Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
1999-09-21
2001-01-16
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S549000, C430S555000, C430S558000, C430S957000
Reexamination Certificate
active
06174662
ABSTRACT:
BACKGROUND OF THE INVENTION
Many photographic materials, particularly color negative films, contain so-called DIR (development inhibitor releasing) couplers. In addition to forming imaging dye, DIR couplers release inhibitors that can restrain silver development in the layer in which release occurs as well as in other layers of a multilayer photographic material. DIR couplers can help control gamma (contrast), can enhance sharpness (acutance), can reduce granularity and can provide color correction via interlayer interimage effects. U.S. Pat. No. 3,933,500 broadly discloses couplers with azole coupling-off groups. Specifically coupler 13 of U.S. Pat. No. 3,933,500 discloses a pyrazolone parent coupler with a simple purine coupling-off group. Purine-releasing pyrazolone DIR couplers are also disclosed in commonly assigned, copending U.S. patent applications Ser. Nos. 08/824,226 and 08/824,223 both filed Mar. 25, 1997.
PROBLEM TO BE SOLVED BY THE INVENTION
There has been a need for more effective magenta dye-forming DIR couplers. Magenta DIR couplers that provide high interimage color correction are particularly desirable for modem color negative films. To efficiently react with oxidized developer and provide inhibition effects, a magenta dye-forming DIR coupler must have a reactivity that is properly matched with that of the magenta imaging coupler that is coated with it and must release an inhibitor that efficiently retards silver development. Since a DIR coupler is normally coated at lower levels than the imaging coupler, the reactivity of the DIR must usually be high to compete for reaction with oxidized developer.
SUMMARY OF THE INVENTION
This invention provides a combination of a pyrazolone DIR coupler and pyrazolone or pyrazolotriazole image coupler. A photographic element containing these couplers possess all of the above-mentioned desirable properties, particularly the ability to provide higher interimage color correction than combinations of the prior art, such as those disclosed in the above-mentioned U.S. Pat. No. 3,933,500 and copending U.S. patent applications Ser. Nos. 08/824,226 and 08/824,223. The DIR couplers used in accordance with this invention are 1-aryl-3-anilino-5-pyrazolones that release a purine derivative from the coupling position (4-position).
One aspect of this invention comprises a photographic element comprising (a) a support; and (b) at least one silver halide emulsion layer; wherein said emulsion layer contains (c) at least one magenta dye-forming pyrazolone DIR coupler of structure I; and (d) at least one magenta dye-forming imaging coupler of structure II, structure IIIa or structure IIIb, below:
wherein:
Ar
1
is an unsubstituted aryl group or an aryl group with one or more substituents selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, sulfonamido, carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkylsulfonyl, arylsulfonyl, sulfonyloxy and alkylthio groups;
R
1
is a hydrogen or halogen atom or an alkyl or alkoxy group;
each R
2
is individually selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, sulfonamido, carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, alkylthio, arylthio, cyano and imido groups and is in the para position or either meta position relative to the NH group;
m is 0, 1, 2 or 3;
R
3
is an alkylthio, arylthio, alkoxy, phenoxy, sulfonamido or carbonamido (—NHCOR
4
) group; and
R
4
is an alkyl, phenyl, alkoxy or phenoxy group;
wherein:
Ar
2
is an unsubstituted aryl group or an aryl group with one or more substituents individually selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, alkylthio and cyano groups;
R
6
is a hydrogen or halogen atom or an alkyl or alkoxy group;
each R
7
may be in the para position or either meta position relative to the NH group and is individually selected from the group consisting of halogen atoms and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, cyano, imido, alkylthio and arylthio groups;
q is, 0, 1, 2 or 3;
R
8
and R
9
are individually selected from the group consisting of hydrogen and halogen atoms and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy and cyano groups;
r is 0, 1 or 2;
R
9
is in the para or either meta position relative to the sulfur atom; and
the total number of carbon atoms in R
8
and R
9
taken together is at least 4;
wherein:
R
10
and R
11
are individually selected from the group consisting of hydrogen and halogen atoms and alkyl, phenyl, alkoxy, phenoxy, carbonamido and sulfonamido groups;
X is hydrogen or a coupling-off group; and
the total number of carbon atoms in R
10
and R
11
taken together is at least 8.
ADVANTAGEOUS EFFECT OF THE INVENTION
The combination of the DIR coupler of formula I and an image coupler of formula (II), (IIIa) or (IIIb) provides a photgaphic element that has the desired contrast, accutance, granularity and interimage effects.
DETAILED DESCRIPTION OF THE INVENTION
As mentioned above, the photographic element of this invention comprises (a) a support; and (b) at least one silver halide emulsion layer; wherein said emulsion layer contains (c) at least one magenta dye-forming pyrazolone DIR coupler of structure I; and (d) at least one magenta dye-forming imaging coupler of structure II, structure IIIa or structure IIIb, below:
wherein:
Ar
1
is an unsubstituted aryl group or an aryl group with one or more substituents selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, sulfonamido, carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkylsulfonyl, arylsulfonyl, sulfonyloxy and alkylthio groups;
R
1
is a hydrogen or halogen atom or an alkyl or alkoxy group;
each R
2
is individually selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, sulfonamido, carbamoyl, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, alkylthio, arylthio, cyano and imido groups and is in the para position or either meta position relative to the NH group;
m is 0, 1, 2 or 3;
R
3
is an alkylthio, arylthio, alkoxy, phenoxy, sulfonamido or carbonamido (—NHCOR
4
) group; and
R
4
is an alkyl, phenyl, alkoxy or phenoxy group;
wherein:
Ar
2
is an unsubstituted aryl group or an aryl group with one or more substituents individually selected from the group consisting of halogen atoms, and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, alkylthio and cyano groups;
R
6
is a hydrogen or halogen atom or an alkyl or alkoxy group;
each R
7
may be in the para position or either meta position relative to the NH group and is individually selected from the group consisting of halogen atoms and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy, cyano, imido, alkylthio and arylthio groups;
q is 0, 1, 2 or 3;
R
8
and R
9
are individually selected from the group consisting of hydrogen and halogen atoms and alkyl, phenyl, alkoxy, phenoxy, carbonamido, carbamoyl, acyloxy, alkoxycarbonyl, aryloxycarbonyl, sulfonamido, sulfamoyl, alkylsulfonyl, arylsulfonyl, sulfoxyl, sulfonyloxy and cyano groups;
r is 0, 1 or 2;
R
9
is in the para or either meta position relative to the sulfur atom; and
the total number of carbon atoms in R
8
and R
9
taken together is at least 4;
wherei
Merkel Paul B.
Poslusny Jerrold N.
Steele David A.
Eastman Kodak Company
Letscher Geraldine
Rice Edith A.
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