Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2001-08-21
2002-09-03
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S546000, C430S552000, C430S553000
Reexamination Certificate
active
06444417
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to conventional and to redox-amplified silver halide colour photographic materials and more particularly to such materials which contain a dye-forming coupler in combination with certain non-imaging compounds. The resulting dyes exhibit an exceptional combination of photographic properties, especially in regard to hue and stability. The application is related to UK application number 00230896.6 of even date herewith.
BACKGROUND OF THE INVENTION
In a silver halide photographic element, a colour image is formed when the element is exposed to light and then subjected to colour development, generally with a primary aromatic amine developer. Colour development results in imagewise reduction of silver halide and production of oxidized developer. Oxidized developer reacts with one or more incorporated dye-forming couplers to form an imagewise distribution of dye.
In any polychromatic chromogenic photographic material it is desirable that the dyes so formed should have certain properties. For instance the dyes should be bright in colour, absorbing light in the appropriate spectral region, with very little secondary absorption so that good colour reproducibility is obtained. The dyes that are formed by any colour coupler during processing have a tendency to fade over time as a result of exposure to light, heat, humidity and oxygen. Since the three image dyes may not fade at the same rate, an apparent change in image colour may result. It is thus paramount that the formed photographic dye images should be resistant towards fading by heat, humidity and light.
When the dye images are formed in silver halide photographic materials from the combination of oxidized developer and an incorporated coupler, certain restrictions are placed on the properties of the coupler. For instance, the coupler should produce a dye which has the aforementioned desirable properties and the efficiency of the dye-forming reaction must be high. Additionally, the coupler must be easily dispersible, must itself be resistant towards the deleterious effects of light, heat and humidity and must have a low propensity to form fog.
It is well known in the art of coupler chemistry that when a functionality is incorporated into a molecule to achieve one of the aforementioned desirable properties (such as high dye light stability), quite often one or more of the other desirable properties of the photographically formed dye (such as its hue) is affected adversely. It is very difficult to obtain a coupler which manifests all or even most of the aforementioned desirable properties. For example, dyes formed by diacylaminophenolic cyan couplers, whilst exhibiting excellent resistance to fading by heat and humidity, are especially deficient in their ability to withstand the effects of light and their absorption bands tend to lie at shorter wavelengths than is desirable, particularly for colour paper applications.
It is also known that the dye forming efficiency of such couplers and the stability and absorption characteristics of their image dyes can be manipulated by incorporating certain functionalities into the molecular structure of the parent coupler. For example, JP 59074556 teaches that the use of 2,5-diacylaminophenolic couplers in which the 2-benzamido group is substituted with at least one ortho-fluorine atom gives cyan couplers of high coupling efficiency (&ggr;, D
max
) in addition to good image stability of derived image dyes. In a similar manner, DE 3329729 teaches that the use of a pentafluorobenzamide substituent at the 2-position of the coupler leads to desirable bathochromic hue shifts in their image dyes. In addition it is also well known that the chemical environment in which the image dye is situated can also influence the hue of the dye. Thus, JP 59102234 teaches that certain phenolic coupler solvents tend to shift the dye absorption band derived from the fluorobenzamide-substituted couplers mentioned above to longer wavelengths.
The use of certain phosphorus blocked bis-phenol phosphate esters o improve the thermal and light stability of cyan image dyes from 2,5-diacyl-minophenolic couplers has been described in EP-A-0 913 729. Couplers in which the 2-benzamide group is substituted with fluorine atoms are disclosed in this document, but there is there is nothing to indicate that any of such couplers disclosed therein provide particular advantages over non-fluorinated couplers in image dye light stability, nor that light stability is affected by the position of the s fluorine substituent.
PROBLEM TO BE SOLVED BY THE INVENTION
There is still a need to provide a photographic element comprising a cyan dye-forming formulation which can provide an image dye of good hue and further improved light stability without significant degradation of other photographic properties.
SUMMARY OF THE INVENTION
In accordance with the embodiment of the invention there is provided a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith (A) a cyan dye-forming coupler of formula (I) and (B) a bisphenol derivative compound of formula (II):
wherein
each R
1
is a substituent provided that at least one of these is a fluoro or a perfluoroalkyl substituent;
n is an integer from 1 to 3;
R
2
is an unsubstituted or substituted alkyl, aryl, amino or alkoxy 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, and
COG is a hydrogen atom or a group which can be split off by the reaction of the coupler with an oxidized colour developing agent.
provided that
(a) when n is 3 and each R
1
is fluorine, COG is not a methoxy group and
(b) when n is 2 and R
1
in the 3- and 4-positions is each a fluorine atom, COG is not hydrogen;
wherein
R
3
is an unsubstituted or substituted alkyl, aryl, alkoxy, aryloxy group or a substituted amino group;
each Z independently represents the atoms necessary to complete a substituted or unsubstituted arene or heteroaromatic ring system;
X is a single bond or a linking group having a single atom which connects the arene or heteroaromatic ring systems; or
X forms, together with substituents ortho to X on the arene or heteroaromatic ring systems, a fused unsubstituted or substituted 5-, 6- or 7-membered ring, which may contain one or two heteroatoms selected from nitrogen, oxygen and sulfur.
In another embodiment of the invention there is provided a multi-colour 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 is 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.
ADVANTAGEOUS EFFECT OF THE INVENTION
The element of the invention provides an image dye of good hue, exhibiting exceptional stability against the effects of light, without significant degradation of other photographic properties.
DETAILED DESCRIPTION OF THE INVENTION
The combination of the invention is generally as described in the Summary of the Invention. The combination comprises the compounds (I) and
Cyan Dye-Forming Coupler (I)
The cyan dye-forming coupler has the formula (I):
wherein
each R
1
is a substituent provided that at least one of these is a fluoro or a perfluoroalkyl substituent;
n is an integer from 1 to 3;
R
2
is an unsubstituted or substituted alkyl, aryl, amino or alkoxy 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; and
COG is a hydrogen atom or a group which can be split off by the reaction of the coupler wi
Clarke David
Leyshon Llewellyn J.
Smith Katie E.
Eastman Kodak Company
Kluegel Arthur E.
Letscher Geraldine
LandOfFree
Photographic element containing cyan dye-forming coupler does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photographic element containing cyan dye-forming coupler, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photographic element containing cyan dye-forming coupler will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2881706