Color photographic silver halide material

Details Color photographic silver halide material Color photographic silver halide material

2000-12-12

2002-05-07

Letscher, Geraldine (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Two or more radiation-sensitive layers containing other than...

C430S552000, C430S553000, C430S551000, C430S549000, C430S558000

Reexamination Certificate

active

06383728

ABSTRACT:

This invention relates to a color photographic silver halide material having a novel cyan coupler.
It is known from JP-N 59 111 645, U.S. Pat. No. 5,008,180 and U.S. Pat. No. 5,686,235 to use 2,5-diacylaminophenols having a sulfonyl group as cyan couplers. However, the color reproduction and dye stability of the dyes produced from the couplers by chromogenic processing do not meet requirements.
The object of the invention was to provide cyan couplers which are improved with regard to these properties. This object is achieved with the couplers described below.
The present invention accordingly provides a color photographic silver halide material having a support and at least one photosensitive silver halide emulsion layer which is associated with a cyan coupler of the formula (I):
in which
R
1
, R
2
mean H, alkyl, alkenyl, aryl or hetaryl,
R
3
means alkyl, alkenyl, aryl or hetaryl,
Z
1
means H or a group eliminable under the conditions of chromogenic development,
Y
1
means —COR
4
, —CO
2
R
4
, —CONR
4
R
5
, —SO
2
R
4
, —SO
2
NR
4
R
5
, —CO—CO
2
R
4
, —COCONR
4
R
5
or a group of the formula
R
4
means alkyl, alkenyl, aryl or hetaryl,
R
5
means H or R
4
,
R
6
means —N═ or —C(R
9
)═
R
7
, R
8
, R
9
mean —OR
5
, —SR
5
, —NR
4
R
5
, —R
5
or Cl and
n means 1 or 2.
Within the formula, the following groups of couplers are preferred:
(1) couplers in which n means 1 and R
1
to R
9
, Z
1
and Y
1
have the stated meaning.
(2) couplers in which n means 2, Y
1
means —CO—Y
11
and Y
11
means alkenyl or hetaryl and R
1
to R
3
and Z
1
have the stated meaning.
(3) couplers in which n means 2, Y
1
means —SO
2
R
10
, —SO
2
N(R
10
)
2
, —CO
2
R
10
, —COCO
2
—R
10
or —COCO—N(R
10
)
2
and R
10
means alkyl, aryl, alkenyl or hetaryl and
R
1
to R
3
and Z
1
have the stated meaning.
(4) couplers in which n means 2, Y
1
means a residue of the formula
 and R
1
to R
3
, R
6
to R
8
and Z
1
have the stated meaning.
(5) couplers in which n means 2, Y
1
means a residue of the formula
 wherein
R
10
means H, Cl, CN, Br, F, alkylcarbonyl, arylcarbonyl, alkylaminocarbonyl, arylaminocarbonyl, alkoxycarbonyl or aryloxycarbonyl and R
1
to R
3
and Z
1
have the stated meaning.
In the formula (I) and the compounds (1) to (4), the substituents have the following preferred meaning:
R
1
, R
2
H, alkyl, aryl,
R
3
alkyl, aryl,
Z
1
H, Cl, alkoxy, aryloxy, alkylthio, arylthio,
R
6
—N═,
R
7
, R
8
—OR
5
, —NR
4
R
5
, —Cl.
Very particularly preferably,
R
2
means H and
R
4
means alkyl or aryl.
Alkyl and alkenyl residues may be linear, branched or cyclic and in turn be substituted.
Aryl and hetaryl residues may in turn be substituted, wherein aryl is in particular phenyl.
Possible substituents for the alkyl, alkenyl, aryl or hetaryl residues are: alkyl, alkenyl, aryl, hetaryl, alkoxy, aryloxy, alkenyloxy, hydroxy, alkylthio, arylthio, halogen, cyano, acyl, acyloxy, acylamino, wherein an acyl residue may be derived from an aliphatic, olefinic or aromatic carbonic, carboxylic, carbamic, sulfonic, sulfonamido, sulfinic, phosphoric, phosphonic or phosphorous acid.
Examples of compounds according to the invention in which n=2 are:
Nr.
R
1
R
2
R
3
Y
1
Z
1
I-1 
—C
2
H
5
H
—Cl

I-2 
—C
2
H
5
H
—H

I-3 
—C
6
H
13
H
—OCH
2
CH
2
—SCH
2
COOH

I-4 
-phenyl
H
—Cl

I-5 
—CH
3
—CH
3
—C
16
H
33
—Cl

I-6 
-phenyl
H
—C
12
H
27
—SCH
2
CH
2
—COOH

I-7 
—C
2
H
5
H
—O—CH
2
—COOCH
3

I-8 
C
12
H
25
H
—Cl

I-9 
—C
3
H
7
-i
H
—Cl

I-10
—CH
3
—CH
3

I-11
—C
2
H
5
H
—Cl

I-12
-phenyl
H
—C
16
H
33
H

I-13
—C
12
H
25
H
—Cl

I-14
—C
4
H
9
H
—OCH
2
COOCH
3

I-15
—CH
3
—CH
3
—Cl

I-16
—C
2
H
5
H
—SO
2
—C
4
H
9
—Cl

I-17
—C
2
H
5
H
—CO—O—C
4
H
9
-i
—Cl

I-18
—C
3
H
7
-i
H
—OCH
2
—COOCH
3

I-19
-phenyl
H
—SO
2
—NH—C
4
H
9
-t
H

I-20
—C
6
H
13
H
H

I-21
—CH
3
—CH
3
—CO—CO—OC
2
H
5
—Cl

I-22
—C
4
H
9
H
—SO
2
—CH
3
—Cl

I-23
-phenyl
-phenyl
—C
12
H
25
—SO
2
C
4
H
9
—SCH
2
CH
2
—COOH

I-24
—C
12
H
25
H
—CO—O—C
2
H
5
—Cl

I-25
—C
2
H
5
H
Cl

I-26
—CH
3
H
Cl

I-27
—C
2
H
5
H
Cl
Examples of compounds according to the invention in which n = 2 and


are:
No.
R
1
R
2
R
3
R
7
R
8
R
6
Z
1
I-28
—C
2
H
5
H
—N(C
4
H
9
)
2
—N(C
4
H
9
)
2
—N═
—C—

I-29
—C
2
H
5
H
—N═
—Cl

I-30
—C
2
H
5
H
—OCH
3
—OCH
3
—N═
—Cl

I-31
—C
6
H
13
H
—Cl
—NH—C
4
H
9
—C(NHC
4
H
9
)═
H

I-32
-phenyl
H
—C
12
H
25
—OCH
3
—N(C
4
H
9
)
2
—N═
—OCH
2
COOCH
3

I-33
—CH
3
—CH
3
—NH—C
4
H
9
—NH—C
4
H
9
—C(N(C
2
H
5
)
2
)═
—Cl

I-34
H
H
—OCH
3
—NH—C
4
H
9
—N═
—S—CH
2
CH
2
—COOH

I-35
—CH
3
H
—Cl
—N═
—Cl
Compounds according to the invention in which n = 1 are:
No.
R
1
R
2
R
3
Y
1
Z
1
I-36
—C
2
H
5
H
—Cl

I-37
—C
4
H
9
H
—CO—C
3
H
7
—Cl

I-38
—C
6
H
13
H
—OCH
2
CH
2
—S—CH
2
COOH

I-39
—CH
3
—CH
3
H

I-40
-phenyl
H
—Cl

I-41
—C
2
H
5
H
H

I-42
—C
12
H
25
H

I-43
—C
4
H
9
H
—C
12
H
25
—Cl

I-44
—C
2
H
5
H
—SO
2
—C
4
H
9
—Cl

I-45
—C
3
H
7
-i
H
—C
16
H
33
—O—CH
2
—COO—CH
3

I-46
—CH
2
CH
2
CH
2
CH
2
—
—Cl

I-47
—C
2
H
5
—C
2
H
5
—CO—O—C
4
H
9
-i
H

I-48
-phenyl
H
—C
12
H
25
—CO—CO—N(C
4
H
9
)
2

I-49
—C
12
H
25
H
—CO—CH═CH—CO—N(C
2
H
5
)
2
—Cl

I-50
—C
2
H
5
H
—Cl

I-51
—C
6
H
13
H
H

I-52
—C
4
H
9
H
—Cl

I-53
—CH
3
H
—Cl

I-54
-phenyl
H
H

I-55
—C
2
H
5
H
—Cl

I-56
—C
2
H
5
H
Cl

I-57
—C
3
H
7
H
Cl

I-58
—C
2
H
5
H
H

I-59
—H
H
Cl

I-60
—C
2
H
5
H
Cl
The compounds according to the invention are produced in an analogous manner to the method stated in U.S. Pat. No. 5,686,235.
The compounds of the formula (I) are preferably used in a quantity of 5 to 2000 mg/m
2
, in particular of 10 to 1000 mg/m
2
and very particularly preferably in a quantity of 20 to 500 mg/m
2
of the material.
Examples of color photographic materials are color negative films, color reversal films, color positive films, color photographic paper, color reversal photographic paper, color-sensitive materials for the dye diffusion transfer process or the silver dye bleaching process. A review may be found in Research Disclosure 37038 (1995) and Research Disclosure 38957 (1996).
The photographic materials consist of a support, onto which at least one photosensitive silver halide emulsion layer is applied. Suitable supports are in particular thin films and sheets. A review of support materials and auxiliary layers applied to the front and reverse sides thereof is given in Research Disclosure 37254, part 1 (1995), page 285 and in Research Disclosure 38957, part XV (1996), page 627.
The color photographic materials conventionally contain at least one red-sensitive, one green-sensitive and one blue-sensitive silver halide emulsion layer, optionally together with interlayers and protective layers.
Depending upon the type of photographic material, these layers may be differently arranged. This is demonstrated for the most important products:
Colour photographic films such as color negative films and color reversal films have on the support, in the stated sequence, 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, magenta-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers. The layers of identical spectral sensitivity differ with regard to their photographic sensitivity, wherein the less sensitive sublayers are generally arranged closer to the support than the more highly sensitive sublayers.
A yellow filter layer is conventionally located between the green-sensitive and blue-sensitive layers which prevents blue light from penetrating into the underlying layers.
Possible options for different layer arrangements and the effects thereof on photographic properties are described in J. Inf. Rec. Mats., 1994, volume 22, pages 183-193 and in Research Disclosure 38957, part XI (1996), page 624.
Colour photographic paper, which is usually substantially less photosensitive than a color photographic film, conventionally has on the support, in the stated sequence, one blue-sensitive, yellow-coupling silver halide emulsion layer, one green-sensiti

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