Colour photographic recording material containing a dye releasing compound for cyan dyes and a colour image produced with these dyes

Dye releasing compounds which release dyes corresponding to formula I ##STR1## wherein R.sup.1 denotes alkyl, aryl, arylamino, alkoxy or aryloxy, PA0 R.sup.2 denotes H or halogen, PA0 R.sup.3 denotes alkyl with 2-4 carbon atoms, PA0 R.sup.4 denotes H or one or more substituents such as alkyl, alkoxy, acylamino or halogen, including a substituent in the ortho-position to the group ##STR2## which together with R.sup.5 completes a cyclic amino group, R.sup.5 denotes alkyl with up to 4 carbon atoms or a group which together with a subsituent denoted by R.sup.4 or together with R.sup.6 completes a cyclic amino group, and PA0 R.sup.6 denotes alkyl with up to 4 carbon atoms or a group which together with R.sup.5 completes a cyclic amino group are suitable for the production of light-stable cyan colour images.

This invention relates to a colour photographic recording material for the 
production of colour images by the dye diffusion transfer process 
containing a non-diffusible, colour providing compound (dye releasing 
compound) in association with at least one light-sensitive silver halide 
emulsion layer, which compound releases a diffusible cyan dye on 
development. 
The basic principle on which the dye diffusion process operates is that 
when development takes place, an imagewise distribution of diffusible dyes 
is produced in a light-sensitive element in accordance with a previous 
exposure and is transferred to an image receptor element. 
It is very important in this process that the dyes should be fixed 
sufficiently firmly in the image receptor layer and that they should have 
excellent spectral properties and stability to light and heat. 
Cyan dyes for the dye diffusion process containing a phthalocyanine group 
as chromophore, preferably in the form of the copper complex, have been 
disclosed, for example, in DE-A-3 101 036. 
One disadvantage of these extremely stable dyes is that they are less 
diffusible than the yellow and magenta dyes conventionally used, with the 
result that a colour shift from red to neutral gradually takes place in 
the course of the colour transfer and the optimum transfer time must be 
strictly observed. 
Rapidly diffusible cyan dyes for the dye diffusion process have been 
described among the series of 4-(4-nitrophenylazo)-1-naphthols, e.g. in 
DE-A-2 406 653 and DE-A-2 853, 584. 
The dyes mentioned in DE-A-2 406 653 exist in the form of an anionic 
chromophore after the carrier group which confers diffusion reistance has 
been split off, and in this form the dyes diffuse into the image receptor 
layer and are fixed on the mordant in the form of the dye anion. Anionic 
dyes generally have little fastness to light. It is therefore not 
surprising that the cyan anionic dyes from the series of 
4-(4-nitrophenylazo)naphthols have insufficient fastness to light. With a 
view of overcoming this disadvantage, dyes from the same class but with 
improved light-fastness due to an additional carbamoyl substitution in the 
ortho-position to the OH group have been described in DE-A-2 853 584. 
These more light-stable dyes, however, in many cases have an absorption 
for wavelengths which are too short or an absorption range which is too 
wide and/or their side absorption is too high, and these various factors 
generally impair the colour reproduction. 
Another feature common to these dyes is that their susceptibility to attack 
by reducing agents is increased by the presence of a nitro group in the 
para-position to the azo group. Quite apart from developer substances, 
however, reducing agents are present in virtually all recording materials 
used in dye diffusion transfer processes to fulfil certain functions. For 
example, the interlayers between the individual layer packets associated 
with different partial colours normally contain reducing agents, in 
particular from the series of mono- or dialkylated hydroquinones, which 
are the purpose of trapping developer oxidation products and are 
accordingly highly reactive. 
Furthermore, recording materials which contain reducible dye releasing 
compounds have so-called electron donor compounds (ED compounds) or their 
precursors associated with these dye releasing compounds. This is 
described in the following Applications: EP-A-0 004 399, U.S. Pat. No. 
4,139,379, U.S. Pat. No. 4,278,750, DE-A-3 014 699, EP-A-0 038 092, DE-A-3 
008 588 and DE-A-3 006 268. 
It is known that 4-nitrophenylazo dyes are more readily attacked by 
reducing agents than other monoazo dyes. Even the brief contact between 
reducing agent and chromophore during the time of formation of the image 
may be sufficient in the presence of a strongly alkaline processing medium 
to change the cyan dye to compounds of an unknown structure which absorb 
light in a shorter wavelength region so that the colour shade changes from 
cyan to blue or even violet. 
It is therefore desirable for the purpose of the dye diffusion process to 
provide readily diffusible cyan dyes which do not contain a 
4-nitrophenylazo group and are therefore less readily reduced. 
The light fastness of dyes, in particular of azo dyes, may in many cases be 
increased by complex formation with polyvalent metal ions. If this complex 
formation is carried out subsequently, i.e. after release of the dyes from 
the dye releasing compound, then it is not always possible to avoid 
discolouration of the recording material or of the image receptor layer by 
the free metal ions. 
Diffusible forms of indoaniline dyes known from chromogenic colour 
photography have also been described as suitable cyan dyes for the dye 
diffusion process. 
Descriptions of such dyes are given, for example, in U.S. Pat. No. 
3,227,550, e.g. the couplers XXIII and XXVIII. One disadvantage of these 
compounds is that if the colour developer required for development is 
present in excess, this excess is not removed and impairs the whites by 
brown discolouration when the image is kept in storage. The known cyan 
dyes of this type are also insufficiently stable to light. 
Indoaniline dyes may also be prepared from the corresponding leuco dyes by 
oxidation without requiring colour developers. This oxidation may be 
brought about, for example, by a reaction of the leuco dyes with the 
oxidation products of an auxiliary developer. 
Owing to the sensitivity of leuco dyes to oxidation, photographic recording 
materials of this kind have a considerable tendency to fogging. Moreover, 
the dye diffusion process requires the use of additional silver halide to 
bring about not only imagewise mobility of the dye but also oxidation of 
the leuco dye. 
The use of azomethine and indoaniline dyes in the dye diffusion process is 
also made more difficult by the fact that the dyes are readily destroyed 
by hydrolysis at the high pH levels required for dye release and diffusion 
so that weaker and blackened colours are obtained. 
It is an object of the present invention to provide new colour providing 
compounds for the dye diffusion transfer process, from which diffusible 
cyan dyes which have improved light fastness, improved spectral properties 
and improved resistance to alkalies and reducing agents are released in 
the course of photographic development. 
The present invention relates to a colour photographic recording material 
for the production of colour images by the dye diffusion transfer process, 
in which a nondiffusible, colour providing compound (dye releasing 
compound) is associated with at least one light-sensitive silver halide 
emulsion layer, a diffusible cyan dye being released from this compound 
under the conditions of alkaline development as a function of the 
development of the silver halide emulsion layer, characterised in that the 
cyan dye corresponds to the following formula I: 
##STR3## 
wherein R.sup.1 denotes alkyl, aryl, arylamino, alkoxy or aryloxy, 
R.sup.2 denotes H or halogen, 
R.sup.3 denotes alkyl with 2 to 4 carbon atoms, 
R.sup.4 denotes H or one or more substituents such as alkyl, alkoxy, 
acylamino or halogen, including a substituent in the ortho-position to the 
group 
##STR4## 
which substituent combines with R.sup.5 to complete a cyclic amino group, 
R.sup.5 denotes alkyl with up to 4 carbon atoms or a group which together 
with a substituent denoted by R.sup.4 or together with R.sup.6 completes a 
cyclic amino group, and 
R.sup.6 denotes alkyl with up to 4 carbon atoms or a group which together 
with R.sup.5 completes a cyclic amino group. 
An alkyl group denoted by R.sup.1, R.sup.4, R.sup.5 or R.sup.6 or contained 
in the alkoxy or acylamino substituents denoted by R.sup.4 preferably 
contains 1 to 4 carbon atoms. It may be straight chained or branched and 
may in turn be substituted, e.g. by halogen, hydroxyl, alkoxy, aroxy or 
acylamino. The alkyl group denoted by R.sup.3 preferably is ethyl or 
isopropyl. 
An aryl or arylamino group denoted by R.sup.1 is preferably a phenyl or 
aniline group which may be substituted by halogen, CN, alkyl, alkoxy, 
alkylsulphonyl or alkylsulphamoyl. 
The cyclic amino group mentioned in the definition or R.sup.4, R.sup.5 and 
R.sup.6 is a 5-, 6-, or 7-membered cyclic amino group, which if it is 
formed by R.sup.4 and R.sup.5, is condensed on a benzene ring. Examples 
are the pyrrolidine, piperidine, morpholine and indolenine group. 
An acyl group (acylamino) is preferably derived from aliphatic carboxylic 
or sulphonic acids containing up to 4 carbon atoms. 
The dyes of formula I also have suitable functional groups for adjusting 
the diffusion and mordanting properties, e.g. in the form of the groups 
mentioned as substituents or in the form of substituents which may be 
attached to one of these groups through a suitable connecting member. 
Examples of these functional groups include anionic and anionisable groups 
such as sulphonate, sulphinate, phenolate, naphtholate, carboxylate, 
disulphimide and sulphamoyl groups. In addition, the dyes of formula I 
contain a functional group obtained by the opening of a bond on a carrier 
group which contains a ballast group, this functional group being 
characteristic of the carrier group and the linkage by which it is 
attached to the carrier group. The last mentioned functional group may be 
identical with one of the above mentioned groups which modify the 
diffusion and mordanting characteristics. The said functional group may, 
for example, be attached to an alkyl or aryl group which may in turn form 
part of one of the above mentioned groups and is preferably a component of 
R.sup.1. 
Formula I denotes the diffusible dyes according to this invention, 
optionally released in the course of development. These dyes may be 
released, for example, from the corresponding non-diffusible, colour 
providing compounds (dye releasing compounds) incorporated in the layer. 
These are compounds in which, for example, a dye residue corresponding to 
formula I is attached to a carrier group CAR containing at least one 
ballast group, optionally with the interposition of a suitable connecting 
member. 
The member through which the dye of formula I is attached to the carier 
group may be, for example, one of the substituents R.sup.1 to R.sup.6. The 
dye releasing compounds according to the invention may therefore be 
represented, for example, by the following formula II 
##STR5## 
wherein R.sup.1 -R.sup.6 have the meanings already indicated, 
CAR denotes a carrier group containing at least one group which confers 
diffusion resistance, 
and the broken line represents a possible linkage. 
In the dye releasing compounds according to the invention corresponding to 
formula II, therefore, the carrier group is contained as a substituent in 
one of the groups R.sup.1 to R.sup.6, preferably in R.sup.1 or R.sup.6. 
In addition to containing a ballast group, the carrier group represented by 
CAR contains at least one group which can be split off as a function of 
the development of a silver halide emulsion layer so that the dye attached 
to the carrier group can be separated from the ballast group, possibly 
together with a small fragment of the original carrier group, and can 
thereby be released from its attachment to the layer. The carrier groups 
may vary in structure according to the function of the releasable group. 
The dye releasing compounds according to this invention may be any of 
numerous types of compounds which are all distinguished by a connecting 
member which is redox dependent in the strength of its attachment and 
which links a dye residue to a carrier group containing a ballast group. 
See in this connection a summarizing account of this field in Angew. Chem. 
Int. Ed. Engl. 22 (1983), 191-209, in which the most important of the 
known systems are described. 
Particularly advantageous compounds of this kind are redox active dye 
releasing compounds corresponding to the formula 
EQU BALLAST--REDOX--DYE 
wherein 
BALLAST: denotes a ballast group, 
REDOX: denotes a redox active group, i.e. a group which is oxidizable or 
reducible under the conditions of alkaline development and which can 
undergo varying degrees of an elimination reaction, a nucleophilic 
displacement reaction, hydrolysis or some other decomposition reaction, 
depending on whether it is present in the oxidized or the reduced state, 
the said reactions resulting in the release of the DYE residue, and 
DYE: denotes the residue of a diffusible dye, in the present case a dye 
corresponding to formula I. 
Ballast groups enable the dye releasing compounds according to the 
invention to be incorporated in a diffusion fast form in the hydrophilic 
colloids normally used in photographic materials. They are preferably 
organic groups, generally straight chained or branched aliphatic groups 
with generally 8 to 20 carbon atoms, optionally containing carbocyclic or 
heterocyclic, optionally aromatic groups. These ballast groups may be 
attached to the remaining part of the molecule either directly or 
indirectly, e.g. through one of the following groups: NHCO, NHSO.sub.2, NR 
(in which R denotes hydrogen or alkyl), O or S. The ballast group may in 
addition contain water-solubilizing groups, e.g. sulpho or carboxyl 
groups, and these may also be present in an anionic form. Since the 
diffusion characteristics depend on the molecular size of the whole 
compound, it is sometimes sufficient, e.g. if the molecule as a whole is 
large enough, to use shorter chained groups as ballast groups. 
Redox active carrier groups having the structure BALLAST-REDOX- and 
corresponding dye releasing compounds are known in various forms. A 
detailed description need not be given here in view of the comprehensive 
article in Angew. Chem. Int. Ed. Engl. 22 (1983) 191-209. 
Some examples of redox active carrier groups from which a dye residue is 
split off according to a previous imagewise oxidation or reduction are 
shown below purely for illustration: 
##STR6## 
The groups in brackets are functional groups of the dye residue and are 
separated together with this residue from the remaining part of the 
carrier group. The functional group may be one of the substituents 
mentioned in the definition of the groups R.sup.1 to R.sup.6 in formulae I 
and II and may have a direct influence on the absorption properties of the 
released dye. On the other hand, the functional group may be separated 
from the chromophore of the dye by an intermediate or linking member if it 
is present as substituent in one of the groups R.sup.1 to R.sup.6 and need 
not have any influence on the absorption properties. Lastly, the 
functional group may be of some importance together with the intermediate 
member in influencing the diffusion, mordanting and stability properties 
of the released dye. Alkylene and arylene groups, for example, may be 
suitable intermediate members. 
Suitable dye releasing compounds have been described in the following: U.S. 
Pat. Nos. 3,227,550; 3,443,939; 3,443,940; DE-A-1 930 215, DE-A-2 242 762, 
DE-A-2 402 900, DE-A-2 406 664, DE-A-2 505 248, DE-A-2 543 902, DE-A-2 613 
005, DE-A-2 645 656, DE-A-2 809 716, DE-A-2 823 159, DE-A-861 241, EP-A-0 
004 399, EP-A-0 004 400, DE-A-3 008 588, DE-A-3 014 669, EP-A-0 038 092. 
The dye releasing compounds may be oxidizable or capable of coupling in 
some embodiments of the recording material of the present invention while 
in others it may be present in a reducible form. When a conventional 
negative silver halide emulsion is used, the copy obtained from the 
original may be a negative or a positive, depending on whether the dye is 
released from the oxidized or the reduced form of dye releasing compound. 
It is therefore possible to obtain positive or negative images as desired 
by suitable choice of the dye releasing systems. 
For producing positive colour images from positive original by means of 
negative silver halide emulsions it is suitable to use, for example, a 
recording material according to the invention containing reducible dye 
releasing compounds with a carrier group corresponding to the following 
formula: 
##STR7## 
wherein R.sup.1' denotes alkyl or aryl, 
R.sup.2' denotes alkyl, aryl or a group which together with R.sup.3' 
completes a condensed ring, 
R.sup.3' denotes hydrogen, alkyl, aryl, hydroxyl, a halogen such as 
chlorine or bromine, amino, alkylamino or dialkylamino, including cyclic 
amino groups (such as piperidino or morpholino), acylamino, alkylthio, 
alkoxy, aroxy, sulpho or a group which together with R.sup.2' completes a 
condensed ring, 
R.sup.4' denotes alkyl and 
R.sup.5' denotes alkyl or, preferably, hydrogen, 
and at least one of the groups R.sup.1' to R.sup.4' contains a ballast 
group. 
The preparation of indoaniline dyes according to the invention 
corresponding to formula I and of dye releasing compounds corresponding to 
formula II is normally carried out in several steps, one of which forms 
the linkage to the carrier group which confers diffusion resistance while 
another is concerned with the synthesis of the chromophore. 
The chromophore is generally produced by a process of chromogenic coupling 
in which conventional colour developer compounds are reacted in the 
presence of an oxidizing agent with a compound corresponding to the 
following formula III 
##STR8## 
wherein R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated above and 
X denotes hydrogen or a group which can be split off in this reaction, 
e.g. halogen, alkoxy or alkylthio. 
Attachment to the carrier group may be carried out by basically known 
methods, either before or after formation of the chromophore. 
The attachment may be effected either through the coupler residue or 
through the colour developer residue, provided these residues carry the 
appropriate function for the reaction with the carrier residue. The 
functions required depend, of course, on the group in the carrier residue 
which is to enter into a reaction with such a function. The functions may 
be, for example, amino groups, hydroxy groups, sulphonic acid chloride 
groups, sulphinic acid groups, carboxylic acid groups, carboxylic acid 
chloride groups, etc. 
Examples of cyan dyes (C-) according to the invention are shown below. 
Compounds marked by an asterisk (*) are model dyes. 
##STR9## 
Dye releasing compounds (FA-) according to the invention are shown below: 
##STR10## 
Methods of synthesis of the dye releasing compounds according to the 
invention are illustrated below by way of example: 
a. 4-Nitrophenoxyacetyl-(2-hydroxy-3,5-dichloro-4-ethylanilide) 
41.2 g (0.2 mol) of 2-hydroxy-3,5-dichloro-4-ethylaniline were dissolved in 
250 ml of acetone and 24.3 ml of pyridine and cooled to 
0.degree.-5.degree. C. 4.3 g (0.2 mol) of 4-nitrophenoxy-acetic acid 
chloride were added and the reaction mixture was stirred for one hour. 
After the addition of 500 ml of water, the mixture was suction filtered 
and washed with water. The residue was heated to boiling in 250 ml of 
water to 250 ml of methanol, cooled, suction filtered and again washed 
with water and methanol. It was then heated to boiling with 350 ml of 
acetone, cooled, suction filtered, washed with acetone and dried. 
b. 
##STR11## 
34.6 g (0.09 mol) of the product obtained under a. and 39.4 g (0.09 mol) of 
4-amino-3-methyl-(N-ethyl-N-.beta.-methylsulphonylaminoethyl-aniline 
sulphate were stirred in 500 ml of methanol, and 135 ml of a 30% sodium 
methanolate solution (0.73 mol) were added. A solution of 44.5 g (0.19 
mol) of ammonium persulphate in 100 ml of water and 200 ml of methanol was 
added dropwise at 20.degree.-25.degree. C. The reaction mixture was 
stirred for one hour, suction filtered, washed with methanol and dried. 
c. Dye releasing compound FA-1. 
16.5 g of the compound obtained under b. were stirred together with 300 ml 
of glacial acetic acid until a homogeneous suspension was obtained. 36 g 
of zinc dust were added in four portions at 40.degree.-50.degree. C. After 
reduction has been completed, the residue was suction filtered and washed 
with glacial acetic acid. 300 ml of 5N-sodium hydroxide solution were 
slowly added to the glacial acetic acid solution with cooling to 
15.degree.-20.degree. C. and the reaction mixture was extracted 5 times by 
shaking with methylene chloride (150 ml, 100 m, 50 ml, 50 ml and 50 ml). 
The methylene chloride phase was washed with 1% sodium dithionite 
solution, dehydrated with sodium sulphate and filtered. To this solution 
was added a solution of 16.5 g of the sulphochloride corresponding to 
formula 
##STR12## 
in 70 ml of methylene chloride. 41 ml of pyridine were then added and the 
reaction mixture was stirred for one hour. At this stage, the dye residue 
present in the form of a leuco dye oxidized to the indoaniline dye. After 
removal of the solvent, the smeary residue was treated with water twice on 
a steam bath and the lumps obtained on cooling were broken down in water, 
suction filtered, washed with water and dried. 
28 g of the resulting crude product were chromatographed on a silica gel 
column, using a 97:3 mixture of methylene chloride and methanol. The 
fraction containing the product was freed from solvent and the residue was 
boiled with 120 ml of ethanol, suction filtered when cold, washed with 
ethanol and dried. Yield: 5.1 g of dye releasing compound FA-1. 
When the dye releasing compounds according to the present invention are 
developed, they give rise to diffusible dyes which produce a cyan colour 
image in the image receptor layer. This image has excellent light fastness 
and stability to heat, moisture and alkali and is less sensitive to 
reducing agents. 
Colour photographic recording materials for the production of multicolour 
images normally contain colour providing compounds in spatial and spectral 
association with the silver halide emulsion layers of the different 
spectral sensitivities. These colour providing compounds serve to produce 
the various partial colour images in cyan, magenta and yellow and in the 
present case consist in particular of dye releasing compounds. 
By "spatial association" is meant that the dye releasing compound is in 
such a spatial relationship to the silver halide emulsion layer that the 
two layers are capable of interacting to produce an imagewise correlation 
between the silver image formed on development and the colour image 
produced from the dye releasing compound. This is generaly achieved by 
arranging the dye releasing compound in the silver halide emulsion layer 
or in an adjacent layer of binder which may be light insensitive. 
By "spectral association" is meant that the spectral sensitivity of each of 
the light-sensitive silver halide emulsion layers and the colour of the 
partial colour image produced from the dye releasing compound which is 
spatially associated with the given silver halide emulsion layer have a 
certain relationship to one another so that each of the spectral 
sensitivities (red, green, blue) is associated with a different colour of 
the particular partial colour image (in general, for example, the cyan, 
magenta and yellow in this sequence). 
One or more dye releasing compounds may be associated with each of the 
differently spectrally sensitized silver halide emulsion layers. The dye 
releasing compounds according to the invention corresponding to formula II 
preferably have a red-sensitized silver halide emulsion layer associated 
with them. 
If the dye releasing compound is oxidizable then it is itself a reducing 
agent which is oxidized by the imagewise exposed silver halide, either 
directly or indirectly with the aid of electron transfer agents (ETA). 
This results in an imagewise differentiation in the capacity to release 
the diffusible dye. If, on the other hand, the dye releasing compound is 
reducible, then it is advantageously used in combination with a limited 
quantity of reducing agent, a so-called electron donor compound or an 
electron donor precursor compound which is present in the same layer of 
binder as the dye releasing compound and the light-sensitive silver 
halide. The presence of an electron transfer agent may also be 
advantageous when reducible dye releasing compounds are used in 
combination with electron donor compounds. 
The electron donor compound used in combination with a reducible dye 
releasing compound acts as reducing agent both for the silver halide and 
the dye releasing compound. Since the silver halide and the dye releasing 
compound must to some extent compete with each other for the oxidation of 
the electron donor compound but the silver halide is more powerful than 
the dye releasing compound in this reaction, the silver halide becomes the 
determining factor, depending on its previous imagewise exposure, for the 
areas of image within which the dye releasing compound will be converted 
into its reduced form by the electron donor compound. 
Under the conditions of development, the electron donor compound which is 
present in limited quantity is oxidized by the light-sensitive silver 
halide under the catalytic action of the latent image nuclei produced by 
exposure in the silver halide and therefore according to the amount of 
exposure which has taken place, and it is then no longer available for a 
reaction with the dye releasing compound. An imagewise distribution of 
unused electron donor compound is then obtained. 
Compounds which have been described as electron donor compounds include, 
for example, non-diffusible or only slightly diffusible derivatives of 
hydroquinone, of benzisoxazolone, of p-aminophenol and of ascorbic acid 
(e.g. ascorbyl palmitate) (DE-A-2 908 716). 
Other examples of electron donor compounds have been disclosed in DE-A-2 
947 425, DE-A-3 006 268, DE-A-3 130 842, DE-A-3 144 037, DE-A-3 217 877 
and EP-A-0 124 915 and in Research Disclosure 24 305 (July 1984). 
Particularly suitable are those electron donor compounds which are formed 
from their precursor compounds in the layer itself under the conditions of 
development, i.e. electron donor compounds which before development are 
present in a virtually inactive, masked form in the recording material. 
These initially inactive electron donor compounds are then converted into 
their active form under the conditions of development, for example by the 
removal of certain protective groups by hydrolysis. In the present case, 
the term "electron donor compound" also includes these electron donor 
precursor compounds. 
Although a wide variety of methods is available for incorporating the dye 
releasing compounds according to the invention, it has been found 
advantageous to incorporate the dye releasing compounds of the present 
invention in the layers in the form of emulsions by means of so-called oil 
formers. This has the advantage, particularly when dye releasing compounds 
which are reducible and decomposable by reduction are used in combination 
with ED compounds, that the dye releasing compounds and the ED compounds 
can be brought into very close functional contact in the form of a common 
emulsion. Suitable oil formers are described, for example, in U.S. Pat. 
No. 2,322,027, DE-A-1 772 192, DE-A-2 042 659 and DE-A2 049 689. The 
optimum quantities of dye releasing compound and, if used, of ED compound 
to be incorporated may be determined by simple routine tests. The dye 
releasing compound of the present invention may be used, for example, in 
quantities of 0.05 to 0.2 mol per mol of silver halide and the ED 
compound, if used at all, in quantities of 0.1 to 0.6 mol per mol of 
silver halide. 
The light-sensitive silver halide emulsions may be emulsions of silver 
chloride, silver bromide or mixtures thereof, possibly with a small silver 
iodide content of up to 10 mol-% and they may be used in one of the usual 
hydrophilic binders. The emulsions may also contain organic or other 
inorganic silver salts in addition to the light-sensitive silver halides, 
especially in heat-developable colour photographic recording materials. 
These additional silver salts are on the whole light-insensitive or at 
least very much less sensitive than the silver halides. Suitable organic 
silver salts include, for example, the salts of carboxylic acids, such as 
silver behenate, or the salts of imino compounds, such as silver 
benzotriazolate. The binder used for the photographic layers is preferably 
gelatine but this may be partly or completely replaced by other natural or 
synthetic binders. 
The emulsions may be chemically and/or spectrally sensitized in the usual 
manner. They may also be stabilized with suitable additives. Suitable 
chemical sensitizers, spectral sensitizing dyes and stabilizers are 
described, for example, in Research Disclosure 17643; see in particular 
Chapters III, IV and VI. 
The usual hydrophilic film formers of natural or synthetic origin may be 
used as protective colloids or binders for the layers of the recording 
material, e.g. proteins, in particular gelatine. Casting auxiliaries and 
plasticizers may also be used. See Research Disclosure 17643, Chapters IX, 
XI and XII. 
The layers of binder may be hardened in the usual manner, using comppounds 
which react with reactive groups in the binder, such as amino groups, 
carbonyl groups or active methylene groups, to give rise to cross-linking 
of the binder. Examples include formaldehyde, dialdehydes, 
.alpha.-diketones, compounds containing active halogen atoms, compounds 
containing oxirane or aziridine groups, compounds containing active vinyl 
groups such as acryloyl groups or vinyl sulphone groups, and the so-called 
carboxyl-activating hardeners such as isoxazolium salts, formadinium 
salts, carbodiimide compounds, carbamoyl pyridinium salts and carbamoyl 
oxypyridinium salts; see Research Disclsoure 17643, Chapter X. The 
hardeners may be used singly or as mixtures. 
Development of the imagewise exposed colour photographic recording material 
according to the invention may be initiated by treating the recording 
material with an aqueous-alkaline, possibly highly viscous developer 
solution. In that case, the auxiliary developer compounds required for 
development are either present in the developer solution or partly or 
completely contained in one or more layers of the colour photographic 
recording material according to the invention. When development takes 
place, diffusible dyes are released imagewise from the dye releasing 
compounds and are then capable of being transferred to an image receptor 
layer which may be an integral part of the colour photographic recording 
material of this invention or it may be in contact with its material, at 
least during the development time. The image receptor layer may therefore 
be arranged on the same layer support as the light-sensitive element or on 
a separate layer support. It consists mainly of a binder containing the 
mordant for fixing the diffusible dyes released from the non-diffusible 
dye releasing compounds. The mordants used for anionic dyes are preferably 
long chained quaternary ammonium or phosphonium compounds, e.g. those 
described in U.S. Pat. No. 3,271,147 or in U.S. Pat. No. 3,271,148. 
Certain metal salts and their hydroxides which form difficultly soluble 
compounds with the acid dyes may also be used. Polymeric mordants may also 
be suitable, for example those described in DE-A-2 315 304, DE-A-2 631 521 
or DE-A-2 941 818. The dye mordants are contained in the mordant layer as 
dispersions in one of the usual hydrophilic binders such as gelatine, 
polyvinyl pyrrolidone, or partially or completely hydrolysed cellulose 
esters. Some binders may, of course, function as mordants, e.g. polymers 
of nitrogen-containing, optionally quaternary bases, such as 
N-methyl-4-vinylpyridine, 4-vinylpyridine or 1-vinylimidazole, as 
described, for example, in U.S. Pat. No. 2,484,430. Further examples of 
suitable mordanting binders include guanyl hydrazone derivatives of alkyl 
vinyl ketone polymers such as those described, for example, in U.S. Pat. 
No. 2,882,156, or guanyl hydrazone derivatives of acylstyrene polymers as 
described, for example, in DE-A-2 009 498. The last-mentioned mordanting 
binders would, however, generally be used together with other binders, 
e.g. gelatine. 
If the image receptor layer is to be kept in contact with the 
light-sensitive element after development, then an alkali permeable, 
light-reflecting layer of binder containing pigment is generally placed 
between these two layers to serve as optical separation between the 
negative and positive and as aesthetically attractive image background for 
the transferred colour image. Such a light-reflecting layer may already be 
preformed in the light-sensitive colour photographic recording material in 
known manner or it may be produced in the course of development, also in 
known manner. If the image receptor layer is arranged between the layer 
support and the light-sensitive element and is separated from the latter 
by a preformed light-reflecting layer, then the layer support must either 
be transparent so that the colour transfer image produced can be viewed 
through this layer or the light-sensitive element together with the 
light-reflecting layer must be removed from the image receptor layer to 
expose the latter. Alternatively, the image receptor layer may be arranged 
as the uppermost layer in an integral colour photographic recording 
material, in which case the material may be exposed through the 
transparent layer support. 
After the photographic process, the image receptor layer contains an 
imagewise distribution of cyan monoazo dyes corresponding to formula I. 
The dye releasing compound of formula II associated with the originally 
light-sensitive silver halide emulsion layer is also present in imagewise 
distribution after processing but as the complementary to the transferred 
dye image, and may also be used as colour image in known manner (retained 
image). 
In another embodiment, the colour photographic recording material according 
to the present invention may constitute a heat developable recording 
material. In that case, development is initiated by a heat treatment and 
treatment with aqueous baths is generally obviated. In this embodiment, 
the reactants required for development are contained in one or more layers 
of the recording material. This applies in particular to development 
agents, bases or base precursors and so-called thermal solvents or melt 
formers; see Research Disclosure 17029 (June 1978). 
Development of the imagewise exposed colour photographic recording material 
according to the invention includes, for example in the case of the 
thermal development process, the steps of silver halide development, 
production of an imagewise distribution of diffusible dyes and transfer of 
this imagewise distribution to the image receptor layer by diffusion. This 
development is initiated by subjecting the exposed recording material to a 
heat treatment in which the light-sensitive layer of binder is heated to a 
temperature e.g. in the region of 80.degree. to 250.degree. C. for a time 
of about 0.5 to 300 seconds. Suitable conditions are thereby provided in 
the recording material for the development processes, including dye 
diffusion, without any need for a liquid medium, e.g in the form of a 
developer bath. Development releases diffusible dyes in imagewise 
distribution from the dye releasing compounds and transfers them to an 
image receptor layer which may be an integral constituent of the colour 
photographic recording material according to the invention or is in 
contact with this material, at least during the development time. 
Imagewise development of silver, release of dye and transfer of colour thus 
take place synchronously in a single step development process. 
Production of the clour image with the colour photographic recording 
material according to the invention may also take place as a two-step 
development process in which silver halide development and release of dye 
take place in the first step at temperatures in the range of 80.degree. to 
250.degree. C. and transfer of colour image from the light-sensitive part 
to an image receptor part in contact therewith is then carried out in a 
second step, e.g. by heating to a temperature of 50.degree. to 150.degree. 
C., preferably to 70.degree.-90.degree. C., in which case diffusion aids 
(solvents) such as water may be applied externally before the 
light-sensitive part is laminated to the image receptor part.

EXAMPLE 1 
Dye C-2 according to the invention (Model dye) and dye V-1 which is not 
according to the invention and corresponds to the following formula 
##STR13## 
were each dissolved separately in a small quantity of methyl ethyl ketone 
and excess 1N KOH was then added to each solution at 20.degree. C. This 
resulted in gradual destruction of the dye, which could be followed by the 
reduction in colour density. The following values were found for the half 
life t.sub.1/2 of the dye decomposition, measured at the absorption 
maxima: 
______________________________________ 
.gamma..sub.max [nm] 
t.sub.1/2 [min] 
______________________________________ 
Dye C-2 676 24 
Dye V-1 668 13 
______________________________________ 
This means that the dye according to the invention is more stable to 
hydrolysis by factor of almost 2. Under the processing conditions normally 
employed for the dye diffusion process, the cyan dyes according to the 
invention need not be expected to undergo any detectable decomposition. 
EXAMPLE 2 
A photographic recording material according to this invention consisting of 
a light sensitive part (A) and an image receptor part (B) were prepared as 
described below. The quantities given refer in each case to 1 m.sup.2. 
Part A consisted of a polyethylene terephthalate support to which the 
following layers were applied in succession: 
1. A light-sensitive, red-sensitized silver bromide emulsion corresponding 
to 0.5 g AgNO.sub.3 and a light-insensitive organic silver salt in the 
form of silver benzotriazolate corresponding to 0.5 g of AgNO.sub.3, 
together with 0.648 g of dye releasing compound FA-1, according to the 
invention, 0.283 g of compound ED-1 (electron donor compound), 0.931 g of 
palmitic acid diethylamine and 0.931 g of gelatine. 
2. An auxiliary layer containing 1.5 g of guanidine trichloroacetate, 0.24 
g of 4-hydroxymethyl-4-methylphenidone, 0.028 g of the compound 
corresponding to the formula 
##STR14## 
and 1.5 g of gelatine. 
3. A hardening layer consisting of an instant hardener and 0.5 g of 
gelatine. 
Part B consisted of a polyethylene coated support carrying the following 
layers one above the other: 
1. A mordant layer containing 3.0 g of a polyvinylimidazole quaternized to 
an extent of 5% with chloroethanol, and 3 g of gelatine 
2. A covering layer containing 1 g of gelatine and 0.35 g of 
dimethylolurea. 
The light-sensitive material was exposed behind a grey wedge and uniformly 
heated to 120.degree. C. for one minute. This element was then laminated 
with its active side to the image receptor part B which had previously 
been left to soak in water for 10 seconds, and the two layers were kept in 
contact at 70.degree. C. for 2 minutes. The dye receptor sheet was then 
separated from the light-sensitive part. 
Another light-sensitive part was prepared according to the state of the art 
for comparison. This part contained 0.33 g of dye releasing compound V-2 
(not according to the invention) instead of the dye releasing compound 
FA-1 according to the invention. The two cyan wedges obtained were 
examined for their colour brilliance and stability to light. 
______________________________________ 
Side densities (standardized to cyan density = 1.0) 
______________________________________ 
according to the invention 
yellow: 0.26 
magenta 0.44 
comparison yellow: 0.28 
magenta 0.48 
______________________________________ 
Regression in colour density at density 0.5 after 10.sup.7 Lux.h according 
to the invention: 17%, comparison: 57%. 
The dye obtained from the compound according to the invention thus had a 
substantially higher stability to light with at least equal colour 
brilliance. 
##STR15## 
EXAMPLE 3 
The light-sensitive part of a part of a recording material was prepared by 
the method described in Example 2 but without any guanidine 
trichloroacetate in layer 2. 
After exposure, this light-sensitive part was laminated with its active 
side to an image receptor sheet which had been prepared as described in 
Example 2 but had previously been soaked for one minute in a 4% aqueous 
NaOH solution. the sheets were separated after a contact time of 2 minutes 
at 30.degree. C. An imagewise transfer of the dye with brilliant colour 
was obtained in the image receptor sheet. 
This proves that when treated with aqueous alkali, the dye according to the 
invention attains its full colour density and colour brilliance without 
being destroyed by hydrolysis.