Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2001-04-27
2002-09-24
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S556000
Reexamination Certificate
active
06455241
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith a certain imidazolonoylacetanilide type coupler having improved coupling activity and that forms a yellow dye that exhibits an improved combination of hue and stability.
BACKGROUND OF THE INVENTION
Conventional color photographic images are formed via a chromogenic development process. After exposure of a color photographic element, the object scene is stored as a composite of red, green and blue silver halide latent images. During the color development process, these silver halide latent images are reductively developed, an oxidation product of this development reacts with cyan, magenta or yellow dye-forming couplers. The composite dye image is then formed by the superpositioning of the cyan, magenta and yellow dye images to afford a reproduction of the original scene. The controlled conversion of silver halide latent image to color dye image is the goal of color photographic chemistry. The yield of dye color density from each unit of silver halide developed is a measure of coupler activity. Clearly, the higher the activity of a coupler the less silver halide is needed to allow effective image formation. The reduction in the amount of silver halide used in a photographic systems can lead to improved photographic image reproduction, lower cost photographic products, and less potential environmental concerns from development processes. Coupler or dye-forming activity, as defined herein, is composed of two prime factors: (1) the efficiency of the dye formation process, i.e., the chemistry converting coupler to dye, and (2) the light absorption properties of the chromogenically formed dye, i.e., the dye's spectral bandshape and extinction. Improvements in dye extinction are realized as improvements in coupler activity and may thereby lead to silver halide reductions.
Two further important features of photographic reproductions are their color fidelity and their image stabilities. To efficiently reproduce a wide gamut of hues, the dyes comprising the color image must exhibit relatively sharp cutting spectral curves. Additionally, the dye's spectral response curve must be carefully placed, i.e., have a well-positioned maximum absorption, to afford the desired color reproduction.
Color photographic images slowly degrade when stored under ambient conditions. Dyes, especially yellow dyes, of pictures held in the dark, that is, stored in albums, boxes or slide trays and not exposed to direct light, degrade primarily via hydrolytic mechanisms. These image dyes, when exposed to light, fade both via the hydrolytic mechanisms as well as via photochemical processes. The stability of a color image is clearly dependent upon the stabilities of its component dyes. It is apparent from these considerations that the hydrolytic stability of photographic dyes is of primary importance to image stability. The destruction of photographic dyes may be catalyzed by either acids or bases; dyes that are robustly stable to various hydrolytic conditions will provide more stable photographic images. The importance of the stability of azomethine yellow dyes toward acid catalyzed hydrolysis has been noted.
New classes of photographic yellow couplers were recently disclosed by Welter and Reynolds in U.S. Pat. Nos. 6,057,087 and 6,083,677. These patents describe new classes of azoloylacetanilide photographic couplers that provide dyes with improved spectral characteristics and stabilities. Conventional yellow dye-forming couplers include the common pivaloylacetanilide coupler class and related dyes.
It has now been found that certain new imidazolonoylacetanilide type yellow couplers can afford yellow azomethine dyes with high coupling activity, improved hues and enhanced hydrolytic stabilities over that provided by acylacetanilide couplers known heretofore.
SUMMARY OF THE INVENTION
The invention provides a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith a coupler represented by formula F-1,
wherein:
R
1
, R
3
and R
5
are independently selected from hydrogen or a substituent group and two of them may join to form a ring;
X is hydrogen or a coupling-off group;
B is hydrogen or a substituent group;
Z is a substituent group, and n varies from 0-4.
The element exhibits improved dye-forming activity and an improved combination of dye hue and dye stability.
DETAILED DESCRIPTION OF THE INVENTION
The invention is generally as described above for formula F-1. R
1
, R
3
and R
5
are independently selected from hydrogen or a substituent group and two of them may join to form a ring. Typically, R
1
is a (cyclo)alkyl, aryl or heterocyclic group such as an alkyl e.g. a methyl, butyl, octyl, dodecyl, benzyl, or a phenyl group. R
3
and R
5
are typically independently selected hydrogen or (cyclo)alkyl, aryl or heterocyclic groups such as an alkyl group e.g. a methyl, octyl group, aryl, e.g. naphthyl, or phenyl group, or heterocyclyl e.g. furyl or pyridyl group.
X is hydrogen or a coupling-off group. While the coupling-off group may include halogen, or groups linked to the rest of the coupler by a nitrogen or oxygen atom, aryloxy and N-heterocycles such as hydantoin, oxazolidinedione, or succinimido groups are conveniently employed with phenoxy being desirable.
B is hydrogen or a substituent group such as one constituting a Lewis base. A Lewis base is any compound substituent bearing a lone pair of electrons for sharing such as an alkoxy group, e.g. isopropoxy, or a halogen, e.g. chloro.
Z is a substituent group, and n varies from 0-4. These substituent groups, in toto, typically provide a net positive Hammett's sigma para sum when B is an alkoxy or other electron donating group having a negative or neutral Hammett's sigma para value group. Values of the Hammett's sigma para constant may be found, for example, in C. Hansch and A. J. Leo
Substituents for Correlation and Analysis in Chemistry and Biology
Wiley, New York (1979). When B is a halogen, there is less need for a substituent Z, especially one having a positive Hammett's sigma para value sum, from a hue standpoint. Typically, n is 0-2. Substitutions at the 3-, 4-, and/or 5-positions are most useful in many instances. Examples of suitable Z substituents include sulfone, carboxyl, carbamoyl, sulfonamido, sulfamoyl, and cyano groups.
Table I describes dyes and couplers useful in the photographic elements of the invention.
TABLE I
Invention Dye (ID) and Invention Coupler (IC) Examples.
ID-1
ID-2
ID-3
ID-4
ID-5
ID-6
ID-7
IC-1
IC-2
IC-3
IC-4
IC-5
IC-6
IC-7
IC-8
IC-9
IC-10
IC-11
IC-12
IC-13
IC-14
IC-15
IC-16
IC-17
IC-18
IC-19
IC-20
IC-21
IC-22
IC-23
IC-24
IC-25
IC-26
IC-27
Unless otherwise specifically stated, use of the term “substituted” or “substituent” means any group or atom other than hydrogen. Additionally, when the term “group” is used, it means that when a substituent group contains a substitutable hydrogen, it is also intended to encompass not only the substituent's unsubstituted form, but also its form further substituted with any substituent group or groups as herein mentioned, so long as the substituent does not destroy properties necessary for photographic utility. Suitably, a substituent group may be halogen or may be bonded to the remainder of the molecule by an atom of carbon, silicon, oxygen, nitrogen, phosphorous, or sulfur. The substituent may be, for example, halogen, such as chlorine, bromine or fluorine; nitro; hydroxyl; cyano; carboxyl, or groups which may be further substituted, such as alkyl, including straight or branched chain or cyclic alkyl, such as methyl, trifluoromethyl, ethyl, t-butyl, 3-(2,4-di-t-pentylphenoxy) propyl, and tetradecyl; alkenyl, such as ethylene, 2-butene; alkoxy, such as methoxy, ethoxy, propoxy, butoxy, 2-methoxyetho
Coms Frank D.
Welter Thomas R.
Eastman Kodak Company
Kluegel Aurthur E.
Letscher Geraldine
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