Radiation imagery chemistry: process – composition – or product th – Color imaging process – Using identified radiation sensitive composition in the...
Reexamination Certificate
2001-05-22
2004-03-02
Fredman, Jeffrey (Department: 1634)
Radiation imagery chemistry: process, composition, or product th
Color imaging process
Using identified radiation sensitive composition in the...
C430S385000, C430S552000, C430S553000, C430S558000, C435S006120, C427S213300, C264S004100
Reexamination Certificate
active
06699650
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a colour photographic element containing a novel phenolic cyan image dye-forming coupler and in particular a coupler containing an N-alkyl sulphonamide substituent.
BACKGROUND OF THE INVENTION
In silver halide based colour photography, a typical photographic element contains multiple layers of light-sensitive photographic silver halide emulsions coated on a support with one or more of these layers being spectrally sensitised to each of blue light, green light and red light. The blue, green and red light-sensitive layers typically contain yellow, magenta, and cyan image dye-forming couplers, respectively. After exposure to light, colour development is accomplished by immersing the exposed material in an aqueous alkali solution containing an aromatic primary amine colour developing agent. The dye-forming couplers, hereinafter image couplers, are selected so as to react with the oxidised colour developing agent to provide yellow, magenta and cyan dyes in the so called subtractive colour process to reproduce their complementary colours, blue, green and red as in the original image.
The important features for selecting the image coupler include; efficient reaction with oxidised colour developing agent, thus minimising the necessary amounts of coupler and silver halide in the photographic element; the formation of dyes with hues appropriate for the photographic use of interest: for colour photographic paper applications this requires that dyes have low unwanted side absorption leading to good colour reproduction in the photographic print; minimisation of image dye loss contributing to improved image permanence under both ambient illumination and conventional storage conditions; and in addition the selected image coupler must exhibit good solubility in coupler solvents, provide good dispersibility in gelatin and remain stable during handling and manipulation for maximum efficiency in manufacturing processes.
In recent years, a great deal of study has been conducted to improve image couplers for silver halide photosensitive materials in terms of improved colour reproducibility and image dye stability. However, further improvements are needed, particularly in the area of cyan couplers. In general, cyan dyes are formed by the reaction of, generally, phenols or naphthols with oxidised colour developing agents as described, for example, in U.S. Pat. Nos. 2,367,351, 2,423,730, 2,474,293, 2,772,161, 2,772,162, 2,895,826, 2,920,961, 3,002,836, 3,034,892, 3,041,236, 3,466,622, 3,476,563, 3,552,962, 3,758,308, 3,779,763, 3,839,044, 3,880,661, 3,998,642, 4,214,396, 4,299,914, 4,362,810, 4,333,999, 4,883,746, 4,990,436, 4,960,685, 5,476,757 and 5,614,357; in French Patent Nos. 1,478,188 and 1,479,043, in UK Patent No. 2,070,000 and “Farbkuppler—Eine Literature Ubersicht,” published in Agfa Mitteilungen, Band III, pp. 156-175 (1961). Also useful are the cyan couplers described in, for instance, European Patent Application Nos. 544,322; 556,700; 556,777; 565,096; 570,006; and 574,948 and JP-A-59069755.
These types of image couplers can be used either by being incorporated in the photographic silver halide emulsion layers or externally in the processing baths. In the former case the couplers must have ballast substituents built into the molecule to prevent the couplers from migrating from one layer into another. Although these couplers have been used extensively in colour photographic film and paper products, the dyes derived from them still suffer from poor stability to heat, humidity or light, low coupling efficiency or optical density, and in particular from undesirable blue and green absorptions which cause considerable reduction in colour reproduction and colour saturation.
2,5-diacylamino phenols are well known in the art of photography, and it is also well known that image dyes derived from them exhibit good resistance to fading by heat and humidity. However their image dyes are deficient in their ability to withstand the effects of light. Moreover, their absorption bands tend to lie at shorter wavelengths than is desirable, particularly for colour paper applications.
It is known that the absorption characteristics of image dyes can be manipulated by incorporating certain functionalities into the molecular structure and that the chemical environment in which the dye is situated can also influence the hue of the dye. For example, U.S. Pat. No. 5,376,519 and JP 5,9171,953 teach the use of certain phenolic coupler solvents to shift the dye absorption band to longer wavelengths.
PROBLEM TO BE SOLVED BY THE INVENTION
There is still a need to provide a photographic element containing a dispersion of a cyan dye-forming coupler which can provide improved light and dark stability under normal storage conditions, improved colour reproduction in the generation of photographic images and high reactivity for formation of dye with oxidised colour developing agent.
SUMMARY OF THE INVENTION
According to the present invention there is provided a photographic element comprising at least one silver halide emulsion layer having associated therewith a phenolic cyan dye-forming coupler of formula (I)
wherein
X is hydrogen or a group that can be split off by the reaction of the coupler with an oxidised colour developing agent, and
one of Y and Z is the group
wherein
each R is independently an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted;
R
1
is hydrogen of an unsubstituted or substituted alkyl or aryl group,
R
2
is an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted;
R
3
is hydrogen or an unsubstituted or substituted alkyl or aryl group,
n is 1 or 2, and each group —N(R
2
)SO
2
R is in the ortho or para position,
the other of Y and Z is a fluoro-substituted alkyl group or an unsubstituted or substituted aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfer, which ring is unsubstituted or substituted, provided that (a) when R
2
is an unsubstituted benzyl group, n is 1 and —N(R
2
)SO
2
R is in the ortho position, R may not be a pyridyl group, and (b) at least one of R, R
1
, R
2
, X and Y or Z is or includes a ballast group.
In another embodiment of the invention there is provided a multicolour photographic element comprising a support bearing yellow, magenta and cyan image-dye-forming units comprising at least one blue-, green- or red-sensitive silver halide emulsion layer having associated therewith at least one yellow, magenta or cyan dye-forming coupler respectively, wherein the element comprises at least one cyan dye-forming coupler of formula (I) as herein described.
In yet another embodiment of the invention there is provided a process of forming an image in a photographic element as hereinbefore defined after the element has been imagewise exposed to light, comprising contacting the element, as herein described, with a colour developing agent.
In a further embodiment of the invention there is provided a novel coupler of formula (I) as herein described.
ADVANTAGEOUS EFFECT OF THE INVENTION
This invention provides an element which yields a cyan image of good hue, with good stability to heat, humidity and light, whilst retaining the other properties desirable for good photographic performance.
DETAILED DESCRIPTION OF THE INVENTION
As used herein and throughtout the specification unless where specifically stated otherwise, the term “alkyl” refers to an unsaturated or saturated, straight or branched chain alkyl group, including alkenyl and aralkyl, and includes cyclic alkyl groups, including cycloalkenyl, having 3-8 carbon atoms and the term “aryl” includes specifically fused aryl. The term “low alkyl” refers to an alkyl group having up to 6 carbon a
Clarke David
Leyshon Llewellyn J.
Smith Katie E.
Fredman Jeffrey
Kluegel Arthur E.
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