Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
1999-08-30
2001-04-17
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S505000, C430S555000, C430S506000, C430S557000, C430S957000, C430S549000
Reexamination Certificate
active
06218097
ABSTRACT:
This invention relates to a colour photographic silver halide material which is distinguished by improved processing stability.
It is known that processing stability, especially in the event of pH fluctuations in the developer, is dependent upon the nature of the colour coupler used. In the case of magenta couplers, pyrazolone couplers are, for example, distinctly better than pyrazolotriazole couplers. Nonetheless, the image quality of the negative is still excessively dependent upon the composition of the developer; negatives are produced which give rise to images having a colour cast, or, more seriously, to images suffering from colour failure. Images suffering from colour failure cannot be corrected by filtering during the printing process, i.e. the photograph is irreparably damaged. Anilinopyrazolone magenta couplers are good colour couplers with regard to colour reproduction and colour saturation.
The object of the invention was to provide a colour photographic silver halide material having improved processing stability using anilinopyrazolone magenta couplers.
This object is achieved by the combined use of anilinopyrazolone magenta couplers of the formula (I) and DIR couplers of the formula (II).
The present invention accordingly provides a colour photographic silver halide material having a support and at least one photosensitive silver halide emulsion layer which contains a magenta coupler of the formula (I)
in which
X means —N(R
5
)SR
4
, —N(R
5
)SOR
4
, —N(R
5
)SO
2
R
4
or —NHCOR
4
R
1
means halogen, cyanogen, —NO
2
, —CF
3
, alkyl, aryl, acyl, alkylsulfonyl, arylsulfonyl, acylamino, sulfonamido or silyl;
R
2
means halogen, cyanogen, —NO
2
, —CF
3
, alkyl, aryl, alkoxy, alkylthio, acyl, alkylsulfonyl, arylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, acylamino, sulfonamido or silyl;
R
3
means halogen, cyanogen, alkyl, aryl, acyl, alkylsulfonyl, arylsulfonyl or silyl;
R
4
, R
5
mean alkyl, aryl, acyl, acylamino or silyl;
a, b (mutually independently) mean 0 or an integer from 1 to 5 and
c means 0 or an integer from 1 to 4,
wherein at least 16 C atoms are present in the thiophenol group,
and which material contains a DIR coupler of the formula (II)
in which
R
6
means alkyl or alkoxy,
R
7
means hydrogen or a substituent;
R
8
means halogen, alkyl, aryl, alkoxy or aryloxy;
R
9
means hydrogen or a substituent;
R
10
means alkyl, alkylaryl or alkoxycarbonylalkyl and
R
11
means aryl or alkyl.
R
6
is preferably alkoxy;
R
7
and R
9
are preferably hydrogen atoms;
R
8
is preferably halogen, in particular chlorine;
R
10
is preferably alkyl or alkoxycarbonylalkyl,
R
11
is in particular phenyl.
In preferred embodiments of the invention, R
3
denotes H, R
4
denotes alkyl, aryl or acyl and R
5
denotes alkyl, aryl or acylamino.
The halogen represented by R
1
, R
2
or R
3
is fluorine, chlorine or bromine. An alkyl group represented by R
1
, R
2
, R
3
, R
4
or R
5
may contain, for example, 1-18 C atoms, be linear or branched and optionally be substituted; an alkyl group represented by R
4
contains, for example, 1-8 C atoms. An acyl group represented by one of the residues R
1
, R
2
, R
3
and R
4
or contained in an acylamino group represented by R
5
is derived, for example, from an aliphatic or aromatic carboxylic acid or from a carbonic acid semi-ester.
The residue of the formula
preferably has the meaning 2,4,6-trichlorophenyl.
The residue of the formula
preferably has the meaning
in which
R
12
means unsubstituted or substituted alkyl.
X is in particular —N(R
5
)So
2
R
4
or —NHCOR
4
.
Examples of couplers of the formula (I) are:
The couplers of the formula (I) and the production thereof are known from DE 195 25 666.
Suitable compounds of the formula (II) are of the formula
in which R
10
means an optionally substituted alkyl residue, for example
II-1: R
10
=—C
12
H
25
II-2: R
10
=—CH(CH
3
)COOC
12
H
25
II-3: R
10
=—C
14
H
29
II-4: R
10
=—C
16
H
33
.
The DIR coupler of the formula II is in particular used in a quantity of 5 to 50 &mgr;mol/m
2
, the magenta coupler of the formula I in a quantity of 50 to 300 &mgr;mol/m
2
.
Examples of colour photographic materials are colour negative films, colour reversal films, colour positive films, colour photographic paper, colour reversal photographic paper, colour-sensitive materials for the dye diffusion transfer process or the silver dye bleaching process.
The photographic materials consist of a support onto which at least one photosensitive silver halide emulsion layer is applied. Thin films and sheets are in particular suitable as supports. A review of support materials and the auxiliary layers applied to the front and reverse sides of which is given in
Research Disclosure
37254, part 1 (1995), page 285 and in
Research Disclosure
38957, part XV (1996), page,627.
The colour photographic materials conventionally contain at least one red-sensitive, one green-sensitive and one blue-sensitive silver halide emulsion layer, optionally together with interlayers and protective layers.
Depending upon the type of the photographic material, these layers may be differently arranged. This is demonstrated for the most important products:
Colour photographic films such as colour negative films and colour reversal films have on the support, in the sequence stated below, 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, magenta-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers. The layers of identical spectral sensitivity differ with regard to their photographic sensitivity, wherein the less sensitive sub-layers are generally arranged closer to the support than the more highly sensitive sub-layers.
A yellow filter layer is conventionally arranged between the green-sensitive and blue-sensitive layers which prevents blue light from reaching the underlying layers.
Possible options for different layer arrangements and the effects thereof on photographic properties are described in
J. Inf. Rec. Mats.,
1994, volume 22, pages 183-193 and in
Research Disclosure
38957, part XI (1996), page 624.
Colour photographic paper, which is usually substantially less photosensitive than a colour photographic film, conventionally has on the support, in the sequence stated below, one blue-sensitive, yellow-coupling silver halide emulsion layer, one green-sensitive, magenta-coupling silver halide emulsion layer and one red-sensitive, cyan-coupling silver halide emulsion layer; the yellow filter layer may be omitted.
The number and arrangement of the photosensitive layers may be varied in order to achieve specific results. For example, in a photographic film, all high sensitivity layers may be grouped together in one package of layers and all low sensitivity layers may be grouped together in another package of layers in order to increase sensitivity (DE-25 30 645).
The substantial constituents of the photographic emulsion layers are binder, silver halide grains and colour couplers.
Details of suitable binders may be found in
Research Disclosure
37254, part 2 (1995), page 286 and in
Research Disclosure
38957, part IIA (1996), page 598.
Details of suitable silver halide emulsions, the production, ripening, stabilisation and spectral sensitisation thereof, including suitable spectral sensitisers, may be found in
Research Disclosure
37254, part 3 (1995), page 286, in
Research Disclosure
37038, part XV (1995), page 89 and in
Research Disclosure
38957, part VA (1996), page 603.
Photographic materials with camera sensitivity conventionally contain silver bromide-iodide emulsions, which may optionally also contain small proportions of silver chloride. Photographic print materials contain either silver chloride-bromide emulsions with up to 80 mol % of AgBr or silver chloride-bromide emulsions with above 95 mol % of AgCl.
Details relating to colour couplers may be found in
Research Disclosure
37254, part 4 (1995), page 288, in
Research Disclosure
37038, part II (1995), page 80 and in
Research Disclosure
389
Bell Peter
Buscher Ralf
Rosenhahn Lothar
Wiesen Heinz
Wirowski Ralf
AGFA-GEVAERT
Connolly Bove & Lodge & Hutz LLP
Letscher Geraldine
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