Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2000-12-22
2001-12-11
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S556000, C430S543000
Reexamination Certificate
active
06329130
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to a silver halide photographic element containing an acylacetanilide yellow dye-forming coupler having an anilide ring bearing an ortho oxy group and a certain para ester group.
BACKGROUND OF THE INVENTION
Color silver halide photographic elements are well-known in the art. They typically include one or more light-sensitive silver halide emulsion layers sensitive to blue light that contain a yellow dye-forming coupler capable of producing a yellow image dye upon development. Most common among the suitable yellow dye-forming couplers are those based on acylacetanilide compounds. Typically the compounds are pivaloyl acetanilides.
U.S. Pat. No. 5,667,114 of Lussier et al., discloses a certain pivaloyl acetanilide coupler that contains a particular phenoxy group in the anilide ballast and provides desirable dye stability. U.S. Pat. No. 6,071,683 of Goddard et al., discloses a certain pivaloyl acetanilide coupler that contains a particular oxy group on the anilide ring of the ballast and provides desirable dye light stability.
While such compounds have been useful for providing yellow dye of the desirable density and hue needed for color imaging, further improvements in the photographic properties are needed.
It is a problem to be solved to provide a photographic element that provides a yellow dye-forming coupler that has an improved combination of reactivity and dye stability.
SUMMARY OF THE INVENTION
The invention provides a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith a yellow dye-forming coupler having formula I:
wherein
each A is independently a divalent group selected from the divalent groups consisting of aryl and —C(R
1
)(R
2
)—, in which each R
1
and R
2
is independently selected from the group consisting of hydrogen, alkyl, alkoxy, aryloxy, heterocyclic, and aryl groups, and one A can be joined to form a ring with another A or with R
3
, and m is from 2 to 6;
R
3
is selected from the group consisting of hydrogen, alkyl, heterocyclic, and aryl groups, provided that R
3
may form a ring with A or is a group joined to R
4
to form a heterocyclic five- or six-membered ring;
R
4
is selected from the group consisting of aryl, heterocyclic, and alkyl groups and may form a heterocyclic ring bonded to R
3
;
R
5
is an aryl or alkyl group;
each R
6
is an independently selected substituent and n is 0 to 3, provided that two R
6
groups may join to from a ring;
R
7
is selected from a group consisting of alkyl, aryl, heterocyclic, alkoxy, and amino groups;
Y is selected from the group consisting of —SO
2
—, —C(═O)—, —C(═O)NR
9
R
10
—, —C(═O)O—, and —P(═O)(OR
9
)(OR
10
—) where R
9
and R
10
are independently H or an alkyl or aryl group; and
Z is hydrogen or a coupling-off group.
The invention also provides a coupler compound and a method of forming an image in the photographic element of the invention.
Photographic elements of the invention provide an improved combination of speed, reactivity, and dye stability.
DETAILED DESCRIPTION OF THE INVENTION
The invention is generally as described above. In formula I, each A is independently a divalent group selected from the group consisting of aryl, and —C(R
1
)(R
2
)—, in which each R
1
and R
2
is independently selected from the group consisting of hydrogen, alkyl, alkoxy, aryloxy, heterocyclic, and aryl groups, and one A can be joined to form a ring with another A or with R
3
, and m is from 2 to 6. Desirably, the divalent group has the formula —C(R
1
)(R
2
)—. Particularly useful are such groups where m is 2. Among the groups desirable as R
1
or R
2
are hydrogen, alkyl, alkoxy methylene and aryloxy methylene groups.
In formula I, R
3
is selected from the group consisting of hydrogen, alkyl, heterocyclic, and aryl groups, provided that R
3
may form a ring with A or is a group joined to R
4
to form a heterocyclic five- or six-membered ring. R
4
is selected from the group consisting of aryl, heterocyclic, and alkyl groups and may form a heterocyclic ring bonded to R
3
. Usually, R
3
and R
4
contain the necessary carbon atoms to ballast the compound in an organic solvent.
When an R
1
or R
2
substituent represents a phenoxy containing group, it is desirable that R
4
is an alkyl group of 1-3 carbon atoms. Additionally, selection of substituents providing the desired ballasting but having lower molecular weights is preferred from a cost and materials efficiency standpoint.
In formula I, R
5
is an aryl or alkyl group. Most suitably, it is a lower alkyl group of 1-4 carbons. Particularly useful are methyl, ethyl, and isopropyl groups. Each R
6
is a substituent group provided that two R
6
groups may join to from a ring. Suitably, the group is independently selected from the group consisting of halogen, amino, and alkyl groups, and groups connected to the ring by oxygen or sulfur. “n” is 0 to 3.
R
7
is selected from a group consisting of alkyl, aryl, heterocyclic, alkoxy, and amino groups. Conveniently used are phenyl, t-butyl, methylcyclopropyl, arylamines and nitrogen heterocycles.
In formula I, Y is selected from the group consisting of —SO
2
—, —C(═O)—, —C(═O)NR
9
R
10
—, —C(═O)O—, and —P(═O)(OR
9
)(OR
10
—) where R
9
and R
10
are independently an alkyl or an aryl group. The groups —SO
2
—, —C(═O)— are most readily employed. Z is hydrogen, or a group capable of coupling-off when the coupler reacts with an oxidized color-developing agent. Z is suitably hydrogen or a five- or six-membered heterocyclic ring group wherein the group Z is bonded to the remainder of the coupler through a nitrogen atom in the ring. Examples include five and six membered containing one or more ring nitrogen atoms including azoles such as pyrazoles, succinimides, and hydantoin compounds. It is possible for Z to contain a timing group (e.g. phenoxy quinone methide) or other linking group (e.g. acyloxy) designed to release a Photographically Useful Group (PUG). Representative classes of such coupling-off groups include, for example, chloro, alkoxy, aryloxy, hetero-oxy, sulfonyloxy, acyloxy, acyl, heterocyclyl, sulfonamido, mercaptotetrazole, benzothiazole, mercaptopropionic acid, phosphonyloxy, arylthio, and arylazo.
The following are specific examples of couplers useful in the invention.
Y-1
Y-2
Y-3
Y-4
Y-5
Y-6
Y-7
Y-8
Y-9
Y-10
Y-11
Y-12
Y-13
Y-14
Y-15
Y-16
Y-17
Y-18
Y-19
Y-20
Y-21
Y-22
Y-23
Y-24
Y-25
Y-26
Y-27
Y-28
Y-29
Y-30
Y-31
Y-32
Y-33
Y-34
Y-35
Y-36
Y-37
Y-38
Y-39
Y-40
Y-41
Y-42
Y-43
Y-44
Y-45
Y-46
Y-47
Y-48
Y-49
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-methoxyethoxy, sec-butoxy, hexyloxy, 2-ethylhexyloxy, tetradecyloxy, 2-(2,4-di-t-pentylphenoxy)ethoxy, and 2-dodecyloxyethoxy; aryl such as phenyl, 4-t-butylphenyl, 2,4,6-trimethylphenyl, naphthyl; aryloxy, such as phenoxy, 2-methylphenoxy, alp
Burns Paul A.
Coms Frank D.
Lussier Barbara B.
Proseus Michael J.
Thomas Brian
Eastman Kodak Company
Kluegel Arthur E.
Letscher Geraldine
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