Color photographic silver halide material

Details Color photographic silver halide material Color photographic silver halide material

2001-03-12

2003-03-11

Baxter, Janet (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Color imaging process

Color correcting

C430S505000, C430S552000, C430S553000, C430S555000, C430S557000, C430S558000

Reexamination Certificate

active

06531269

ABSTRACT:

This invention relates to a colour photographic silver halide material which has a support and at least one light-sensitive silver halide emulsion layer, and which contains a new type of masking coupler.
In colour photographic negative films, the colour saturation and colour reproduction are adjusted to the desired values by the interaction between DIR couplers and masking couplers in the individual layers.
A typical colour negative film contains at least one blue-sensitive, yellow-coupling silver halide emulsion layer next to the light source, and contains at least one green-sensitive, magenta-coupling silver halide emulsion layer and at least one red-sensitive, cyan-coupling silver halide emulsion layer which are further from the light source than is the at least one blue-sensitive layer.
Due to this arrangement, the only masking couplers which are known are those which couple from yellow to magenta and which are situated in a green-sensitive layer, and those which couple from yellow to cyan or from magenta to cyan and which are situated in a red-sensitive layer.
Cyan masking couplers, irrespective of the colour to which they couple, are not used for light-sensitive layers disposed underneath them, due to the filter effect and losses of sensitivity which are associated with them.
Surprisingly, it has now been found that even masking couplers which exhibit a coupling effect to cyan, magenta, yellow, red or to colourless substances can be used without losses of sensitivity if certain conditions of compatibility are complied with.
Thus, compared with the use of DIR couplers, colour reproduction and colour saturation can also be improved in the yellow and/or magenta layers without loss of sensitivity.
The present invention therefore relates to a colour photographic silver halide recording material of the type cited at the outset, which contains at least one cyan masking coupler which has its maximum absorption above 650 mn, wherein the red-sensitive layers have their maximum sensitivity at 620±20 mn and wherein the absorption of the masking coupler at the maximum sensitivity of the red-sensitive layers is at most 70% of its absorption at 690 nm.
The maximum absorption of the cyan masking coupler preferably corresponds to the spectral sensitivity to red of a readout sensor which has a functional relationship to the silver halide recording material, wherein a colour photographic paper or a scanner can function as a readout sensor, for example.
In the sense of the present invention, the expression “functional relationship” means that an image recorded by the material according to the invention is read out by the readout sensor, for example by an analogous exposure through the colour negative which is obtained from the material according to the invention on to the colour paper which is the readout sensor, or by reading the image information of the colour negative by means of a semiconductor sensor, e.g. by means of a CCD as a readout sensor.
In particular, the masking coupler corresponds to formula (I)
Kup-Link-Farb  (I)
wherein
Kup denotes the residue of a colour coupler,
Link denotes a linking group, and
Farb denotes the residue of a cyan dye.
Under conditions of chromogenic processing, the colour couplers can give rise in particular to colourless, magenta, yellow or red compounds, or to compounds which can be washed out in the processing method used.
For magenta-coupling masking couplers, Kup-Link preferably corresponds to formulae (II) and (III):
wherein
R
1
denotes an unsubstituted phenyl or a phenyl which is singly- or multiply-substituted by a halogen, alkyl, cyano, alkoxy, alkoxycarbonyl or acylamino,
R
2
denotes alkylamino, arylamino, acylamino or carbamoylamino,
R
3
denotes a hydrogen atom or a substituent, and
Q denotes the non-metallic atoms for the completion of a 5-membered azole ring which contains 2 to 4 nitrogen atoms and which can be substituted.
R
1
preferably denotes a phenyl group which is substituted by one or more halogen atoms, particularly 2,4,6-trichlorophenyl, 2,5-dichlorophenyl or 2-chlorophenyl, and R
2
preferably denotes arylamino or acylamino.
In particular, the couplers of formula (III) comprise pyrazolo[1,5-b]-[1,2,4]triazoles or pyrazolo[5,1-c]-[1,2,4]triazoles.
For yellow-coupling masking couplers, Kup-Link preferably corresponds to formula (IV):
wherein
R
4
and R
5
independently denote electron acceptor groups, such as acyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, cyano, nitro, sulphamoyl, alkylsulphonyl, arylsulphonyl, aryl, or heterocyclic groups which can be joined to form a ring,
R
4
preferably denotes CONHR
41
, wherein R
41
constitutes a substituted phenyl, and
R
5
preferably denotes COR
51
, wherein R
51
constitutes tert.-butyl, 4-methoxyphenyl or 1-ethylcyclopropyl.
At least one of the R
1
and R
2
radicals in formula (II), or the R
3
radical in formula (III), or one of the R
4
and R
5
radicals in formula (IV), preferably contains a ballast group which renders the masking coupler emulsifiable in a coupler solvent and which keeps the dye which is formed during colour development sufficiently hydrophobic so that it remains in the coupler solvent.
If none of the aforementioned radicals contains a ballast group, but instead contains a group which imparts solubility in water, then the dye formed during development is water-soluble and is washed out, and the masking coupler acts as a colourless-coupling masking coupler.
Suitable Kup coupler residues are listed below, where the coupling site, which at the same time is the bonding site to Link, is denoted by “Link”.
Link can be a single chemical bond or a bridging member which is bonded to the coupling position of Kup via a sulphur, nitrogen or oxygen atom. Link can contain one or more time control groups, which means that after the cleavage of the bond between Kup and Link in the course of chromogenic development the Link-Farb radical decomposes into one or more fragments after a chronological delay. If Kup does not contain a ballast radical, Link should contain a ballast radical in order to make the masking coupler resistant to diffusion.
Examples of Link groups are listed below. Kup and Farb are also given, in order to unambiguously determine the position of Link.
Farb is a chromophore, the extinction coefficient of which at 690 nm is preferably at least 30% higher than it is at 620 nm. In particular, Farb is an azomethine dye comprising one of the coupler residues of formulae (V) to (X), which are customary in photography, and a phenylenediamine developer component of formula (XI)
wherein
R
6
denotes H, SO
2
NR
61
R
62
, SO
3
R
61
, CO
2
R
61
, CONR
61
R
62
, NHCOR
62
, NHCONR
61
R
62
, NHSO
2
NR
61
R
62
, NHSO
2
R
61
, or hetaryl,
R
7
denotes a substituent,
R
8
, R
9
, R
10
, R
61
, R
62
, independently of each other, denote H or a substituent, wherein R
8
and R
9
or R
61
and R
62
can be linked to form a ring,
m denotes 0-2,
n denotes 0-4,
wherein
R
11
denotes a substituent, particularly alkyl, alkoxy or acylamino,
R
12
, R
13
denote alkyl, aryl or hetaryl, or
R
11
and R
12
together or R
12
and R
13
together denote the remaining members of a ring, particularly of a 5- or 6-membered ring,
o denotes a number from 0 to 4, and
Farb is linked to Link by one of the substituents R
6
to R
13
and one of the R
6
to R
13
radicals, or the Link radical, provided that it remains linked to Farb after chromogenic processing, contains at least one group which imparts water-solubility, for example a sulphonic acid, a sulphonamide, a carboxylic acid, a carbonamide, a hydroxy group, a polyether, an amino group or an acid group which contains phosphorus, in order to wash out the Farb or Farb-Link fragment.
Sulphonic acid and carboxylic acid groups are preferred. R
6
to R
13
are not ballasted.
Examples of Farb are listed below.
Examples of Kup-Link
Examples of Link
Examples of Farb
Other preferred embodiments of the invention are given in the subsidiary claims. In particular, all the blue-sensitive layers are dispose

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