Color photographic silver halide material

Details Color photographic silver halide material Color photographic silver halide material

2002-01-10

2003-05-27

Le, Hoa Van (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Two or more radiation-sensitive layers containing other than...

C430S361000

Reexamination Certificate

active

06569611

ABSTRACT:

This invention relates to a color photographic silver halide material having a support and at least three differently sensitised photosensitive silver halide emulsion layers, which material contains a novel masking coupler.
In color photographic negative films, color saturation and color reproduction are adjusted to the desired value in the individual layers by the interplay between DIR couplers and masking couplers.
A typical color negative film contains closest to the light source at last one blue-sensitive, yellow-coupling silver halide emulsion layer and, further away from the light source than the at least one blue-sensitive layer, at least one green-sensitive, magenta-coupling silver halide emulsion layer and at least one red-sensitive, cyan-coupling silver halide emulsion layer.
Due to this arrangement, masking couplers are known which couple from yellow to magenta and are located in a green-sensitive layer, as are masking couplers which couple from yellow to cyan or from magenta to cyan and are located in a red-sensitive layer. Conventional masking couplers are accordingly those which couple from a dye having a short wavelength absorption maximum to a dye having a longer wavelength absorption maximum.
Reverse coupling in the opposite direction, for example from cyan to magenta is known from U.S. Pat. No. 5,466,566, but has not hitherto been implemented in practice.
Using DIR reduces the sensitivity of a color photographic material; the DIR coupler for example by the action of the inhibitor released from it, which is required to improve color purity, and both types by consumption of developer oxidation product.
The object of the invention was to avoid or at least reduce these disadvantages.
It has now surprisingly been found that this object is achieved with a masking coupler which has two chromophores which absorb in the wavelength range from 420 to 750 nm and are eliminable or decolorisable by coupling with the developer oxidation product. The chromophores may absorb at identical or very similar wavelengths or at different wavelengths.
A very similar wavelength means that the absorption maxima of the two chromophores differ by no more than 30 nm; a different wavelength means that the absorption maxima of the two chromophores differ by at least 30 nm.
The object is in particular achieved with a masking coupler which exhibits an absorption maximum in two of the three ranges of the spectrum to which the readout sensor (photographic paper, semiconductor sensor) is sensitive, i.e. both in the blue and the green range or both in the blue and the red range or both in the green and the red range.
The dye produced by coupling may have its absorption maximum in any desired absorption range.
The coupler according to the invention preferably couples to yield a dye with an absorption maximum in the remaining, third range of the spectrum.
If, for example, the masking coupler absorbs blue and red light, it preferably couples to yield magenta, the complementary color to green.
Particularly preferred masking couplers are those which absorb blue and green light and couple to cyan, and masking couplers which absorb blue and red light and couple to magenta.
The maximum absorption of the masking coupler for red light preferably corresponds to the spectral red sensitivity of a readout sensor, which is in a functional relationship with the silver halide recording material, wherein, for example, a color photo-graphic paper or a scanner may act as the readout sensor.
For the purposes of this invention, functional relationship means that a scene recorded with the material according to the invention is read out by the readout sensor, for example by an analogue exposure through the color negative obtained from the material according to the invention onto the color paper as readout sensor, or by reading out the image information of the color negative by means of a semiconductor sensor, for example by means of a CCD, as the readout sensor.
The masking coupler is in particular of the formula (I)
Kup-Farb-1-Farb-2  (I)
in which
Kup means the residue of a color coupler
Farb-1 means the residue of a first chromophore, in particular a fragment which, together with Kup, forms a dye and
Farb-2 means the residue of a second chromophore.
Under chromogenic processing conditions, the color couplers may in particular yield colorless, magenta, yellow, red or cyan compounds or compounds which can be rinsed out during processing.
Magenta-coupling masking couplers are preferably of the formulae (II) and (III):
in which
R
1
means unsubstituted phenyl or phenyl mono- or polysubstituted by halogen, alkyl, cyano, alkoxy, alkoxycarbonyl or acylamino,
R
2
means alkylamino, arylamino, acylamino or carbamoylamino
R
3
means a hydrogen atom or a substituent and
Q means the non-metallic atoms to complete a 5-membered azole ring with 2 to 4 nitrogen atoms, which ring may be substituted.
Preferably, R
1
means phenyl substituted by one or more halogen atoms, in particular 2,4,6-trichlorophenyl, 2,5-dichlorophenyl or 2-chlorophenyl, and R
2
means aryl-amino or acylamino.
The couplers of the formula (III) in particular comprise pyrazolo[1,5-b]-[1,2,4]-triazoles or pyrazolo[5,1-c]-[1,2,4]triazoles.
Cyan-coupling masking couplers are preferably of the formula (IV):
in which
R
4
bis R
7
mean hydrogen atoms or substituents. R
4
and R
5
or R
6
and R
7
may be linked together to form a ring.
A preferred formula is
in which
R
8
means a hydrogen atom or a substituent such as acylamino, sulfonylamino or alkoxycarbonylamino,
R
9
means a substituent,
n9 means a number from 0 to 3 and
R
10
and R
1
means hydrogen atoms or substituents, which may be linked together to form a ring, in particular alkyl or aryl.
Furthermore, in the formula (IV)
R
4
preferably means acylamino or carbamoylamino,
R
5
and R
6
preferably mean hydrogen atoms and
R
7
preferably means acylamino.
Yellow-coupling masking couplers are preferably of the formula (VI):
in which
R
12
, R
13
mean electron acceptor groups such as acyl, alkoxycarbonyl, aryloxy-carbonyl, carbamoyl, cyano, nitro, sulfamoyl, alkylsulfonyl, arylsulfonyl, aryl or heterocyclic groups, which may be joined together into a ring.
Preferably, R
12
means CONHR
14
, wherein R
14
represents a substituted phenyl, and R
13
means COR
15
, wherein R
15
represents tert.-butyl, 4-methoxyphenyl or 1-ethyl-cyclopropyl.
At least one of the residues R
1
and R
2
in the formula (II), one of the residues R
3
or Q in the formula (III), one of the residues R
4
to R
7
in the formula (IV) or one of the residues R
12
and R
13
in the formula (VI) preferably contains a ballast group which renders the masking coupler emulsifiable in a coupler solvent and which keeps the dye arising on color development sufficiently hydrophobic to remain in the coupler solvent.
If none of the above-stated residues contains a ballast group, but instead a water-solubilising group, the dye formed on development then becomes water-soluble, is washed out and the masking coupler acts as a masking coupler which couples to colorless.
Suitable coupler residues Kup are stated below, wherein the coupling site, simultaneously the bonding site to Farb-1, is indicated “Farb-1”.
Farb-1 may be a dye or a fragment which forms a dye with Kup, which fragment is attached to the coupling position of Kup via a sulfur, nitrogen or oxygen atom. Farb-1 may contain one or more time control members, which means that, once the bond between Kup and Farb-1 has been cleaved during chromogenic development, the residue Farb-1-Farb-2 breaks down into one or more fragments in time-delayed manner. If Kup contains a ballast residue, Farb-1 or Farb-2 should contain a ballast residue in order to render the masking coupler diffusion-resistant.
Farb-1 is preferably attached to Kup with an azo group, such that Kup-Farb-1 is a dye which absorbs in a different range of the spectrum than does the dye arising from Kup on development.
Examples of Farb-1 groups are listed below. Kup and Farb-2 are also stated i

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