic ones suitable for copying purposes Recording materials with reflective substrates of the specified type comes into play have not yet been fully clarified. Probably playing here optical or psychological reasons play a role. Such reasons can be induced thereby become that a white support for viewing a color photograph directly used with reflected light. There is also a physiological reason conceivable, since the purple color stands out clearly compared to the other colors, i.e.

the spectral luminosity of the purple color is high.

Other reasons are also conceivable. Nonetheless, there So far there has been no clear explanation for the success that can be achieved according to the invention.

As binders or protective colloids according to the invention Recording materials come in particular gelatin and also gelatin derivatives, graft polymers of gelatine and other macromolecular substances, proteins, sugar derivatives, Cellulose derivatives and hydrophilic colloids, e.g. by mono- or copolymerization synthesized hydrophilic macromolecular substances in question.

In the case of recording materials according to the invention, the photographic Emulsion layers and the other hydrophilic colloid layers by crosslinking of binding agent or protective colloid molecules and / or through the use of hardening agents Hardened to strengthen the layer strength. Preferably one should Hardening agents are added in such an amount that to harden the photosensitive No further hardener added to the recording material in a treatment bath must become. Of course, such hardeners can also use the various Treatment baths are added.

To improve the flexibility of the individual layers, a recording material according to the invention the silver halide emulsion layers and / or incorporated plasticizers into the other hydrophilic colloid layers will.

Furthermore, in a recording material according to the invention both the photographic emulsion layers and the other hydrophilic ones Colloid layers insoluble or hardly soluble synthetic polymers (as latex) dispersed included, to the dimensional stability of the concerned Improve layers.

A recording material according to the invention is color-developed, by coupling reaction contained therein tener, dye-forming Couplers with the oxidation products of primary aromatic amine color developing agents, e.g. from p-phenylenediamine or aminophenol derivatives, dyes are formed. Usually, dye-forming couplers are chosen for this purpose, with the aid of which they are used corresponding to the spectral absorption capacity of the various emulsion layers Dyes are formed. This is particularly the case in blue-sensitive emulsion layers Yellow couplers, magenta couplers in green-sensitive emulsion layers, and red-sensitive ones Emulsion layers housed cyan couplers.

Depending on the desired goal, differently combined emulsion layers can also be used provide.

Suitable yellow couplers are, for example, acylacetamide couplers, such as Benzoylacetanilide or pivaloylacetanilide couplers; are suitable magenta couplers for example 5-pyrazolone, pyrazolobenzimidazole, pyrazolotriazole and open-chain Acylacetonitrile coupler; suitable cyan couplers are, for example, naphthol and phenolic couplers.

Yellow couplers are, for example, 4- or 2-equivalent couplers of the acylacetamide type or benzoyl methane type (cf.

U.S. Patents 2,186,849, 2,322,027, 2,728,658, 2,875,057, 3,265,506, 3,277 155, 3 408 194, 3 415 652, 3 447 928, 3 664 841, 3 770 446, 3 778 277, 3 849 140 and 3,894,875, British Patents 778,089, 808,276, 875,476, 1,402,511, 1,421,126 and 1,513 832 and JP-OSes 13576/1974, 29432/1973, 66834/1973, 10736/1974, 122335/1974, 28834/1975, 132926/1975, 138832/1975, 3631/1976, 17438/1976, 26038/1976, 26039/1976, 50734/1976, 53825/1976, 75521/1976, 89728/1976, 102636/1976, 107137/1976, 117031/1976, 122439/1976, 143319/1976, 9529/1978, 82332/1978, 135625/1978, 145619/1978, 23528/1979, 48541/1979, 65035/1979, 133329/1979 and 598/1980.

Cyan couplers are, for example, 4 or 2 equivalent cyan couplers of the phenol or naphthol type (cf.

e.g. U.S. Patents 2,306,410, 2,356,475, 2,362,598, 2,367,531, 2,369,929, 2,423,730, 2,474,293, 2,476,008, 2,498,466, 2,545,687, 2,728,660, 2,772 162, 2 895 826, 2 976 146, 3 002 836, 3 419 390, 3 446 622, 3 476 563, 3 737 316, 3 758 308 and 3 839 044, GB-PSs 478 991, 945 542, 1 084 480, 1 377 233, 1 388 024 and 1 543 040 and JP-OSes 37425/1972, 10135/1975, 25228/1975, 112038/1975, 117422/1975, 130441/1975, 6551/1976, 37647 / 19i6, 52828/1976, 108841/1976, 109630/1978, 48237/1979, 66129/1979, 131931/1979 and 32071/1980.

The said color couplers should expediently be in their molecules sucked Contain ballast groups with no fewer than 8 carbon atoms each, so that they become diffusion-proof.

As already mentioned, the color couplers mentioned can be used to form of a dye molecule from so-called. 4-equivalent couplers (in which four silver ions are reduced) or 2-equivalent couplers (in which two silver ions are reduced will exist. The 2-equivalent couplers are particularly preferred.

For the hydrophobic color couplers that are not on the surfaces of the If silver halide crystals have to be adsorbed, a solid dispersion process can be used, a latex dispersion method, an oil droplet-in-water emulsion dispersion method and other procedures. Depending on the chemical structure and the like of this hydrophobic couplers are selected from these methods suitable the end. With the Ötrapfchen-in-water-emulsion -dispersing process, the hydrophobic Coupler converted into a suitable and reusable dispersion. To this The purpose of the hydrophobic coupler is usually in a high-boiling organic Solvent with a boiling point not lower than 1500C (if necessary in combination with a low-boiling solvent and / or a water-soluble one organic solvent). The resulting solution is then used together with a hydrophilic binder, e.g., an aqueous gelatin solution with a surface-active one Means, with the help of a stirrer, homogenizer, colloid mill, flow jet mixer, an ultrasonic device and the like are emulsified and dispersed. The The emulsified and dispersed material is then deposited directly into a hydrophilic colloid layer incorporated.

For the magenta couplers of the formula (I) which can be used according to the invention should preferably be compounds with as high-boiling organic solvents dielectric constant less than 6.0 can be used. The lower limit for the dielectric constant (of the high-boiling solvents) is not special critical, but preferably not less than 1.9. Preferred High-boiling solvents are esters, e.g. phthalic and phosphoric acid esters, organic Acid amides, ketones, hydrocarbon compounds and the like each having one Dielectric constant less than 6.0. Preferred high-boiling solvents are the phthalic or phosphoric acid esters. The organic solvents mentioned can can also be used as a mixture of two or more; in this case it should the dielectric constant of the mixture is preferably less than 6.0. The information regarding the di- constant of electricity relate to values determined at 30 ° C. Examples of high-boiling points which can be used according to the invention organic solvents are dibutyl phthalate, dimethyl phthalate, tricresyl phosphate and tributyl phosphate.

The phthalic esters which can be used advantageously according to the invention correspond to the formula: wherein R12 and R13, which can be the same or different, each represent an alkyl, alkenyl or aryl group, with the proviso that the total number of carbon atoms is 9-32, preferably 16-24.

Examples of representable by R12 or R13 in the formula (XII) Alkyl groups are straight and branched chain alkyl groups, such as butyl, pentyl, Hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl-tetradecyl, Pentadecyl, hexadecyl, heptadecyl and octadecyl groups. Those by R12 or R13 Aryl groups which can be represented in formula (XII) are, for example, phenyl and naphthyl groups. The alkenyl groups that can be represented by the radicals mentioned are, for example, hexenyl, Heptenyl and octadecenyl groups. These alkyl, alkenyl and aryl groups can be or contain several substituents. Examples of substituents of the alkyl and Alkenyl groups are halogen atoms and also alkoxy, aryl, aryloxy, alkenyl and alkoxycarbonyl groups. Substituents for the aryl groups are, for example, halogen atoms as Alkyl, alkoxy, aryl, aryloxy, alkenyl and alkoxycarbonyl groups. In the alkyl, Alkenyl or aryl groups can also be introduced with more than two substituents.

The phosphoric acid esters which can be used according to the invention correspond to the formula: wherein R14, R15 and R16, which can be the same or different, each represent alkyl, alkenyl or aryl groups, with the proviso that the total number of carbon atoms is 24 to 54.

Alkyl groups which can be represented by R14, R15 and R16 are, for example Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, Tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl and nonadecyl groups. Aryl groups that can be represented by these radicals are, for example, phenyl and naphthyl groups. Alkenyl groups that can be represented by these radicals are, for example, hexenyl, heptenyl and octadecenyl groups.

These alkyl, alkenyl and aryl groups can have one or more substituents contain. R14, R15 and R16 are preferably alkyl groups, such as 2-ethylhexyl, n-octyl, 3,5,5-trimethylhexyl, n-nonyl, n-decyl, sec-decyl and tert-octyl groups.

Typical examples of preferred organic solvents are: When dissolving hydrophobic compounds in a low-boiling solvent or in a mixture of low-boiling and high-boiling solvents, an anionic, nonionic or cationic wetting agent can also be used as a dispersant. The solution obtained in this way can be dispersed mechanically or with the aid of ultrasonic waves.

Recording materials according to the invention can be used to prevent color contamination, impairment of sharpness and coarsening of the grain, caused by migration of the oxidation products or of electron-transferring components a developer compound between the emulsion layers, namely between layers same color sensitivity and / or different color sensitivity contain paint retardants.

The color haze retardants can be used in the emulsion layers themselves or in intermediate layers provided between adjacent (emulsion) layers be housed.

In order to prevent impairment of the color image, recording materials according to the invention preferably contain image stabilizers, for example those of the following formulas (A) to (H) and (J) to (K): In the formula (A): R1 denotes a hydrogen atom or an alkyl, alkenyl, aryl or heterocyclic group; R2, R3, R5 and R6, which can be the same or different, each represent a hydrogen or halogen atom or a hydroxyl, alkyl, alkenyl, aryl, alkoxy or acylamino group and R4 an alkyl, hydroxy, aryl or alkoxy group.

R1 and R2 together can complete a 5- or 6-membered ring. When this is the case, R4 is a hydroxy or alkoxy group. Also R3 and R4 together can complete a 5-membered hydrocarbon ring. if this is the case, R1 stands for an alkyl, aryl or heterocyclic group, with the proviso, however, that R1 is not hydrogen and R4 is a hydroxyl group represents.

As already mentioned, R1 in formula (A) stands for a hydrogen atom or an alkyl, alkenyl, aryl or heterocyclic group. Examples of alkyl groups are straight or branched chain alkyl groups, such as methyl, ethyl, propyl, n-octyl, tert-octyl or hexadecyl groups. Alkenyl groups that can be represented by R1 are allyl, Hexenyl or octenyl groups. Aryl groups which can be represented by R1 are, for example Phenyl or naphthyl groups.

Heterocyclic groups which can be represented by R1 are, for example Tetrahydropyranyl or pyrimidyl groups. The groups mentioned can be substituted be. Examples of substituted alkyl groups are benzyl or ethoxymethyl groups. Examples of substituted aryl groups are methoxyphenyl, chlorophenyl and 4-hydroxy-3,5-dibutylphenyl groups.

In the formula (A), as already mentioned, R2, R3, R5 and R6 stand for Hydrogen or halogen atoms or hydroxy, Alkyl, alkenyl, Aryl, alkoxy or acylamino groups.

Examples of such alkyl, alkenyl or aryl groups are the groups mentioned in connection with R1. Examples of halogen atoms are Fluorine, chlorine and bromine atoms. Examples of alkoxy groups are methoxy and ethoxy groups. Acylamino groups are those of the formula R'CONH-, where R 'is an alkyl group, e.g. a methyl, ethyl, n-propyl, n-butyl, n-octyl, tert-octyl or benzyl group, an alkenyl group such as an allyl, octenyl or oleyl group, an aryl group, e.g.

a phenyl, methoxyphenyl or naphthyl group, or a heterocyclic group Group such as a pyridyl or pyrimidyl group.

In the formula (A), as already mentioned, R4 stands for an alkyl, Hydroxy, aryl or alkoxy group. As examples of alkyl or aryl groups, the groups mentioned in connection with R1 are listed. Examples of through R4 representable alkoxy groups can be found in the explanation of R2, R3, R5 and R6.

R1 and R can complete a ring fused to the benzene ring. Such rings are, for example, chroman, coumaran or methylenedioxybenzene rings.

R3 and R4 together can fused onto the benzene ring Complete the ring. Such a ring is, for example, the indan ring. The mentioned Rings can be, for example, alkyl, alkoxy or aryl substituted.

The ring systems to be formed by R1 and R2 or R3 and R4 can also contain spiro atoms with the formation of spiro compounds. R2, R4 and the like. can also represent linking groups with the formation of bis-substances.

The preferred phenol or phenyl ether compounds of the formula (A) are the indone compounds each having four RO groups, in which R stands for an alkyl, alkenyl, aryl or heterocyclic group. Compounds of the formula: wherein R stands for an alkyl group, for example a methyl, ethyl, propyl, n-octyl, tert-octyl, benzyl or hexadecyl group, an alkenyl group, for example an allyl, octenyl or oleyl group, an aryl group, for example a phenyl or naphthyl group, or a heterocyclic group, for example a tetrahydropyranyl or pyrimidyl group.

R9 and R10, which can be the same or different, stand for Hydrogen or halogen atom, e.g. a fluorine, chlorine or bromine atom, an alkyl group, e.g. a methyl, ethyl, n-butyl or benzyl group, an alkenyl group e.g. an allyl, hexenyl or octenyl group, or an alkoxy group, e.g. a methoxy, Ethoxy or benzyloxy group.

R11 represents a hydrogen atom, an alkyl group, e.g.

a methyl, ethyl, n-butyl or benzyl group an alkenyl group, e.g. a 2-propenyl, hexenyl or octenyl group, or an aryl group e.g. Phenyl, methoxyphenyl, chlorophenyl or naphthyl group.

Compounds of formula (A) are disclosed in U.S. Patents 3,935,016, 3,982 944 and 4,254,216, Japanese Patent Nos. 21004/1980 and 145530/1979, British Patent Nos. 2,077,455 and 2,062,888, U.S. Patents 3,764,337, 3,432,330, 3,574,627, and 3,573,050, Japanese Patent Laid-Open 152225/1977, 20327/1978, 17729/1978 and 6321/1977, GB-PS 1,347,556, GB-OS 2,066,975, Japanese Patent Nos. 12337/1979 and 31625/1973, and U.S. Patent 3,700,455.

Based on the magenta coupler used, the amount is Compound (s) of the formula (A) expediently from 5 to 300, more preferably from 10 to 200, mol%.

Typical examples of compounds of the formula (A) are given below: TYPE (1) Compound- R¹ R² R³ R4 R5 R6 manure No. A-1 H OH -C (CH3) 2CH2C (CH3) 3 CH3O H -C (CH3) 2CH2C (CH3) 3 A-8 C @ H @@ C (CH3) 2C2H5 H C6H17O C (CH3) 2C2H5 H A-14 HH OH C (CH3) 2CH2C (CH3) 3 HH A-16 HC (CH3) 2C @ H7 H CH3O C (CH3) 2C @ H7 H Type (2) Compound- R¹ R² R³ R4 R5 R6 R7 R8 manure No. A-2 CH3 OH CH3 CH3 CH3 OH CH3 CH3 A-10 CH3 OCH3 CH3 CH3 CH3 CH3O CH3 CH3 Type (3) Iverbin- ! R 'R2 R3 R' R5 Rb auns No. n -3 i cri, cn, H Clf a (t) C s li 1 7 01 A-11 1 Cll C113 II C113 (t) c81117 C.1I170 A-12 i If C113 cn, C113 11 C113 C113 O (Cll2) 20C10ll21 A-17 jn Cll CII, C113 (t) C01117 011 5 011 From Cl13 C113 Cm13 i CII, olí 1 C113 i 011 Type (4) Connect- T Rl R2 manure No. A-4 C, H7 Ij C3II? > -CII20 (CH2) 20CH2 A-9 CH7 CH: O (C112) 2OC4Hs Type (5) Connect- R¹ R² R³ R4 R5 manure No. A-5 CH3 CH3 C2H5O (t) C @ H2 @ OH Type (6) Compound- R¹ R² R³ R4 R5 R6 R7 manure No. A-6 H (t) C4H9 CH3 CH3 (t) C4H9 H CH2 A-15 CH3 (t) C4H9 CH3 CH3 (t) C4H9 Ch3 CH2 TYPE (7) Compound- R¹ R² R³ R4 R5 R6 R7 R8 R9 R10 R11 R12 manure No. A-13 H C3H7O C3H7O CH3 CH3 HHH C3H2O C3H7O CH3 CH3 A-19 H CH3O CH3O CH3 CH3 HHH CH3O CH3O CH3 CH3 A-20 CH3 C4H @ O C1H @ O CH3 CH3 HH CH3 C4H9O C4H @ O CH3 CH3 A-21 H C2H5O C2H9O CH3 CH3 HHH C2H5O C2H5O CH3 CH3 A-22 H CH3O CH3O C2H5 CH3 H CH3 H CH3O CH @ O CH3 C2H5 A-23 H C7H15COO C7H15COO CH3 CH3 HHH C7H15COO C7H18COO CH3 CH2 A-24 H C4H2O C4H9O CH2 CH3 HHH C4H9O C4H9O CH3 CH3 A-25 H CH3O (CH2) 2O CH @ O (CH2) 2O CH3 CH3 HHH CH @ O (CH2) 2O CH3O (CH2) 2O CH3 CH3 A-26 H CH2 = CHCH2O CH2 = CHCH2O CH3 CH3 C @ H5 HH CH2 = CHCH2O CH2 = CHCH2O CH3 CH3 A-27 H C3H2O C3H7O C6H5CH2 CH3 HHH C3H7O C3H7O C6H5O CH3 A-28 CH3O C4H9O C4H9O CH3 CH3 HH CH3 C4H9O C4H9O CH3 CH3 A-29 H (s) C @ H11O (s) C5H11O CH3 CH3 HHH (s) C5H11O (s) C5H11O CH3 CH3 A-30 H C4H9O C4H9O (i) C3H2 CH3 CH3 CH3 H C4H9O C4H9O (i) C3H7 CH3 A-31 H C18H37O C18H37O CH3 CH3 HHH C18H37O C18H37O CH3 CH3 A-32 H C5H5CH2O C6H5CH2O CH3 CH3 HHH C6H5CH2O C6H5CH2O CH3 CH3 Formula (B): In the formula (B), R¹ and R4, which may be the same or different, each represent a hydrogen or halogen atom, or an alkyl, alkenyl, alkoxy, alkenyloxy, hydroxy, aryl, aryloxy, acyl , Acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxycarbonyl group, R2 is a hydrogen atom or an alkyl, alkenyl, aryl, acyl, cycloalkyl or heterocyclic group and R3 is a hydrogen or halogen atom or an alkyl, alkenyl group -, aryl, aryloxy, acyl, acyloxy, sulfonamido, cycloalkyl or alkoxycarbonyl group.

The groups mentioned can each be replaced by the other substituents be substituted. Examples of such substituents are alkyl, alkenyl, alkoxy, Aryl, aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, acyloxy, Carbamoyl, sulfonamido and sulfamoyl groups.

R2 and R3 together can complete a 5- or 6-membered ring. In this way, for example, chromane and methylenedioxybenzene rings can then be formed.

Y stands for one required for the formation of a chroman or coumaran ring Group of atoms.

These chroman or coumaran rings can be replaced by halogen atoms or alkyl, Cycloalkyl, alkoxy, alkenyl, alkenyloxy, hydroxy, aryl or aryloxy groups or heterocyclic rings can be substituted and form a spiral ring.

Particularly preferred compounds of the formula (B) are those of the formulas In the formulas (B-1) to (B-5) the radicals R1, R2, R3 and R4 correspond to the radicals R1, R2, R3 and R4 in the formula (B). The radicals R5, R6, R7, R8, R9 and R10, which can be identical or different, represent hydrogen or halogen atoms or alkyl, alkoxy, hydroxy, alkenyl, alkenyloxy, aryl, aryloxy or heterocyclic groups.

R5 and R6, R6 and R7, R7 and R8, R8 and R9 and R9 and R10, respectively complete carbon rings together. These carbon rings can get through Be substituted by alkyl groups.

Of the compounds of the formula (B-1) to (B-5), those preferably, in the case of R1 and R4, hydrogen atoms or alkyl, hydroxy or cycloalkyl groups and R5, R6, R71, R8, R9 and R10 represent hydrogen atoms or alkyl or Cycloalkyl groups.

The compounds of the formula (B) also include those from "Tetrahedron", 1970, Volume 126, Pages 4743-4751, "Journal of The Chemical Society of Japan", 1972, No. 10, pages 987-1990, "Chemical Letter", 1972, No. 4, pages 315-316, and of JP-OS 139383/1980 known and produced by the method described above Links.

Based on the magenta coupler (s) which can be used according to the invention the amount of compound (s) of the formula (B) is expediently 5-300, more preferably 10-200 mole percent.

Typical examples of compounds of the formula (B) are given below: Compound- R¹ R² R³ R4 R5 R6 R7 R8 R9 R10 application no. B-1 HHHHH CH3 HH CH3 CH3 B-2 HH CH3 HH CH3 HH CH3 CH3 B-3 HH C12H25 HH CH3 HH CH3 CH3 B-4 HH # HH CH3 HH CH3 CH3 B-5 H CH3 HHH CH3 HH CH3 CH3 B-9 CH3 H CH3 HHHH # (condenser- H sation) B-10 H CH @ CO HHH (i) C3H7 HH CH3 CH3 B-11 H C3H7 (t) C @ H17 HH CH3 H CH3 CH3 CH3 B-12 Br H Br HHHH CH3 CH3 CH3 B-13 H # HH CH3 CH3 HH CH2OH CH3 B-14 H # HH CH3 CH3 HH CH3 CH3 B-15 HH CH2 = CHCH2CO CH3 CH3 HH # CH2 B-16 HHH CH3SO2NH CH3 CH3 HH # CH3 B-17 H # CH3 H CQ H CQ H CH3 CH3 B-18 H # CH3CONH HHHHH # (Spiro) B-54 CH3O CH3O HHHHHH CH3 CH3 B-55 H # (methylenedioxy) HHHHH CH3 CH3 V & bin- R 'R2 R4 R5 R0 IVerbin- RS R 2 R3 R4 RS R6 R7 R8 manure no, B-6 l II II H fl Di HICKonaen- ii sation) 8-7 ii Ii HH (i) C3117 II Ii Ii Cll3 Cll3 B-8 IJ Cll3 C ca fl 1I CH3 Cll B-19 II Ii to II Cll3 C113 Cll3 Cll3 B-20 11 Cll2 = CllCII2 CII3 ii CH3 CII. C113 11 B-21 11 Cll Carl7 II Cl13 Cll3 4 11 8-22 CH3 ii .Cll3 HW (SPiro) II II B-23 CH3 1 O COO II C3 CH3 CII. C113 xTerbir.- R 'R2 R3 R R4 R5 R9 R'0 application no. B -24 li II 11 ii C113 Cll 3 ll ll B-25 11 11 C113 II Cl13 CH Ii 11 B -26 II H (t) C411s, 11 II II ii II B-27 II C113 II H C113 CII3 11 II B-28 Ii ii cll. CH3 H CII. CII. 11 II B-29 11 II C211sCOOC112 ii Cl13 C113 11 II B-30 CII. 5 CH2 H CH3 CII. C113 11 H. B-31 CQ II 11 (Spiro> II R B-32 11 CII CllaCONII ii cll3 CII. ii II B-33 CII. (t) CsllI? 11 CH3 CH3 11 ii D-34 H II O Cil 2- 11 Clla Clla HH Connect- nX R2 R3 R4 R5 R6 R R3 application no. B -35 II II Ii II Cl13 CH 3 Ii H D-36 11 C3117 Ii H Cll a C113 3 U II B-37 II Cli. Cit 3 11 Clla C113 H 11 B-38 HH (t) C4H H Cli. CH3 II H B-39 H II t3C} 13 CB3 CII. II HH B-40 11 II CU3SO2NII H II II HH D-41 C113 H CH3 CII. CH H II B-42 CQ (t) C4119 ii ii (Spiro) HB D-43 H Cl C121125 C11.CONfl H Cli. CII. HH B-44 11 H (t) CsHI? 7 H CII. ca3 HH B-45 11 II IHIH CII. II H Ii erbin- RI 1 <R5 R6 R7 R8 R9 R'O manure No. B-46 11 lI II II II Ii Cll a CII. B-47 011 II 11 11 II 11 CII. C113 H 11 HU II HH CH3 C2U5 B-49 II ii sR U li UW (Spiro) D-50 C3H70 II CH3 H Ii II Cii. Cli3 B-51 11 fl II Ii C3117 Ii C3117 II B-52 H 011 .HHHH CII. CII. B-53 II Sah70 II II II H CH3 CII.

Formula (C): Formula (D): In the formulas (C) and (D), R1 and R2, which can be identical or different, each represent a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, alkenyloxy, hydroxy, aryl, aryloxy -, acyl, ACylamino, acyloxy, sulfonamido or alkoxycarbonyl group.

The groups mentioned can be replaced by the other substituents in each case be substituted. Examples of such substituents are halogen atoms or alkyl, Alkenyl, alkoxy, aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, Carbamoyl, sulfonamido and sulfamoyl groups.

Y stands for that group of atoms which, together with the benzene ring to form a dichroman or Dicumaran rings required are.

The chroman or coumaran rings in question can be replaced by halogen atoms, Alkyl, cycloalkyl, alkoxy, alkenyl, alkenyloxy, hydroxy, aryl or aryloxy groups or heterocyclic groups can be substituted and form a spiral ring.

Of the compounds of the formulas (C) and (D), those of the following formulas are preferred: In the formulas (C-1), (C-2), (D-1) and (D-2) the radicals R1 and R2 have the meaning of the corresponding radicals in the formulas (C) and (D). R³, R4, R5, R6, R7 and R8, which can be identical or different, stand for hydrogen or halogen atoms or alkyl, alkoxy, hydroxy, alkenyl, alkenyloxy, aryl or aryloxy groups or heterocyclic groups. R3 and R4, R4 and R5, R5 and R6, R6 and R7 or R7 and R8 together can complete a carbon ring. These carbon rings can be substituted by alkyl groups.

Particularly suitable compounds of the formulas (C-1), (C-2), (D-1) and (D-2) are those in which R1 and R2 represent hydrogen atoms or alkyl, alkoxy, Hydroxy or cycloalkyl groups and R3, R4, R5, R6, R7 and for hydrogen atoms or Alkyl or cycloalkyl groups.

The compounds of formulas (C) and (D) include those from "Journal of The Chemical Society of Japan ", Part C, 1968 (14), pp. 1937 ff.," Journal of The Society of Synthetic Organic Chemistry ", Japan, 1970, 28 (1), pages 60 - 65, and "Tetrahedron Letters", 1973 (29), pages 2707-2710, known compounds and connections that can be produced by the methods described above.

Based on the magenta coupler (s) which can be used according to the invention the amount of the compounds of the formulas (C) and (D) is expediently 5 - 300, preferably 10-200 mol%.

Typical examples of compounds of the formulas (C) and (D) are: Connect- R 'R2 R3 R4 application no. C-11 11 ii 11 II CII. CIJ. C-12 11 11 II tl for (pro) C4g II II II iyi [Elonden- II <sation) Connect- R1 R2 R. fl Rs R6 ß7 ßs Idung R1 fr. I Ii 1 Il 11 ii II 11 CZ 1! II H Ii II II Cll3 CH3 Cs ii ii CII. 11 1 II Cll 3 Cll 3 C-4 CII. II CII. Cli. 11 II Cll3 CH3 I 011 II 11 ii II H ii C21i5 CH 3 C6 OCH. n HH II II II II C-7 OC3117 11 H II et al. 11 II C-8 OCi2IJ2s HH 11 HH II H C-9 Cll3COO II Ii n H 11 Cli. CII. C-10 CII. CONH H ff II - IJ B zu (Spiro) C-14 (Cll3) 2CCHCH2 (Cll3) 2CC} I2CR2 HH ii Ii CH3 C113 1 1 C-15 CII. CH3 HH II II CII. Cll3 C-16 (ClJ.) 2C = CJiCIJ2 (Cfl.) 2C = CCII2 H II II 11 CI13 CII. C-17 CQ H fl H fl HD II Connect- R1 R2 R3 R4 R5 R6 application no. D-1 CH3 CH3 HHHH D-2 HHHH CH3 CH3 Connect- R, R2 ß. R4 R5 R6 ß1 ßß application no D-3 II II Ii II H li II II D-4 11 11 HHHH CII. Cll3 D-5 CII. CII. II H II H CH3 CH3 D-6 (Cll.) 2CCll2Cll2 (CH3) 2CCH2CXI2 11 II 11 II CII. CH3 CQ D-7 II II C ca CQ ca II H D-8 II IX II II IJ Ii SPirO) CII.O Cll3n II Ii II H D-10 11 11 II II H CII CllOll Cll3 D-11 II II II H II II CII. CH3

Formula (E): In formula (E), R1 denotes a hydrogen atom or an alkyl, alkenyl, aryl, acyl or cycloalkyl group or a heterocyclic group; R³ is a hydrogen or halogen atom or an alkyl, alkenyl.

Aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxycarbonyl group and R2 and R4, which can be the same or different, in each case a hydrogen or halogen atom or an alkyl, alkenyl, aryl, acyl, Acylamino, sulfonamido-1 cycloalkyl or alkoxycarbonyl group.

The groups mentioned can be substituted by the other groups in each case be. Examples of such substituents are alkyl, alkenyl, alkoxy, aryl, Aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, carbamoyl, sulfonamido or sulfamoyl groups.

R1 and R2 together can complete a 5- or 6-membered ring. In this case, R³ and R4 stand for hydrogen or halogen atoms or alkyl, Alkenyl, alkoxy, alkenyloxy, hydroxy, aryl, aryloxy, acyl, acyloxy, sulfonamido or alkoxycarbonyl groups.

Y stands for a group of atoms that are used to form a chroman or coumaran ring is required.

The chroman or coumaran ring in question can be halogen, alkyl, cycloalkyl, alkoxy, alkenyl, alkenyloxy, hydroxy, aryl or aryloxy-substituted or substituted by a heterocyclic group and optionally form a spiro ring. Preferred compounds of the formula (E. ) are those of the formulas: In the formulas (E-1) to (E-5) the radicals R1, R2, R3 and R4 have the meaning of the corresponding radicals in formula (E). R5, R6, R7, R8, R9 and R10, which can be identical or different, stand for hydrogen or halogen atoms or alkyl, alkoxy, hydroxy, alkenyl, alkenyloxy, aryl or aryloxy groups or heterocyclic groups. Furthermore, R5 and R6, R6 and R7, R7 and R8, R8 and R9 or R9 and R10 together can complete a carbon ring. This can be substituted by an alkyl group.

Particularly suitable compounds of the formulas (E-1) to (E-5) are those in which R1, R2, R3, R4 and R5, which can be the same or different, represent hydrogen atoms or alkyl or cycloalkyl groups.

Preferred compounds of the formula (E-5) are those in where R3 and R4, which can be the same or different, each represent hydrogen atoms or alkyl, alkoxy, hydroxy or cycloalkyl groups. In both cases (formulas E-1 to E-5) represent R5, R6, R7, R8, R9 and R10, which may be the same or different may represent hydrogen atoms or alkyl or cycloalkyl groups.

The compounds of the formula (E) include those according to "Tetrahedron Letters", 1965, (8), pages 457-460, "Journal of The Chemical Society of Japan", Part C, 1966 (22), pages 2013 - 2016, and "Zh. Org. Khim.", 1870 (6), pages 1230 - 1237, compounds described and prepared by the methods described supra Links.

Based on the magenta coupler (s) which can be used according to the invention the amount of compounds of the formula (E) is expediently 5-300, preferably 10-200 mole percent.

Typical examples of compounds of the formula (E) are given below: 1Vrbin- Rs R2 ~ R. R4 Rs R6 Rz Rs fl3 no. 19 ii Ii II ii II il | Xondensation) E-2O C31 (7 ii II II II ii ') II fiondensation) E-21 II II 11 II 11 II F ii 1 (Spiro) II-L2 CM13 II II II Ii II $ jj 2 F-23 1l II II Ii II II C113 CB3 E-24 CII. II II II II CII. CII. E-25 CO II II II II II CI13 Cll 3 E-2O C121125 II II 11 CII. Cii. CII. C1120 Connect- R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 application no. E-1 HHHHHHHHHH E-2 HHHHHHHH CH3 CH3 E-3 HHHH CH3 HHH CH3 CH3 E-4 HH CH2 = CHCH2 HHHHH CH3 CH3 E-5 CH3 HHHHHHH CH3 CH3 E-6 C3H7 HHHHHHH CH3 CH3 E-7 C12H25 HHH CH3 HHH CH3 CH3 E-8 # -CH2 HHHHHHHHH E-9 # HHHHHHH CH3 CH3 E-10 # HHHHHHH CH3 CH3 E-11 HHHHHHHH CH3 C16H33 E-12 HH # HHHHH CH3 CH3 E-13 CH3 H CH3CO HHHHH CH3 CH3 E-14 CH3 HHHH Br Br HHH E-15 CH3 HHHH CQ CQ HHH E-16 CH3 HHHH CH3O Dr HHH E-17 CH3 HHHH OH Br H CH3 CH3 E-18 CH3 HHHH C2H5O OH H CH3 CH3 Verb in- dung Nur.'Ii R2 R3 R4 ßS R6 ru Rlo E - L7 11 11 Ii Ii ii 1 D 11 Ch Clis 11 11 ii ii 11 II ii 02N is <rCO ii ii Ii li ii ii ii 02 E-30 11 ii CI13 Ii Ii I (Cii. Clls E-31 C.111 11 ll II ll il II II 1-32 C3117 II ii 1 £ CII. Cl13 ii iI E- 37 11 Ii li Cll 3COt4JI Ii il ii Ii 1. - ii Ii ii 11 ii 11 li ii Connect- R1 R2 R3 R4 R5 R6 R7 R8 application no. E-33 HHHHHHHH E-34 HHHH CH3 CH3 HH E-35 C12H25 HHH CH3 CH3 HH E-36 CH3 H CH3 H CH3 CH3 HH Connection R3 R4 R5 R6 R7 R8 R9 R0 application no. E-39 HHHHHHHH E-40 HHHHHH CH3 CH3 E-41 OH HHHHH CH3 CH3 E-42 C3H2O H CH3 CH3 HHHH Formula (F): In formula (F), R1 denotes a hydrogen atom or an alkyl, alkenyl, aryl, acyl or cycloalkyl group or a heterocyclic group; R2 is a hydrogen or halogen atom or an alkyl, alkenyl, aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxycarbonyl group; R3 is a hydrogen or halogen atom or an alkyl, alkenyl, aryl, acyl, acylamino, sulfonamido, cycloalkyl or alkoxycarbonyl group and R4 is a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, alkenyloxy -, hydroxy, aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido or alkoxycarbonyl group.

The groups mentioned can be substituted by the other groups in each case be. Examples of such substituents are alkyl, alkenyl, alkoxy, aryl, Aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, carbamoyl, sulfonamido or sulfamoyl groups.

R1 and R² can together complete a 5- or 6-membered ring. In this case, R3 and R4, which may be the same or different, stand respectively for a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, alkenyloxy, Hydroxy, aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido or alkoxycarbonyl group.

Y represents one necessary to form a chroman or coumaran ring Atomic group.

The chroman or coumaran rings in question can be replaced by halogen atoms or alkyl, cycloalkyl, Alko: y, alkenyl, alkenyloxy, hydroxy, aryl or aryloxy groups or heterocyclic groups and optionally a spiro ring form.

Preferred examples of compounds of the formula (F) are those of the formulas: In the formulas (F-1) to (F-5) the radicals R1, R2, R3 and R4 have the meaning of the corresponding radicals in formula (F). R5, R6, R7, R8, R9 and R10, which can be identical or different, stand for hydrogen or halogen atoms or alkyl, alkoxy, hydroxy, alkenyl, alkenyloxy, aryl or aryloxy groups or heterocyclic groups.

R5 and R6 R6 and R7 R7 and R8, R8 and R9 or R9 and R10 can be used together form a carbon ring. This can be alkyl-substituted.

As already mentioned, in the formulas (F-3), (F-4) and (F-5) in each case two radicals R¹ to R10 are identical or different.

Of the compounds of the formulas (F-1) to (F-5), there are preferred, in which R1, R2 and R3 are hydrogen atoms or alkyl or cycloalkyl groups, R stands for a hydrogen atom or an alkyl, alkoxy, hydroxy or cycloalkyl group and R5, R6, R7, R8, R9 and R10 for hydrogen atoms or alkyl or cycloalkyl groups stand.

The compounds of formula (F) include those from "Tetrahedron Letters", 1970, Vol. 26, pp. 4743-4751, "Journal of The Chemical Society of Japan", 1972, No. 10, pp. 1987-1990, "Synthesis", 1975, Volume 6, pp. 392-393 and "Bul. Soc. Chem. Belg. ", 1975, Volume 84 (7), pp. 747-759, known compounds and according to the loc. Cit described method can be produced connections.

Based on the magenta coupler (s) which can be used according to the invention the amount of compound (s) of the formula (F) is expediently 5-300, more preferably 10-200 mole percent.

Typical examples of compounds of the formula (F) are given below: dun = 7 No. Rc R2 R. R4 Rs dun no. -11 nn (Condensation) F-12 C3117 11 1! II n II to II (Condensation) F-13 11 II II II II Ii ii ii F-14 II ii II ii ii Ii Cii. left F-15 ii U CII. II II II Cl13 11 F-16 II 11 i H Ii R CII. H F-17 11 II O II 11 11 Cii. 11th F-18 CzZ17 11 Cii. ii 1l 1l Cil 3 Ii F-19 O 11 g (Spiro) Ii li KM F-24 CtI2 = CPC112 Cit 3 Cl13 II n C21150 Cii. Cii. F-25 C3117 ii ii Il 11 o Cii. Cii. F-26 II C113 CH3 11 II Lai (Spiro) Connect- R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 application no. F-1 HHHHHHHHHH F-2 HHHH CH3 CH3 HH CH3 H F-3 HHHH CH3 CH3 HHHH F-4 H (CH3) 2C = CCHCH2 HH CH3 CH3 HHHH F-5 CH3 HHH CH3 CH3 HHHH F-6 C3H7 HHH CH3 CH3 HHH F-7 C12H25 HHH CH3 CH3 HHHH F-8 # -CH2 HHH CH3 CH3 HHHH F-9 # HHH CH3 CH3 HHHH F-10 # HHH CH3 CH3 HHHH F-20 H CQ HHH # (condenser- HHH sation) F-21 HHHH CH3 HH CH3 CH3 F-22 C3H7 (@) C @ H17 HH C2H5 HHHH F-23 CH3CO HHH CH3 HH CH3 H S. Connection j R R2 R1 R4 fls fl9 R10 1: -27 Ii II ii ii ii ii Cli. C113 F-28 C3117 ii 7 11 II II II ii C113 Cli. 1; -29 ii ii ii (t) c8117 ii Ii ii i 130 11 CQ 11 II II ii C 9 (game) ~ 2 1l II ii II ii Ci13 Cii. Connecting Application No. Rx R2 R3 R4 R7 R. Rs Rio v F-32 ii ii ii ii 11 11 Cii. Cli. F-33 Cli. 11 ii ii ii ii Cii. Cii. F-34 li Cii. 11 ii ii ii Ii ii F-35 Ii II H (t) C4119 li Ii CU3 C113 F86 íl CIi 11 II U II Clir CH3 F-37 U CB II Cll.SO2Nll II ii B II F-38 | 1U1 D ii ii II 11 CD, Cli. F-39 C121125 11 II II II Ii CII. CII. F-40 OCO Ii Ii H Ii ii (23 (Spiro) n II U to II Ii II CHs CII. v Application No. R3 R4 R5 R6 R7 R8 R9 R10 F-42 ii ii C! 13 Cli. 11 li ii ii F - 43. II U j3 (Spiro) Ii II ii F-44 ii 011 Cii. Cii. 11 ii Cii. II F-45 ii C31170 II ii ii 1 (Cii. ClJ2Oii F-46 011 ii Cii3 Cii. ii ii ii B F-47 C31170 il Cn3 Cii. ii ii ii ii

Formula (G): In formula (G), R¹ and R³, which can be the same or different, denote hydrogen or halogen atoms or alkyl, alkenyl, alkoxy, hydroxy, aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido -, cycloalkyl or alkoxycarbonyl groups and R2 is a hydrogen or halogen atom or an alkyl, alkenyl, hydroxy, aryl, acyl, acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxycarbonyl group.

The groups mentioned can be substituted by the other groups in each case be. Examples of such substituents are alkyl, alkenyl, alkoxy, aryl, Aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, carbamoyl, sulfonamido or sulfamoyl groups.

R² and R² together can form a 5- or 6-membered hydrocarbon ring to complete. This can be halogen, alkyl, cycloalkyl, alkoxy, alkenyl, hydroxyaryl or aryloxy substituted or substituted by a heterocyclic group be.

Y represents a group necessary to form an indane ring of atoms. The indane ring can be halogen, alkyl, alkenyl, alkoxy, cycloalkyl, hydroxy-, aryl- or aryloxy-substituted or substituted by a heterocyclic group and possibly a spiral ring form.

Of the compounds of formula (G), those of the formulas: preferred.

In the formulas (G-1) to (G-3), the radicals R1, R2 and R3 have the Meaning of the corresponding radicals in formula (G). R4, R5, R6, R7, R8 and R9, the can be the same or different, stand for hydrogen or halogen atoms or alkyl, alkoxy, alkenyl, hydroxy, aryl or aryloxy groups or heterocyclic groups Groups.

R4 and R5, R5 and R6, R6 and R7, R7 and R8 or R8 and R9 can be used together complete a hydrocarbon ring. This can be alkyl-substituted.

Of the compounds of the formulas (G-1) to (G-3), those preferred, in which R1 and R3 represent hydrogen atoms or alkyl, alkoxy, hydroxy or cycloalkyl groups, R2 for a hydrogen atom or an alkyl, hydroxy or Cycloalkyl group and R4, R5, R6, R7, R8 and R9 for hydrogen atoms or alkyl or cycloalkyl groups.

Based on the magenta coupler (s) which can be used according to the invention the amount of compound (s) of the formula (G) is expediently 5-300, more preferably 10-200 mole percent.

Typical examples of compounds of the formula (G) are given below: Connection R3 R3 R4 R5 R6 R R8 dun nu ru R2 R3 R4 R5 R5 No. G-1 ii II ii ii li ii Ii 1! Ii G-2 II n 11 1l 11 11 II Cii. CIls ii ii 11 ii H ii Ii U Ii Cii. Cm 61133 G-4 ii 011 II ii ii ii 11 CI13 C1 81133 ii ii 11 II 11 Cii. C112 II II Cii. Cii. G-6 11 CQ 11 Cii. C113 Ii ii C113 CII. (; -7 ca ca Cii. Cii. N II CII. Cll 3 C-8 ii ii Cii. Cii. CII. II 1I Cii. Cli. C-9 ii ll 11 ii II IItKonaenIf ii zI Ii G-10 H 11 II II 11 11 II If 7 (Spiro) C-11 ii C.ii, 'H Cli. Cl13 II H C. Cli. G-12 U (t) C.111 711 Cll3 CII. ii 11 - Cll3 Cii. l Cii B n H Cli. Clt 3 ii ii Cii. 3 II II il 11 O Cii. 11 li Clls Cii. (; -15 B II CIT30 Cii. Cli. Ii 11 Cii. Cii. G-16 Cll311 ii ii ii (3 (condens- ii Ii II 5 \ / sation) C -17 ii Cl13SO2NXI II CH 3 Cli. Ii ii Cii. Cli. G-18 ii Cl13CO ii CII. Cii. ii ii Cii. CIls C-l9 Ii ii Cii. CII. 11 ii Cii. Cii. G-20 11 (3Ci l CII. Cii. Ii II CII. Cl13 G-21 11 i onden-ll 11 li 1l ll ll ll C1! 3 ~ - sation) C -22 ii C113LAR1 Cii. Cii. ii 3 11 II Cii. Cl13 G-23 11 en-clay- Cii. C113 ii ii Cii. Cli. C -24 Cii. Cllif (Kon-. Cll a CIls Ii ii Cii. Cii. the- ii. Compound- R¹ R² R³ R6 R7 R8 R9 application no. G-29 HHHHH CH3 CH3 G-32 CH3 HHHH CH3 CH3 Connection Rl R, R3 R4 Rs R6 R7 manure No. G-25 11 Cl13 11 C113 C611s 11 11 C-26 ca ca Cl13 Cl13 ii II G-27 11 011 11 C113 CII. ii ii C-Z8 II C.1I? 11 Clfs Cli. n II C-30 II Cm 11 Cll. CII. a 11 II C-31 II C2115 II Cll3 Cii. il 11 E-33 Cii. Cli. H CII. Cii. II II G-34 U g H CII. CII. H ii (; -35 ii Cli. 11 11 ii ii II C-36 11 li ii 03 (Spiro) ii Cii. C113 ii ii Cii. Cl13 B II & -38 ii cii. U CII. C6ii5 fl ii C-39 3 ii ii Cii. Cii. 11 ii C-40 Cl13 Cii. 11 C21s C2ii5 II 11 G -41 ii ii ii ii 11 Cii. Cii. C-42 Ii 011 ii 03 (Spiro) II Ii G-43 11 OC112- 11 ii H II ii C-44 11 (t) C4lls 1I Cii. Cli. 11 ii G-45 ii (t) C811.7 1I C113 Cii. ii ii Formula (H): In formula (H), R1 and R2, which may be the same or different, denote hydrogen or halogen atoms or alkyl, alkenyl, aryl, acyl, acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxycarbony groups and R³ a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, hydroxy, aryl, aryloxy, acyl, acylamino, acyloxy, sulfonamido, cycloalkyl or alkoxydcarbonyl group.

The groups mentioned can be substituted by the other groups in each case be. Examples of such substituents are alkyl, alkenyl, alkoxy, aryl, Aryloxy, hydroxy, alkoxycarbonyl, aryloxycarbonyl, acylamino, carbamoyl, sulfonamido or sulfamoyl groups.

R1 and R2 or R2 and R3 together can have a 5- or 6-membered structure Complete the hydrocarbon ring.

This can be halogen, alkyl, cycloalkyl, alkoxy, alkenyl, hydroxy, aryl or aryloxy substituted or substituted by a heterocyclic group be.

Y stands for one required to complete an indane ring Group of atoms. The indane ring can be replaced by at least one previously for the hydrocarbon ring be substituted and optionally form a spiro ring.

Of the compounds of formula (H), those of the formulas: preferred.

In the formulas (H-1) to (H-3), the radicals R¹, R² and R3 have the Meaning of the corresponding radicals in formula (H). R4, R5, R6, R7, R8 and R9 stand for hydrogen or halogen atom or alkyl, alkoxy, hydroxy, alkenyl, aryl or aryloxy groups or heterocyclic groups.

R4 and R5, R5 and R6, R6 and R7, R7 and R8 or R8 and R9 can be used together complete an optionally alkyl-substituted hydrocarbon ring.

Preferred compounds of the formulas (H-1) to (H-3) are those where R¹ and R² represent hydrogen atoms or alkyl or cycloalkyl groups, R³ represents a hydrogen atom or an alkyl, alkoxy, hydroxy or cycloalkyl group and R4, R5, R6, R7, R8 and R9 represent hydrogen atoms or alkyl or cycloalkyl groups stand.

Processes for the preparation of compounds of the formula (H) are known. The compounds in question can, for example, according to the US Pat 3,057,939, "Chem. Ber.", 1972, 95 (5), pp. 1673-1674, and "Chemistry Letters", 1980, P. 739-742, known processes.

Based on the magenta coupler (s) which can be used according to the invention the amount of compound (s) of the formula (H) is expediently 5-300, more preferably 10-200 mole percent.

Typical examples of compounds of the formula (H) are given below: Compound- R¹ R² R³ R4 R5 R6 R7 R8 R9 manure No. H-1 HHHHHHHHH 2 CH3 HHHHHHHH 3 HHHHHHH CH3 C15H33 4 HH OH HHHHHH 5 CH2 = CHCH2 HC # HHHHHH 6 HHHHHHH CH3 CH3 7 HHH CH3 CH3 HHHH 8 HHH CH3 CH3 CH3 HHH 9 CH2 = CHCH2 H CH3O HHHHHH 10 HHH CH3 CH3 HH CH3 CH3 11 H C3H2 H CH3 CH2 HH CH3 CH3 12 C # HC # HHHH CH3 CH2 r EVerbin- application no. Rz Rz RE R4 Rs R6 R7 R8 ii -13 ii ii ii ii II onden- sation) 14 ii ii ii ii ii ii ii 71 (Spiro) i5 ii 3 in Cii. Cii. 11 ii CII. Cl13 16 ii CB3S02NII ii Cii. Cii. ll ii CIIs CU3 17 lI C113CO li ii 1l Ii Ii C1i3 C113 18 Ii I 'ii Cii. Cit 3 ii 1l CHa Cii. 19 ii Cll2ll U Cii. Cii. Ii ii CB 3 CIIJ 21 II onden-Cll. ii ii ii 1I Cll3 C113 sation) 22 H ll 11 Cii. II 11 Cli. Cii. r Connection Rt R1 R2 R. R6 R7 R5 Ro H-23 HHHHHHH 24 II H GH H II II II 25 CH3 II CH3 II II HH 26 HH CH3 HHHH 27 C CQ H CQ HH CII CH3 28 II II H II fl (3 (Spiro) 29 11 HH II H CH Cii 30 II H [DIn II II II HM 31 HH OCH2 II II CH3 CH3 36 H II (t) C4H9 HH CH3 CH3 Connection No. R1 R2 R3 R4 R5 R6 R7 H-32 HHHHHHH 33 HHH CH3 CH3 HH 34 HH (t) C4H9 CH3 CH3 HH 35 HH (t) C @ H17 CH3 CH3 HH Others: H-20 Formula (J): In the formula (J), R1 stands for an aliphatic group, a cycloalkyl group or an aryl group. Y represents a group of non-metallic atoms which - together with the nitrogen atom to which they are attached - are required to complete a 5-, 6- or 7-membered heterocyclic ring. The rule here is that in the event that the nitrogen-containing heterocyclic ring which is free of metal atoms contains two or more heteroatoms, not two heteroatoms are adjacent to one another.

Aliphatic groups which can be represented by R1 are, for example, optionally substituted alkyl or alkenyl groups, such as methyl, ethyl, butyl, octyl, dodecyl, Tetradecyl or hexadecyl or ethenyl or propenyl groups.

Cycloalkyl groups which can be represented by R1 are 5-, 6- or 7-membered Cycloalkyl groups such as cyclopentyl or cyclohexyl groups.

Aryl groups which can be represented by R1 are, for example, optionally substituted phenyl or naphthyl groups.

Examples of substituents of the aliphatic which can be represented by R1 Groups or cycloalkyl or aryl groups are alkyl, aryl, alkoxy, carbonyl, Carbamoyl, acylamino, sulfamoyl, sulfonamido, carbonyloxy, alkylsulfonyl, Arylsulfonyl, hydroxy, alkylthio or aryl thio groups or heterocyclic groups. Each of these substituents can in turn be substituted be.

In formula (J), as already mentioned, J stands for that group non-metallic atoms that (together with the nitrogen atom) to complete a 5-, 6- or 7-membered heterocyclic ring are required. But when here heterocyclic rings with several heteroatoms are no longer allowed be arranged adjacent to one another as two heteroatoms. It is therefore inexpedient that in the hetero rings of compounds of the formula (J) all heteroatoms are one another are adjacent, since the connection in question is no longer effective in this case as an image stabilizer for the magenta dye image.

The 5-, @- or 7-membered heterocyclic rings of the compounds of the formula (J) can be substituted by substituents such as alkyl, aryl, acyl, carbamoyl, Alkoxycarbonyl, sulfonyl or sulfamoyl groups, which in turn are also substituted can be substituted. The 5-, 6- or 7-membered heterocyclic rings are expediently saturated. A benzene ring can be attached to the heterocyclic ring and the like. Be condensed.

Furthermore, a spiroring system can be formed.

Based on the magenta coupler (s) which can be used according to the invention the amount of the compound (s) of the formula (J) is appropriately 5-300, preferably 10-200 mole percent.

Typical examples of compounds of the formula (J) are given below: Connect R² R³ R4 R5 R6 R7 R8 R9 R10 R11 No. J-1 C12H25 C12H25 HHHHHHHH J-2 C14H29 C14H29 HHHHHHHH J-3 C14H29 HHHHHHHHH J-4 C14H29 CH3CO HHHHHHHH J-5 C16H33 C16H33 HHHHHHHH J-6 C14H29 CH3 HHHHHHHH J-7 # -CH2 # -CH2 HHHHHHHH J-8 # # HHHHHHHH J-11 CH3 # HHHHHHHH J-13 C14H29 C1H3NHCO HHHHHHHH J-14 (t) C8H17 3-CH2 HHHHHHHH J-15 C14H29 CF3CO HHHHHHHH J-16 C14H29 C2H5OCO HHHHHHHH J-17 CH3 # HHHHHHHH J-18 C14H29 C14H29 CH3 HHHHHHH J-19 C14H29 C14H29 CH3 HHHHH CH3 H J-20 C14H29 C14H29 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 J-21 CH3 # HHHHHHHH J-22 C12H25 CH3 CH3 HHH CH3 HHH J-23 C12H25 C12H25 CH3 HHHHH CH3 H J-24 C16H33 C16H33 CH3 HHHHH CH3 H J-25 C6H5CH = CH-CH2-C12H25 HHHHHHHH J-26 C12H25 C2H5 CH3 HHHHHHH J-27 C16H33 H C2H5 HHHHHHH J-29 C14H29 CH2BrCH2 HHHHHHHH J-30 CH3O (CH2) 4 CH3O (CH2) 4 HHHHHHHH = R 2 R3 R4 J-9 C14ii29 (Cii2) 2 Cl 4H2s J -10 (t) Csils7 (cit2) 6 (t) C.iiL? J-12 Cd 41129 Cii2 Cm 41129 J-Z8 Cs 2H25 C112 C112 Cl 2112s J-Z8 C12ll26 Cj21125 X R1 J-31 0 C12H25 J-32 0 C14112s J-33 0 CsHsCll = Cll J-34 0 Cll COHH J-350 ot-naphthyl J-36 0 OCHCONH e (CH2) 3 ~ C15H.1 C2ll J-37 0 HO - so -a, CHCONH --- (CHt) J- J-38 0 O S02NHCH2- sll11 (t) J -39 O t-CsHs} <CHC3NH- (C82) 2- 12th C2Hs J-40 0 L / N-Cu2Cll2 J-41 S C141129 Csll1: J-42 S t-C5ll1 1OC, ll2C0NII CH2- C2lls J-43 SO S02NHCll2- J-44 S J -45 S / -7-CH7- R1 R2 J-46 Cg2H2s C12112s J-47 C141129 C14H29 J-48 C6HsCH2 C6HsCH2 J-49 C16H .. H J-50 C16H .. CH3CO R'-N N-R2 LW J-51 C, 6H33 C16H33 J-52 C4H2s C141129 J-53 Cj2H2s C12H25 J-54 Cl4H2s CH3CO J-55 Cs4H2s CF3CO J-56 C2Hs (t) C5H (t) CsHit¼ / \ Csc? Cilll (fC) o J-57 Cd 41129 C2H5OCO J-58 C141129 CH3NHCO J-59 C141129 CHsS02 J-60 C14II29 (CH3) 2NS02 J-61 C12H25 Cl2Hzs-N N -CH2- CsHal (t) J-62 II (t) CslliiOC1llCOHH (Cll2): C2lls Particularly suitable examples of compounds of the formula (J) are the piperazine and homopiperazine compounds. Preferred compounds of the formula (J) are those of the formulas: In the formulas (J-1) and (J-2), R2 and R3 stand for hydrogen atoms or alkyl or aryl groups, with the proviso that R2 and R3 do not simultaneously stand for hydrogen atoms. R4 to R13 represent hydrogen atoms or alkyl or aryl groups.

The alkyl groups represented by R2 and R3 are, for example Methyl, ethyl, butyl, octyl, dodecyl, tetradecyl, hexadexyl and octadecyl groups. An aryl group that can be represented by these radicals is, for example, the phenyl group. The alkyl and aryl groups can, for example, halogen, alkyl, aryl, alkoxy or aryl oxy-substituted or by heterocyclic groups be substituted.

The total number of carbon atoms of radicals R2 and R3 inclusive its substituents are preferably 6 to 40.

The alkyl groups represented by R4 to R13 are, for example Methyl or ethyl groups. An aryl group representable by R4 to R13 is, for example the phenyl group.

Typical examples of the piperazine compounds mentioned are Compounds (J-1) to (J-30), for the homopiperazine compounds mentioned, the compounds (J-51) to (J-62).

The following are two typical production examples for the present invention Usable magenta image stabilizers of the formula (J) indicated: Preparation example 1 (preparation of the compound (J-2)) 9 g of piperazine and 55 g of myristyl bromide dissolved in 100 ml of acetone, whereupon the resulting solution with 15 g of anhydrous potassium carbonate is moved. The resulting reaction mixture is refluxed for 10 hours to react heated. When the reaction has ended, the reaction mixture is poured into 500 ml of water. The whole is then extracted with 500 ml of ethyl acetate. After drying the obtained Ethyl acetate extract with magnesium sulfate, the ethyl acetate is distilled off. Here a white crystalline residue is obtained. When recrystallizing from 300 ml Acetone is obtained 34 g (70% yield) white flaky crystals an mp of 55-580C.

Production Example 2 (Production of Compound (J-34)) 18 g of 4-morpholine aniline are dissolved in 100 ml of ethyl acetate, whereupon the resulting solution is gradually taken Stir while maintaining the temperature of the reaction solution at 200C 12 ml of acetic anhydride are added. Thereafter, the reaction solution with Ice chilled. The crystals which have precipitated out are filtered off. In the end the filtered crystals are recrystallized from ethyl acetate, whereby 16.5 g (75% yield) of white powder-like crystals with a melting point of 207-210 ° C. were obtained will.

Formula (K): In the formula (K), R1 denotes an aliphatic group or a cycloalkyl or aryl group, Y simply a bond or a divalent hydrocarbon group which is necessary (together with the nitrogen) to complete a 5- to 7-membered heterocyclic ring, and R2 , R3, R4, R5, R6 and R7 are hydrogen atoms, aliphatic groups or cycloalkyl or aryl groups. The rule here is that R2 and R4 or R3 and R6 simply represent a bond with one another, so that together with the nitrogen atom and Y there is an unsaturated 5- to 7-membered heterocyclic ring. If Y simply stands for a bond, R5 and R7 can likewise simply represent a bond with one another, so that, together with the nitrogen atom and Y, an unsaturated 5-membered heterocyclic ring is formed. If Y does not simply represent a bond, R5 and Y, R7 and Y or Y itself can represent an unsaturated bond, so that, together with the nitrogen atom and Y, an unsaturated 6- or 7-membered heterocyclic ring is formed.

The aliphatic groups representable by R1 are, for example optionally substituted alkyl or alkenyl groups, such as methyl, ethyl, butyl, Octyl, dodecyl, tetradecyl or hexadecyl groups or ethenyl or propenyl groups.

The cycloalkyl groups represented by R1 are, for example, optional substituted 5- to 7-membered cycloalkyl groups, such as cyclopentyl or cyclohexyl groups.

The aryl groups representable by R1 are, for example, optional substituted phenyl or naphthyl groups.

Examples of aliphatic groups or cycloalkyl groups that can be represented by R1 or aryl groups are alkyl, aryl, alkoxy, carbonyl, carbamoyl, acylamino, Sulfamoyl, sulfonamido, carbonyloxy, alkylsulfonyl or hydroxy groups, heterocyclic Groups or alkylthio or arylthio groups. These substituents can in turn also be substituted.

As already mentioned, Y in formula (K) stands for a single bond or a divalent hydrocarbon group, which together with the nitrogen atom is required to form a 5- to 7-membered heterocyclic ring. if Y stands for a single bond, R5 and R7 together can represent a single bond, so that an unsaturated 5-membered heterocyclic ring is formed. If Y is for a divalent hydrocarbon group, e.g., a methylene group R5 and Y or R7 and Y represent an unsaturated bond, so that an unsaturated one 6-membered heterocyclic ring is formed. When Y stands for an ethylene group, R5 and Y, R7 and Y or Y itself can represent an unsaturated bond, so that an unsaturated 7-membered heterocyclic ring is formed. The ones represented by Y divalent hydrocarbon groups can be substituted. Suitable substituents are for example alkyl, carbamoyl, alkyloxycarbonyl, acylamino, sulfonamido, Sulfamoyl or aryl groups or heterocyclic groups.

In formula (K), R2, R3, R4, R5, R6 and R7 represent hydrogen atoms, aliphatic groups or cycloalkyl or aryl groups. Those that can be represented by R2 to R7 aliphatic groups are optionally substituted alkyl or alkenyl groups, such as methyl, ethyl, butyl, octyl, dodecyl, tetradecyl or hexadecyl groups or ethenyl or propenyl groups.

The cycloalkyl groups represented by R2 to R7 are, for example optionally substituted 5- to 7-membered cycloalkyl groups, such as cyclopentyl or cyclohexyl groups.

The aryl groups representable by R2 to R7 are, for example possibly substituted phenyl or naphthyl groups.

Examples of substituents on the aliphatic which can be represented by R2 to R7 Groups or cycloalkyl and aryl groups are alkyl, aryl, alkoxy, carbonyl, Carbamoyl, acylamino, sulfamoyl, sulfonamido, carbonyl, alkylsulfonyl, arylsulfonyl or hydroxy groups, heterocyclic groups, or alkylthio groups.

Of the compounds of the formula (K) those with 5- to 7-membered, saturated heterocyclic rings are preferred to those with unsaturated rings.

Based on the magenta coupler (s) which can be used according to the invention of the formula (I), the amount of compound (s) of the formula (K) is expediently 5 to 300, preferably 10 to 200 mol%.

Typical examples of compounds of the formula (K) are given below: Vr = ind Rl R2 R3 R4 R5 Y 1 II C8HI HHHH K 2 CH3CONH OHHHH II II II II 011 K3 CN 11 II HH K-4 C121125 II HHH K-5 C1 41129 HHHH K 6 C 6H33 HHHH K-6 C16H33 HHHH 7- (CH 2) 1 K-7 Cs 4H29 H 11 Hzs -N 112 II K 8 CH, CH3 CH3 HH K-9 CsllsCH = CHCli: HHHH C51111 (t) K-10 (t) C5H1 (t) C5HIOCH2CONBCH II II HH R RZ RZ R4 RS R6 K-11 (t) C.ii17 Ii ii D II ii K-12 Cll3CONIX 11 11 il H If K-13 Erz1125 ii II ii ii li K-14 Cr, 1I ii 11 n II II K-15 C, 61133 Ii Ii If II H. K-16 C, 41129 CII. ii ii ii ii K-17 (t) C5ii1 45OI {C (OhO (CII2) 2 " C4119 K-18 C8ii17 Cii. CII. Cii. ii Cii. Cii. K-19 Il (Cll2) s Cii. ii n Cll3 ii CII. K-20 Cii. 11 ii 2112sOCOCI12 ~ li ii K-21 Cii. Clla ii C16I1330COC112- ii Cll3 K-22 Cii. C15i13. ii il ii ii K-23 C6115 ii ii C, 2112sOCO ~ II U K-24 Cii. C6115 1l ii 1l ii K-25 ii ii ii ii Ii R1 R2 K-26 C. 1117 II 3 ~~ II K-23 fÄ \ CH- II R R2 IK 26 C8H 7 H 1 K 2 {CN3CUNH OH IK 28 CNcazOCH2- H K-29 C141129 II N - (CH2) 8 - H K-31 C16H7 CH3 K - 32 d K-33 / C5Hii (t) H (t) CsHi 1 -OCHC0NHCH2- C4ll

The following is a typical compound preparation example of the formula (K) indicated: Preparation example 3 (preparation of the compound K-14) 9 g of piperazine and 28 g of myristyl bromide are dissolved in 60 ml of acetone whereupon the obtained 6.0 g of anhydrous potassium carbonate are added to the solution. The reaction mixture obtained is heated to reflux temperature for 20 hours for reaction. After completion of the implementation the reaction mixture is poured into 300 ml of water. After extraction with 300 ml The ethyl acetate obtained is dried with magnesium sulfate and then ethyl acetate freed from ethyl acetate by distillation. This gives a white crystalline Precipitation. Recrystallization from 100 ml of acetone gives 12 g (43% yield) white flaky crystals with a m.p. 175-1800C.

The hydrophilic colloid layers, e.g. protective layers, intermediate layers and the like of color photographic recording materials according to the invention for copying purposes may contain U7 absorbents. These are used to reduce static electricity fogging caused by rubbing the recording materials and by Effect of UV radiation on the light-sensitive recording materials to avoid resulting image impairment.

Recording materials according to the invention can contain additional layers, such as filter, antihalation and / or exposure preventing layers. These layers and / or the emulsion layers can also contain dyes, which when developing from the drawing materials leak or bleached.

To reduce the gloss, to improve the touchability and to avoid adhesion of several photosensitive recording materials to each other) can in the silver halide emulsion layers and / or other hydrophilic Colloid layers of recording materials according to the invention, roughening agent ' be included.

Furthermore, the recording materials according to the invention can be used for Contain lubricants to reduce sliding friction.

To prevent static charging, the recording materials according to the invention antistatic agents are incorporated. Such antistatic Agents are sometimes in their own, on the emulsion-free side of the support provided antistatic layer. On the other hand, the antistatic Means also in a protective layer next to the emulsion layer and / or on the emulsion-coated Layer carrier side can be accommodated. Furthermore, in the photographic emulsion layers and / or other hydrophilic colloid layers of recording materials according to the invention wetting agent be housed. These serve to improve the coating behavior improve, prevent static electricity, improve lubricity, to improve the emulsion / dispersion properties, to prevent adhesion and the photographic properties such as development acceleration, hardening and raise awareness, improve.

For color reproduction of an image in the frame of a Color subtraction process becomes the reflective support of a color photographic material suitable for copying purposes Recording material according to the invention in a suitable amount and suitable arrangement with silver halide emulsion layers containing magenta, yellow and cyan couplers and non-photosensitive layers. Depending on the intended use the amount and arrangement of the layers concerned may be appropriately changed will.

In the case of a recording material according to the invention, the upper side of the film carrier can be coated directly or via at least one adhesive layer. This adhesive layer (s) serves to improve the adhesive properties, antistatic properties, Dimensional stability, abrasion resistance, hardness, antihalation properties, friction properties and / or other properties.

If necessary, the substrate is topped before coating subjected to a corona discharge, irradiated with light or flamed.

In order to improve the application properties, the of a recording material according to the invention used emulsion (s) a thickener incorporated. For application, it is advisable to use an extrusion or curtain coating process, since this involves two or more layers at the same time can be applied.

In the case of recording materials according to the invention, the image reproduction can be achieved by any color development process.

In the intermediate color developer, common ones in photography are used known primary aromatic amine color winder connections for use. These are, for example, aminophenol and p-phenylenediamine derivatives. These compounds usually come in the form of their salts, e.g. their chlorides or sulfates, and not in free form, as the salts are more stable.

The amount of color developing agent is per liter of color developing bath about 0.1 to about 30, preferably about 1 to about 15 g.

Suitable aminophenol color developing agents are, for example o-aminophenol, p-aminophenol, 5-amino-2-oxytoluene, 2-amino-3-oxytoluene and 2-oxy-3-amino-1,4-dimethylbenzene.

Particularly useful primary aromatic amine color developing agents are N.N'-dialkyl-p-phenylenediamine compounds, the alkyl and phenyl groups of which are any Can carry substituents. Particularly suitable examples are N, N'-diethyl-p-phenylenediamine chloride, N-methyl-p-phenylenediamine chloride, N, N'-dimethylp-phenylenediamine chloride, 2-amino-5- (N-ethyl-N-dodecylamino) toluene, N-ethyl-N-ß-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate, N-ethyl-N-ß-hydroxyethylaminoaniline, 4-amino-3-methyl-N, N "-diethylaniline and 4-amino-N- (2-methoxyethyl) -N-ethyl-3-methylaniline ptoluenesulfonate.

When developing recording materials according to the invention can the developer baths in addition to the aforementioned primary aromatic amine developer compounds also a wide variety of customary additives to color developer baths, e.g. alkaline ones Compounds such as sodium hydroxide, sodium carbonate, potassium carbonate, alkali metal sulfites, Alkali metal bisulfites, alkali metal thiocyanates, alkali metal halides, benzyl alcohol, Water softening contain agents, thickeners and the like. Of the The pH of such color developing baths is normally not less than 7, preferably about 10 to about 13.

A light-sensitive color photographic material suitable for copying purposes Recording material according to the invention is color-developed (after exposure) and then fixed with the help of a suitable treatment bath.

If the treatment bath consists of a fixer bath, before fixing bleached. Metal complex salts of inorganic acids are suitable as bleaching agents. Such metal complex salts act to the effect that they are formed during development oxidize metallic silver and convert it back into the silver halide. Simultaneously the undeveloped color parts of a color developing agent are color-developed. Such metal complex salts consist of an aminopolycarboxylic acid or an organic one Acid, such as oxalic or citric acid, and thus coordinatively bound metal ions, like iron, cobalt or copper ions. Preferred for forming such metal complexes organic acids are polycarboxylic acids or aminocarboxylic acids. This polycarbonate or aminocarboxylic acids can be in the form of their alkali metal, ammonium or water-soluble Amine salts are used.

Typical examples of such acids are: (1) ethylenediaminetetraacetic acid, (2) nitrilotriacetic acid.

(3) iminodiacetic acid, (4) disodium ethylenediaminetetraacetate, (5) Tetra (tri) methylammonium ethylenediaminetetraacetate, (6) tetrasodium ethylenediaminetetraacetate and (7) sodium nitrilotriacetate.

The bleach baths to be used can in addition to the as Bleach The various metal complex salts of organic acids used are also used usual additives included. Appropriate additives are alkali metal halides or Ammonium halides, especially rehalogenating agents such as potassium bromide Natri'-trc; id, Sodium chloride and ammonium bromide, metal salts and chelating agents.

In addition, the bleach baths can contain the usual eknn-e pH buffers, such as borates, Oxalates, acetates, carbonates and phosphates, or else alkylamines, polyethylene oxide, contain.

Furthermore, the fixing baths and bleach / fixing baths can have one or several pH buffers, e.g. sulfites such as ammonium sulfite, potassium sulfite, ammonium bisulfite, Potassium bisulfite, sodium bisulfite, ammonium metabisulfite, potassium metabisulfite, sodium metabisulfite and the like, and a wide variety of salts, such as boric acid, borax, sodium hydroxide, potassium hydroxide, Sodium carbonate, potassium carbonate, sodium bisulfite, sodium bicarbonate, potassium bicarbonate, Acetic acid, sodium acetate and ammonium hydroxide.

That for treating a recording material according to the invention used bleach / fix bath can be replenished with a bleach / fix replenisher respectively.

can be added. Both the bleach / fix bath and the replenisher may contain a thiosulfate, thiocyanate, sulfite and the like.

For further activation, the bleach / fix bath or the bleach / fix replenisher solution can be oxygen or air blown. on the other hand a suitable oxidizing agent, e.g. Hydrogen peroxide, a bromate, a persulfate and the like.

be incorporated.

The following examples are intended to illustrate the invention in more detail.

EXAMPLE 1 In the presence of an inert gelatin, a polydisperse silver chlorobromide emulsion having a silver bromide content of 80 mol%, an average grain size (r) of 0.60 μm and a coefficient of variation (S / r) of 0 is produced as part of a normal precipitation process, ie a single jet precipitation process , 25 prepared. The resulting emulsion is treated with sodium thiosulphate and a spectral sensitizing dye of the formula: offset. The emulsion EM-1 obtained in this way serves as a green-sensitive emulsion. A magenta coupler is one of the formula: used. The solvent S-3 is used as the high-boiling organic solvent. The emulsion EM-1, the coupler M-1 and the high-boiling organic solvent S-3 are dispersed in an aqueous gelatin solution by means of a sonic dispersion device, whereupon the resulting dispersion is applied to a paper support laminated with polyethylene on both sides to form the third layer. The remaining layers, the composition of which is shown in Table 1 below, are then applied in such a way that a light-sensitive color photographic recording material (test specimen 1) suitable for copying purposes is obtained.

TABLE I 7th layer: Gelatin hardening agents of the formula: 6th layer: UV absorber of the formula: Gelatin 5th layer: red-sensitive silver chlorobromide emulsion having a silver bromide content of 60 mol%; Amount of silver applied: 0.25 g / m2 carrier area Blue-green coupler of the formula: Dioctyl phthalate gelatin continued TABLE I: 4th layer: UV absorber of the formula: 3rd layer: green sensitive emulsion (EM-1); amount of silver applied: 0.40 g / m 2 support area magenta coupler M-1 dioctyl phthalate gelatine 2nd layer: gelatine 1st layer: blue-sensitive silver chlorobromide emulsion with a silver bromide content of 90 mol%; Amount of silver applied: 0.35 g / m2 carrier area Yellow coupler of the formula: Dioctyl phthalate gelatin support In the presence of inert gelatin, a monodisperse silver chlorobromide emulsion having a silver bromide content of 80 mol%, an average grain size (r) of 0.53 μm and a coefficient of variation (S / r) of 0.13 is also prepared in a double jet precipitation process. Here, the flow is regulated at 50 ° C. in such a way that conditions exist in which no new grains are formed in the course of grain growth. Sodium thiosulfate and the sensitizing dye of the formula D-1 are added to the emulsion formed at 550 ° C., an emulsion EM-2 being obtained.

According to test item 1, test items 2 and 3 are produced, with however, in both cases the emulsion EM-2 is used and the respective amount of silver in the green-sensitive emulsion layer 0.35 g / m2 support surface or 0.32 g / m2 Support surface is.

Corresponding to emulsion EM-2, a further monodisperse silver chlorobromide emulsion is used a silver bromide content of 80 mol%, an average grain size (r) of 0.39 µm and a coefficient of variation (S / r) of 0.14, although the mixing temperature is 400C. The emulsion obtained is in a corresponding Manner as the emulsion EM-2 is chemically sensitized, whereby an emulsion EM-3 is obtained will.

In a manner similar to that of emulsion EM-2, another becomes monodisperse Silver chlorobromide emulsion having an average grain size (r) of 0.65 µm and a coefficient of variation (S / r) of 0.12, but with the mixing temperature 600C. The emulsion obtained is chemically sensitized in accordance with emulsion EM-2 and treated to obtain an emulsion EM-4.

According to test item 1, further test items 4 and 5 are produced, however, the emulsions EM-3 and EM-4 in the ratio of their adjusted to 1: 1 Silver contents mixed together and the mixture as a green-sensitive emulsion Applied in amounts of silver of 0.37 g / m2 support surface or 0.34 g / m2 support surface will.

A test item 6 is produced in the same way as the test item 1, however, using the magenta coupler (44) and the green sensitive emulsion is applied in such an amount that 0.20 g of silver is required per m2 of support surface.

A test item 7 is produced in the same way as the test item 2, however, using the magenta coupler (44) and the green sensitive emulsion is applied in such an amount that 0.17 g of silver is used per m2 of support surface.

A test item 8 is produced in the same way as the test item 4, however, using the magenta coupler (44) and the green sensitive emulsion is applied in such an amount that 0.19 g of silver is used per m2 of support surface.

From the test items 1 to 8, special attention is paid to the color balance the gradation properties are determined as follows: The test items 1 to 8 are determined by means of of a commercially available sensitometer through a step wedge and then in treated in the manner described below.

Care is taken that the exposure conditions each be adjusted so that the color density achieved after the treatment at a Density of about 1.0 is neutral.

Treatment steps: Color development: 380C 3 min 30 s bleaching and Fixing 330C 1 min 30 s soaking 25-350C 3 min drying 75-800C about 2 min Es The following treatment baths are used: Color developer bath benzyl alcohol 15 ml Ethylene glycol 15 ml potassium sulfite 2.0 g potassium bromide 0.7 g sodium chloride 0.2 g potassium carbonate 30.0 g hydroxylamine sulfate 3.0 g polyphosphoric acid 2.5 g 3-methyl-4-amino-N-ethyl-N- (B-methanesulfonamidoethyl) anilinesulfonate 5.5 g brightener (4,4'-diaminostilbene disulfonic acid derivative) 1.0 g potassium hydroxide 2.0 g made up to 1 l with water, the pH is adjusted to 10.20.

Bleach / fixer iron (III) ammonium ethylenediaminetetraacetate, dihydrate 60.0 g ethylenediaminetetraacetic acid 3.0 g ammonium thisoulfate (70% solution) 100 ml ammonium sulfite (40% solution) 27.5 ml the pH is with potassium carbonate or Glacial acetic acid adjusted to 7.1 made up to 1 1 with water.

The treated samples are checked for their neutrality at the density points rated at about 0.5, 1.0, 1.5 and 2.0, respectively. A standard color chip ( in accordance with Japanese Industry Standard Z8721 under supervision of The JIS Color Chip Committee of The Japan Standards Association). When evaluating of the gradation properties concerned becomes a test piece in each density range is neutral, rated as the best candidate. A test specimen with a more strongly shifted Density is rated as worse in terms of its gradation properties.

The results of this evaluation can be found in the following table II.

When evaluating the neutrality in the density points of about 0.5, 1.0, 1.5 and 2.0 mean N an approximately neutral representation, M, C, B and G one Shift in neutrality to purple, blue-green, blue or green.

TABLE II Test item no. Purple-green-sensitivity-applied- evaluation of neutrality coupler emulsions Sil- sion superset density density density density in the at at at at at at at at at at 3rd layer wa 0.5 wa 1.0 wa 1.5 wa 2.0 (g / m² carrier ger area) 1 (comparative test item) M-1 EM-1 0.40 NNNN 2 (")" EM-2 0.35 C # BNMM 3 (")""0.32 C # BNNG 4 (")" EM-3 + EM-4 0.37 NNNM 5 (")""0.34 NNGN 6 (") Purple EM-1 0.20 MNNG coupler 44 7 (inventive according to) "EM-2 0.17 NNNN 8 (")" EM-3 + EM-4 0.19 NNNN Table II shows that the test pieces according to the invention in which a monodisperse emulsion is combined with a magenta coupler of the formula (I) (test pieces 7 and 8) have excellent gradation properties.

To determine the other photographic properties Samples 1 to 8 for their sensitivity to pressure desensitization examined. The results obtained can be found in Table III.

Assessment of the sensitivity to pressure-induced desensitization.

A test specimen is exposed uniformly in such a way that the magenta color density after development is about 0.5. Then the test item is at 250C and one relative humidity of 25% around a stainless steel rod of one diameter bent around by 5 mm. The test specimen is then carried out in the manner described color developed and then measured for its purple density. The lower the The change in density, the lower the susceptibility to a pressure-induced Desensitization.

TABLE III DUT No. Sensitivity opposite pressure 1 (comparative -0.15 examinee) 2 "-0.01 3 "0.00 4 "-0.02 5 "-0.02 6 "-0.13 7 (according to the invention) -0.01 8 "-0.01 It can be seen from Table III that test pieces 1 and 6 experience a considerable desensitization on application of pressure, and that already on application of pressure, as occurs with normal rubbing. The remaining test specimens are practically not desensitized at a pressure that occurs with normal rubbing.

The one that is highly susceptible to desensitization when exposed to pressure Test specimen 1 shows good gradation properties, which is disadvantageous in this test specimen are however (besides its pressure sensitivity) its high, on the required manufacturing costs attributable to large quantities of silver.

The gradation properties of test items 2, 3, 4 and 5 always leave still left to be desired, although it is a magenta coupler which can be used in accordance with the invention contain.

Only through the combination of a monodisperse emulsion and one according to the invention usable magenta couplers of the formula (I) can be obtained in an inexpensive manner to a light-sensitive color photographic recording material suitable for copying purposes excellent gradation properties and low sensitivity to a pressure-induced desensitization.

Example 2 As in Example 1, using the emulsions EM-1 and EM-2 as green-sensitive emulsions, the magenta coupler according to the table IV and the solvent S-12 as a high-boiling organic solvent for the respective magenta couplers and in compliance with those given in Table IV Silver application quantities test specimens 9 to 21 produced.

The gradation properties of the specimens 9 to 21 are corresponding to Example 1 certainly. The results obtained can be found in the following table IV.

Furthermore, according to Example 1, their sensitivity to pressure-induced desensitization is determined for the test objects 9 to 21. The related results can also be found in Table IV. TABLE IV Assessment of neutrality sensitive Test item purple-red- green- applied speed against- No coupler sensitivity- amount of silver density density density density above one liche in the at et- at et- at et- at et- pressure industry Emulsion 3rd layer wa 0.5 wa 1.0 wa 1.5 wa 2.0 (g / m² carrier sensitivity area) ization 9 (Invention Purple-EM-2 0.16 NG NNN -0.03 according to coupler 5 10 (")" 18 "0.17 NG NNN -0.02 11 (")" 28 "0.17 NNNN -0.01 12 (")" 45 "0.18 NNNN -0.01 13 (")" 59 "0.16 NNNN -0.02 14 (")" 104 "0.19 NM NNN -0.03 15 (")" 127 "0.17 NNNN -0.03 16 (")" 152 "0.19 NNNN -0.04 TABLE IV: Test item purple-green- applied assessment of neutrality sensitive- No. Coupler sensitivity silver quantity density density density density against- liche in the one at one at one at one at one at one at another Emulsion 3rd layer wa 0.5 wa 1.0 wa 1.5 wa 2.0 pressure induction (g / m² backed de- area) sensitive ization 17 (comparative specimen) M-2 ¹ EM-2 0.18 GNMM -0.01 18 (")""0.16 CG NNG -0.02 19 (")" EM-1 0.19 NNNN -0.17 20 (") M-32 EM-2 0.35 MNGG 0.00 21 (")""0.38 MNNM -0.01 1: purple coupler: 2: purple coupler: From Table IV it can be seen that color photographic light-sensitive recording materials suitable for copying and having excellent gradation properties and other photographic properties can only be obtained inexpensively if a monodisperse emulsion is combined with a magenta coupler of the formula (I) in the green-sensitive layer.

Claims (13)

PATENT CLAIMS 1. Light-sensitive color photographic recording material for copying purposes with a reflective layer support on which at least one blue-sensitive, green-sensitive and red-sensitive silver halide emulsion layer is applied, characterized in that the silver halide emulsion of the green-sensitive silver halide emulsion layer is a monodispersed silver halide emulsion with this monodispersed silver halide emulsion a purple coupler of the formula: wherein: Z represents a group of non-metallic atoms required to form an optionally substituted nitrogen-containing heterocyclic ring; X is a substituent which can be split off upon reaction with an oxidation product of a color developing agent, and R is a hydrogen atom or a substituent. 2. Recording material according to claim 1, characterized in that the magenta coupler of the formula (I) is one of the formulas: worn R1 to R8 or X have the meaning of R or X in formula (I) contains. 3. Recording material according to claim 1, characterized in that the magenta coupler of the formula (I) is one of the formula: in which R1, X and Z1 have the meanings of R, X and Z in formula (I). 4. Recording material according to claim 1 or 2, characterized in that the radicals R and R1 of the formula: wherein R9 and R10, which can be the same or different, each represent a hydrogen atom or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or aryl group, a heterocyclic group, an acyl, sulfonyl, sulfinyl, phosphonyl -, carbamoyl, sulfamoyl or cyano group, a residual group of a spiro compound, a residual group of a bridging hydrocarbon, an alkoxy or aryloxy group, a heterocyclic oxy group, a siloxy, acyloxy, carbamoyloxy, amino, acylamino, sulfonamide, imide -, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, alkylthio or arylthio group or a heterocyclic thio group. 5. Recording material according to claim 4, characterized in that that both radicals R9 and R10 stand for alkyl groups. 6. Recording material according to claim 4, characterized in that that the radicals R9 and R10 together with the carbon atom to which they are attached, a Form cycloalkyl group. 7. Recording material according to claim 1, characterized in that that the amount of magenta coupler of the formula (I) is in the range from 1 x 10 3 to 8 x 10-1 moles per mole of the silver halide. 8. Recording material according to claim 2, characterized in that that the magenta coupler of the formula (I) is one of the formulas (II) or (III) acts. 9. Recording material according to claim 9, characterized in that that the magenta coupler of the formula (I) is one of the formula (II) acts. 10. Recording material according to claim 9, characterized in that that the magenta coupler of the formula (I) is one of the formula (III) acts. 11. Recording material according to claim 1, characterized in that that the coefficient of variation of the monodisperse emulsion is not greater than 0.15. 12. Recording material according to claim 11, characterized in that that the average grain size of the monodisperse emulsion of at least 0.25 m reaches a maximum of 0.75 µm. 13. Recording material according to claim 11, characterized in that that the monodisperse emulsion is a silver halide emulsion of gelatin or a gelatin derivative and silver halide grains containing less than 1 mol% silver iodide, not less than 5 mol% silver chloride and the remainder silver bromide.