Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
1998-05-14
2001-04-24
Baxter, Janet (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S558000
Reexamination Certificate
active
06221572
ABSTRACT:
This invention relates to a colour photographic material having a support and at least one light-sensitive silver halide emulsion layer and at least one colour coupler associated with this layer, which on development with a colour developer forms a dye which is distinguished by improved stability to light due to a new type of dye stabiliser which is added to the layer.
It is known that dyes which are formed on the development of a colour photographic material, particularly magenta dyes, and quite particularly those which are based on pyrazolotriazole magenta couplers, have to be stabilised against their destruction by light. Thus, for example, EP 273 412 and EP 273 712 describe aminophenol ethers with cyclic amine substituents, and EP 457 543 describes the same compounds in combination with bisphenols as stabilisers for an azomethine dye formed from pyrazolotriazole magenta couplers. The effect of these materials, even in combination with other stabilisers, is still not satisfactory.
Compounds have now been found which impart a higher stability to dyes such as these, particularly in relation to light.
The present invention therefore relates to the material cited at the outset, characterised in that in the light-sensitive layers it contains at least one compound of formula (I)
wherein
m denotes 0, 1, 2, 3 or 4,
n denotes 2, 3, 4, 5 or 6,
R
1
denotes a di- to hexavalent group,
R
2
denotes alkyl, alkenyl, cycloalkyl, aryl alkoxy, aryloxy, alkylthio, arylthio, acyl, alkoxycarbonyl, aryloxycarbonyl, hydroxy, halogen, cyano, —SO
2
R
5
, —SOR
5
, —CON(R
5
)R
6
or —SO
2
N(R
5
)R
6
,
L
1
denotes alkylene, arylene, aralkylene or alkylidene,
L
2
denotes
L
3
, L
4
denote a C
1
-C
3
alkylene which is optionally substituted,
X denotes
or
R
3
denotes H, acyl, —SO
2
R
5
, alkoxycarbonyl aryloxycarbonyl alkyl aryl, alkenyl or the radical of a heterocycle,
R
4
denotes H, alkyl, aryl or the radical of a heterocycle,
R
5
denotes alkyl or aryl, and
R
6
denotes H or R
5
, wherein
2 R
3
and R
4
radicals may be the same or different.
Preferably,
R
1
denotes a di- to hexavalent aliphatic or aromatic group,
R
2
denotes alkyl, alkoxy, acyl, alkoxycarbonyl or hydroxy,
R
3
denotes H or alkyl,
L
1
denotes alkylene, arylene or aralkylene,
L
2
X denotes —SO—, —SO
2
—, —CO— or —O—, and
m denotes 0, 1 or 2,
wherein
L
3
and L
4
together contain 3 to 5 C atoms.
The compounds of formula I preferably have a molecular weight of at least 650. They are used in particular in an amount of 5 to 1500 mg/m
2
, preferably 10 to 500 mg/m
2
of colour photographic material.
Examples of compounds according to the invention are:
a) L
3
=L
4
=—CH
2
—CH
2
—; linkage of the —O—L
1
—L
2
—R
1
group para to the nitrogen; position of R
2
given with respect to O.
In one preferred embodiment, the layer containing the magenta coupler also contains at least one compound of formula II or III in addition:
wherein
R
11
denotes H, acyl, alkoxycarbonyl, —CON(R
5
)R
6
, —SO
2
R
5
, —SO
2
N(R
5
)R
6
, aryloxy-carbonyl, alkyl or alkenyl,
R
12
denotes alkyl, aryl, aralkyl, alkenyl, halogen, alkoxy, acyloxy, aryloxy, acyl, acyl-amino, —CON(R
5
)R
6
, alkoxycarbonylamino, —N(R
6
)CON(R
5
)R
6
, alkoxycarbonyl or aryloxycarbonyl,
p, q denote 0 or a number from 1 to 4,
L
11
denotes
R
13
denotes H, alkyl, aryl, acyl, alkoxycarbonyl, —CON(R
5
)R
6
or aryloxycarbonuyl,
wherein a plurality of radicals R
12
, R
13
may be the same or different, and one substituent is situated para to the OH or OR
11
in each case,
wherein
R
21
denotes alkyl, aryl, alkoxy, aryloxy, hydroxy, acyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, —CON(R
5
)R
6
, —SO
2
R
5
, —SO
2
N(R
5
)R
6
, alkoxycarbonylamino, —N(R
6
)CON(R
5
)R
6
or acyloxy,
R
22
denotes R
21
or halogen, and
r denotes 0 or an integer from 1 to 4,
wherein a plurality of radicals R
22
may be the same or different.
The compounds of formulae (II and (III) are used in a total amount of 5 to 1500 mg/m
2
in each case, preferably 10 to 750 mg/m
2
.
Examples of compounds of formulae II and III are:
Examples of colour photographic materials include colour negative films, colour reversal films, colour positive films, colour photographic paper, colour reversal photographic paper, and colour-sensitive materials for the colour diffusion transfer process or the silver halide bleaching process.
Photographic materials consist of a support on which at least one light-sensitive silver halide emulsion layer is deposited. Thin films and foils are particularly suitable as supports. A review of support materials and of the auxiliary layers which are deposited on the front and back thereof is given in Research Disclosure 37254, Part 1 (1995), page 285 and in Research Disclosure 38957, Part XV (1996), page 627.
Colour photographic materials usually contain at least one red-sensitive, at least one green-sensitive and at least one blue-sensitive silver halide emulsion layer, and optionally contain intermediate layers and protective layers also.
Depending on the type of photographic material, these layers may be arranged differently. This will be illustrated for the most important products:
Colour photographic films such as colour negative films and colour reversal films comprise, in the following sequence on their support: 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 as regards their photographic speed, wherein the less sensitive partial layers are generally disposed nearer the support than are the more highly sensitive partial layers.
A yellow filter layer is usually provided between the green-sensitive and blue-sensitive layers, to prevent blue light from reaching the layers underneath.
The options for different layer arrangements and their effects on photographic properties are described in J. Inf Rec Mats., 1994, Vol. 22, pages 183-193, and in Research Disclosure 38957, Part Xl (1996), page 624.
Colour photographic paper, which as a rule is less sensitive to light than is colour photographic film, usually comprises the following layers on the support, in the following sequence: a blue-sensitive, yellow-coupling silver halide emulsion layer, a green-sensitive, magenta coupling silver halide emulsion layer, and a red-sensitive, cyan-coupling silver halide emulsion layer.
Departures from the number and arrangement of the light-sensitive layers may be effected in order to achieve defined results. For example, all the high-sensitivity layers may be combined to form a layer stack and all the low-sensitivity layers may be combined to form another layer stack in a photographic film, in order to increase the sensitivity (DE 25 30 645).
The essential constituents of the photographic emulsion layer are the binder, the silver halide grains and colour couplers.
Information on suitable binders is given in Research Disclosure 37254, Part 2 (1995), page 286, and in Research Disclosure 38957, Part IIa (1996), page 598.
Information on suitable silver halide emulsions, their production, ripening, stabilisation and spectral sensitisation, including suitable spectral sensitisers, is given 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 which exhibit camera-sensitivity usually contain silver bromide-iodide emulsions, which may also optionally contain small proportions of silver chloride. Photographic copier materials contain either silver chloride-bromide emulsions comprising up to 80 mole % AgBr, or silver chloride-bromide emulsions comprising more than 95 mole % AgCl.
Information on colour couplers is to be found in Research Disclosure 37254, Part 4 (1995), page 288, in Research Disclosure 37038, Part II (1995), page 80, and in Research Disclosure 38957, Part XB (1996), page 616. The maximum absorption of the dyes formed from the couplers
Hagemann Jorg
Helling Gunter
Odenwalder Heinrich
Afga-Gevaert Naamloze Vennootschap
Baxter Janet
Connolly Bove & Lodge & Hutz LLP
Walke Amanda C.
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