Color photographic material

Details Color photographic material Color photographic material

1999-09-10

2001-06-05

Letscher, Geraldine (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Identified radiation sensitive composition with color...

C430S551000, C430S558000

Reexamination Certificate

active

06242169

ABSTRACT:

This invention relates to a colour photographic material containing an emulsified heterocyclic cyan coupler from the group of pyrazoloazoles and certain coupler solvents.
It is known to produce coloured photographic images by chromogenic development, i.e. by developing silver halide emulsion layers exposed with an image by means of suitable chromogenic developer substances, so-called colour developers, in the presence of suitable colour couplers, wherein the oxidation product of the developer substance, which oxidation product is produced congruently with the silver image, reacts with the colour coupler to form a dye image.
Naphtholic or phenolic cyan couplers are conventionally used to produce the cyan component colour image. The latter have hitherto been preferred in colour photographic print materials due to the more favourable absorption (at approx. 660 nm) and greater dark storage stability of the image dyes produced therefrom on chromogenic development.
However, in comparison with the image dyes produced from conventional pivaloylacetanilide yellow couplers and pyrazolotriazole magenta coupler, the dark storage stability is inadequate. Moreover, the phenolic cyan dyes have a relatively large half-width, which gives rise to a distinct, unwanted absorption in the green range of the spectrum.
In order to eliminate these disadvantages it has been proposed, inter alia in EP 717 315, to use specially substituted pyrazoloazoles as cyan couplers. However, in conventional coupler solvents, the dyes produced from these couplers exhibit an unwanted shift of the absorption flank towards shorter wavelengths. Excessively low light stability is another disadvantage.
The object of the present invention was to provide colour photographic materials containing pyrazoloazole cyan couplers which are distinguished by improved light stability and which simultaneously exhibit thermal stability. A further object was to provide cyan couplers having colour reproduction which is distinctly improved in comparison with known prior art materials.
The present invention provides a colour photographic material containing at least one silver halide emulsion layer sensitised for the red range of the spectrum, which layer contains associated therewith at least one compound of the formula (I)
in which
R
11
and R
12
mutually independently denote an electron-attracting group,
X
11
denotes H or a group seperable on reaction with the developer oxidation product,
Y
11
denotes a group to complete a nitrogenous heterocycle, providing that a group represented by R
12
is attached to a carbon atom of the heterocycle,
n denotes 1 or 2,
and at least one compound of the formula (II)
in which
R
21
denotes alkyl, alkenyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, acyl, acylamino, acyloxy, hetaryl, halogen, nitro or cyano,
R
22
denotes OH or has the same meaning as R
21
,
n, m mutually independently denote 0 or 1,
o denotes 0, 1, 2, 3, 4 or 5, providing that the compound contains a total of at least 16 C atoms.
For the purposes of the present application, alkyl should be taken to mean linear or branched, straight-chain or cyclic, substituted or unsubstituted hydrocarbon groups, preferably alkyl groups having 1 to 32 C atoms. Open-chain alkyl groups which may be considered are in particular methyl, ethyl, n-propyl, n-butyl, n-octyl, n-dodecyl, n-hexadecyl and n-octadecyl, while branched alkyl residues are in particular 2-hexyl-decyl, 2-octyldodecyl and 2-ethylhexyl residues. Preferred cycloalkyl groups are cyclohexyl, in particular 4-t.-butylcyclohexyl, 2,6-di-t.-butyl-4-methylcyclohexyl. For the purposes of the present application, alkenyl should be taken to mean linear or branched cyclic or straight-chain substituted or unsubstituted unsaturated hydrocarbon residues, such as for example ethenyl, 2-propenyl, isopropenyl and oleyl. For the purposes of the present application, aryl should be taken to mean aromatic hydrocarbons, wherein phenyl or naphthyl is preferred. These may be both substituted and unsubstituted. For the purposes of the present application, hetaryl should be taken to mean aromatic systems which contain at least one heteroatom. These also preferably comprise 5- or 6-membered ring systems, which may present not only as monocyclic but also as fused ring systems. The ring systems may in this case be both substituted and unsubstituted ring systems. Heteroatoms which may in particular be considered here are N, S and O. A ring system may preferably have between 1 and 3 heteroatoms, wherein the heteroatoms may be identical or different. In the case of fused ring systems, two or more identical or different heterocyclic systems may be fused, as well as hetaryls with arylene. Typical examples are: pyridine, pyridazine, pyrimidine, pyrazine, oxazole, isoxazole, thiazole, 3,4-oxadiazole, 1,2,4-oxadiazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, in particular furan, pyrrole, thiophene and indole.
For the purposes of the present application, alkoxy should be taken to mean residues of the formula OR′, wherein R′ denotes an alkyl residue in accordance with the above-stated definition.
For the purposes of the present application, aryloxy should be taken to mean residues of the type OR″, in which R″ denotes an aryl residue in accordance with the above-stated definition.
For the purposes of the present application, acyl should be taken to mean an aliphatic, olefinic or aromatic carboxylic, carbonic, carbamic, sulfonic, amidosulfonic, sulfinic, phosphoric, phosphonic or phosphonous acid residue.
For the purposes of the present application, substituents which may be considered are aryl, alkyl, alkoxy, aryloxy, acyl, acyloxy, acylamino, hetaryl, alkynyl, hydroxy, cyano, carboxy, sulfo and halogen, such as preferably fluorine, chlorine or bromine.
For the purposes of the present application, an electron-attracting group is an optionally substituted carboxy, carbamoyl, acyloxy, oxycarbonyl, halogenated alkoxy, halogen-ated aryloxy, aryloxy, acyl sulfonyl, sulfinyl, sulfonyloxy, sulfonylmethyl, sulfamoyl, tetrazolyl, pyrrolyl, phosphonyl, halogenated alkyl, halogenated aryl, cyano, alkyl-sulfonylmethyl, arylsulfonylmethyl or a nitro group, as well as a halogen atom.
Seperable groups X
11
may comprise halogen, for example chlorine, N-linked, optionally substituted N-heteroaromatics, for example pyrazoles, imidazole, triazoles or non-aromatic heterocyclics, for example hydantoins, oxazolidinediones, S-linked aliphatic or aromatic mercaptans, for example mercaptopropionic acid, 2-acylamino-phenyl mercaptans, or O-linked aliphatic or aromatic hydroxy compounds, for example ethylene glycol, p-salicylic acid ethyl ester.
Preferably used compounds of the formula (I) are those of the formula (I-A)
in which
R
13
and R
14
mutually independently have the meaning of R
11
or R
12
,
X
12
has the meaning of X
11
and
Z
12
denotes H or a substituent.
In the compounds of the formula (II), R
21
preferably denotes alkyl, alkoxy, alkylamino, acyl, acylamino, acyloxy, hydroxy or halogen, n and m preferably denote 0 or 1, providing that n and m are not simultaneously 1, o denotes zero, 1 or 2 and p denotes zero, 1, 2 or 3. Particularly preferred compounds of the formula (II) are those of the formula (II-A)
in which
R
23
, R
24
mutually independently denote alkyl, acyl, acylamino, alkoxy, halogen, cyano or nitro,
R
25
denotes H or alkyl,
R
26
denotes H, alkyl or acyl and
r, s mutually independently denote 0, 1 or 2.
Table 1 below lists some particularly preferred compounds of the formula (I) or (I-A) by way of example.
R
13
R
14
X
12
Z
12
I-1
H
H

I-2
—S—CH
2
—CH
2
—COOH
H

I-3
Cl
H

I-4
H
H

I-5
H

I-6
C
16
H
33
—O—CO—CH
2
—CH
2
—NH—CO—
H
H

I-7
C
12
H
25
—SO
2
—C
3
H
6
—NH—CO—
—CF
3
H

I-8
H
H

I-9
H
H

I-10
C
18
H
37
—NH—SO
2
—
H
H

I-11
—CN
H
H

I-12
H
H

I-13
H

I-14
H
H

I-15
t-C
4
H
9
—NH—CO—
H
H
and
50/50 wt. %

I-16
—CN
—S—CH
2
—CH
2
—COOH
H

I-17
H
H

I-18
H
H

I-19
H
H

I-20
H
H
Some examples of the formula (II) or (II-A) which are particularly preferred according to the i

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