Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Two or more radiation-sensitive layers containing other than...
Reexamination Certificate
1999-12-14
2001-05-08
Schilling, Richard L. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Two or more radiation-sensitive layers containing other than...
C430S214000, C430S507000, C430S551000
Reexamination Certificate
active
06228568
ABSTRACT:
The present invention relates to a colour photographic recording material which contains, in at least one layer between the substrate and the light-sensitive emulsion layer situated nearest to the substrate, a compound of formula (I)
wherein
X and Y, independently of each other in each case, represent an electron-attracting group, and X and Y together can form a group which is necessary for the completion of a 5- or 6-membered ring.
If the spectral composition of the light which is incident on a light-sensitive photographic silver halide emulsion layer has to be checked or controlled, a coloured layer can be incorporated in the light-sensitive photographic recording material for this purpose, and this layer is then termed a filter layer. Thus in colour photographic materials, for example, a yellow coloured filter layer is generally disposed between the blue-sensitive layer and the green-sensitive and red-sensitive layers situated below the blue-sensitive layer, in order to keep blue light away from the green- and red-sensitive layers.
Stringent demands are made on dyes used in photographic materials. They not only have to exhibit a suitable spectral absorption corresponding to their purpose of use, but should also be photochemically inert. In particular, these dyes must have no disadvantageous effects on the quality of the photographic silver halide emulsion; thus they must not, for example, depress the film speed or give rise to the formation of fogging. Moreover, although the dyes in the material should be resistant to diffusion, they have to be completely and irreversibly decolorised or washed out of the layer during the processing of the material, so that no unwanted coloration remains on the exposed, developed photographic material. Furthermore, the dyes themselves should be stable on storage and should not give rise to any change in the photographic material during storage.
These requirements are not fulfilled to a satisfactory extent by known dyes. The colloidal silver which is usually employed in yellow filter layers readily gives rise to the formation of fogging in adjacent emulsion layers. Water-soluble organic dyes which are rendered diffusion-resistant by the introduction of long alkyl chains, such as those disclosed in DE 22 59 746 for example, are not decolorised or are only incompletely decolorised in normal photographic processing baths. When dyes are fixed with a mordant, as in GB 1 034 044, U.S. Pat. No. 3,740,228 or DE-A-29 41 819 for example, the effect of the mordant is generally insufficient to fix the dye to the requisite extent in the mordant layer.
Condensation products of 3-alkylisoxazolones with p-N,N-Bis-carbalkoxy-methyl-aminobenzaldehydes or N-carbalkoxyethylcarbazol-3-aldehydes (arylidene dyes) are known from DE 196 46 402 which exhibit a suitable absorption for use as yellow filter dyes and which are completely decolorised in the layer during development.
It has been shown, however, that even the yellow filter dyes according DE 196 46 402, which do in fact exhibit a good capacity for decolorisation, possess a stability on storage, particularly on polyester substrates, which is unsatisfactory under normal conditions of storage. Normal storage in this respect is to be understood as storage with the exclusion of light and in atmospheric conditions corresponding to room temperature (i.e. in the region of 15 to 30° C.). An appreciable decrease in green-sensitivity can be observed in the course of storage.
Unsatisfactory stability of the latent image often occurs. This is manifested by a change in the sensitometric properties of the materials during storage after exposure compared with a material which is developed directly after exposure. Thus, for example, changes occur in speed, in contrast, in colour match and in colour reproduction. Since for photographic film recording materials there is generally an interval from several days to several weeks between the exposure of the material and the development thereof, good latent image stability is important for these materials.
The underlying object of the present invention is to provide a colour photographic recording material which contains a readily decolorisable yellow filter layer and which exhibits improved stability on storage. The object in particular is to improve the stability on storage of polyester-based materials. At the same time, the object is to achieve good blue-green colour separation.
Surprisingly, it has been found that an improved stability on storage can be achieved with yellow filter dyes which are known from the prior art, particularly those which are known from DE 196 46 402, by adding a compound of formula (I) to at least one layer between the substrate and the light-sensitive layer which is situated nearest to the substrate. It has thereby proved possible to achieve a sensitivity to green which is stable during normal storage. It has proved possible at the same time to achieve an improvement in latent image stability.
The present invention relates to a colour photographic recording material which contains, on a film base, at least one red-sensitive silver halide emulsion layer comprising a cyan coupler, at least one green-sensitive silver halide emulsion layer comprising a magenta coupler, at least one blue-sensitive silver halide emulsion layer comprising a yellow coupler, and at least one yellow coloured, light-insensitive layer (yellow filter layer) which is disposed below a blue-sensitive silver halide emulsion layer and above a green-sensitive silver halide emulsion layer, characterised in that the material contains, in at least one layer between the substrate and the light-sensitive emulsion layer situated nearest to the substrate, a compound of formula (I)
wherein
X and Y, independently of each other in each case, represent an electron-attracting group, and X and Y together can form a group which is necessary for the completion of a 5- or 6-membered ring.
Said compounds are preferably open-chain or (hetero)cyclic ketomethylene compounds of general formula (Ia) or of the corresponding tautomeric formula (Ib)
wherein
Y represents an electron-attracting group and
R represents alkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino or together with Y represents a group for the completion of a 5- or 6-membered ring (hetero)cycle.
The compound of formula (I) is used in an amount from 0.01 to 10 mmole/m
2
, preferably from 0.1 to 2 mmole/m
2
. In the sense of the present Application, either one compound only can be used, or a mixture of different compounds of formula (I) can be used.
The compounds according to the invention and the synthesis thereof are known from the literature.
Examples of electron-attracting groups in the sense of the present invention include R′CO—, R′R″NCO—, NC—, R′SO
2
—, R′OCO— and R′R″NSO
2
. In one preferred embodiment corresponding to formula (Ia) (formula (Ia) is also to be understood hereinafter as comprising the tautomeric form corresponding to formula (Ib)), X represents —RCO and Y represents an electron-attracting group. R′ and R″, independently of each other, can represent the radicals cited above for R. Other groups which are preferred in the sense of the present Application are described by March, in Advanced Organic Chemistry, 3rd Ed., page 17 and page 238.
In another preferred embodiment, R and Y according to formulae Ia or Ib together form a group for the completion of a 5 or 6-membered ring. Said ring can be either a heterocycle or a ring without hetero atoms. Pyrazolone, isoxazolone and pyrazolidine dione are examples of rings which are preferably formed.
Alkyl in the sense of the present Application is to be understood to mean linear or branched, cyclic or straight chain, substituted or unsubstituted hydrocarbon radicals, and in particular comprises alkyl groups containing 1 to 12 C atoms, such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, neopentyl and 2-ethylhexyl groups. These can be further substituted, however, most preferably with a carboxycarbonyl group.
Aryl in the sens
Hubner Dirk
Langen Hans
Schumann Hans-Joachim
Schutz Heinz
Sinzger Klaus
AGFA-GEVAERT
Connolly Bove & Lodge & Hutz LLP
Schilling Richard L.
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