Acetanilide couplers

Details Acetanilide couplers Acetanilide couplers

1999-11-24

2001-10-02

Morris, Patricia L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06297385

ABSTRACT:

This invention relates to new yellow couplers for colour photograhic materials.
This invention further relates to a colour photographic material containing the new yellow couplers.
It is known that the blue-sensitive silver halide layer of a photographic material can be provided with 2-equivalent yellow couplers. Compared with the 4-equivalent couplers which were more frequently used hitherto, 2-equivalent couplers are characterised in that they only require about half as much silver halide for the formation of a given amount of dye. This has the advantage that the amount of silver halide in the material can be reduced, which results in thinner emulsion layers and thus at the same time results in better resolution and sharpness of the colour photographic material.
Amongst other factors, the photographic properties of a coupler are determined by the volatile group. There is a multiplicity of different volatile groups which are also known from the prior art for yellow couplers. Apart from halogens, some heterocyclic compounds which have already been used successfully. The volatile (groups should be both photographically inert and readily obtainable synthetically.
In addition to the volatile groups, however, the other substituents on the yellow coupler also have a considerable effect on the photographic properties. Thus benzoyl acetanilide couplers, which are very active as regards coupling, are usually employed in negative materials, for example. A disadvantage of this class of couplers, however, is the poor dark fading stability of dyes formed from these couplers.
In contrast, and as is known from the prior art, pivaloyl acetanilide couplers exhibit a high dye stability, but only exhibit a relatively low reactivity, which results in low colour density, film speed and gradation values. Therefore, pivaloyl acetanilide couplers are usually less suitable for use in CN films.
2-equivalent yellow couplers are known from DE-OS 2442703 which contain, as a volatile group, a 5-membered heterocyclic compound which is bonded via a nitrogen atom and which contains at least 2 nitrogen atoms. According to the disclosure of DE-OS 2442703, compounds such as these are characterised by a good shelf life and a high coupling capacity. However, it has been shown that, due to their sulphonamide substitution, compounds according to DE-OS 2442703 exhibit relatively broad half-band widths and there is a bathochromic shift in the absorption maximum.
In order to obtain couplers which satisfy current requirements, it is therefore necessary to achieve the optimum combination of the various substituents.
The underlying object of the present invention is to identify yellow couplers for photographic film materials which firstly exhibit a high dye stability, especially a high dark fading stability such as that which is described in the prior art for pivaloyl couplers in particular, and which at the same time exhibit good coupling kinetics, preferably such as those which are known from the prior art for benzoyl couplers. In particular, the yellow couplers according to the invention should have a half-band width which is as low as possible.
Surprisingly, it has been found that compounds of formula (I) exhibit both the good coupling kinetics which are required for use in photographic film materials, particularly CN film, and also at the same time exhibit good dark fading stability. Moreover, both the couplers themselves and the dyes formed therefrom are distinguished by their good tropical stability. In addition, the couplers according to the invention exhibit a low half-band width. Opaque display and reversal materials which contain compounds of formula (I) according to the invention are therefore characterised by their brilliant colour reproduction.
According to the present invention, the half-band width is to be understood as the band width of the absorption band at 50% of an absorption which is put at 100%.
According to the present invention, the tropical stability is to be understood as the stability at a temperature in the region of 35° C. and at a relative atmospheric humidity in the region of 90%.
The present Application relates to new yellow couplers of formula (I),
wherein
R
1
represents alkyl or hetaryl,
R
2
represents halogen, alkoxy, aryloxy,
R
3
represents alkoxycarbonyl (—COOR′), carbamoyl (—CONHR′R″), urethane (—NHCOOR′),
R
4
represents a substituent,
R
5
represents alkyl or aryl and
R
6
represents hydroxy-(ethyloxy)
n
, where n=1 to 2.
Alkyl in the sense of the present Application is to be understood to mean linear or branched, cyclic or straight chain, substituted or unsubstituted hydrocarbon groups, preferably alkyl groups containing 1 to 22 C atoms, particularly 1 to 6 C atoms. Open-chain groups which are particularly suitable include methyl, ethyl, n-propyl and n-butyl. Branched alkyl radicals which are especially suitable include 2-hexyl-decyl and 2-ethylhexyl radicals, and t-butyl in particular. The preferred cycloalkyl groups include cyclohexyl groups such as 4-t-butyl-cyclohexyl and 2.6-di-t-butyl-4-methylcyclolhexyl for example, and particularly cyclopropyl groups such as ethylcyclopropyl for example.
Unless defined otherwise, hetaryl in the sense of the present Application is to be understood to mean aromatic systems which contain at least one hetero atom. These systems can comprise both substituted and unsubstituted ring systems. Typical examples include pyridine, pyrimidine, pyrazine, oxazole, isoxazole, thiazole, 3,4-oxadiazole, 1,2,4-oxadiazole, imidazole, indole, 1,2,3-thiazole and 1,2,4-triazole. Indolyl is particularly preferred.
Halogen in the sense of the present Application is to be understood to mean fluorine, chlorine or bromine in particular. Chlorine is particularly preferred.
Alkoxy in the sense of the present Application is to be understood to mean substituents of formula OR in which R represents an alkyl radical with the meaning given above. Examples thereof include methoxy, ethoxy, propoxy or butoxy substituents.
Aryloxy in the sense of the present Application is to be understood to mean substituents of formula OR in which R represents an aryl radical corresponding to the definition given below. Examples of aryloxy groups include phenoxy or napthoxy substituents.
R′ and R″ can represent any alkyl radical such as those cited above, and preferably comprise linear or branched, saturated or unsaturated alkyl radicals containing 8 to 22, particularly 10 to 18 C atoms.
Unless defined otherwise, a substituent in the sense of the present Application comprises H, a halogen, particularly fluorine, chlorine or bromine and alkyl, alkoxy, acylamino, carbamoyl, alkoxycarbonyl, aryl, aryloxy, hetaryl and alkenyl substituents, as well as CF
3
or CN.
Aryl in the sense of the present Application is to be understood to mean aromatic hydrocarbon groups, preferably 5- or 6-membered ring systems which can be present as monocyclic ring systems or as condensed ring systems. These ring systems can comprise both substituted and unsubstituted ring systems. Phenyl and naphthyl groups are particularly preferred, for example.
R
1
preferably represents an alkyl group. Tert-butyl is particularly preferred. R
2
preferably represents a halogen, particularly Cl, or a methoxy group. R
3
preferably represents alkoxycarbonyl, carbamoyl or urethane entities which contain linear or branched hydrocarbons which preferably comprise 10 to 18 carbon atoms. The preferred substituents R
4
are F, Cl, Br, alkyl, alkoxy, acylamino, carbamoyl and alkoxycarbonyl. R
4
most preferably represents H. In one preferred embodiment, R
5
represents a linear, saturated alkyl radical, particularly a butyl radical, or an aryl radical, particularly phenyl.
The present invention further relates to a colour photographic silver halide material comprising at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler, at least one green-sensitive silver halide emulsion layer containing at least one magenta coupler, and at least one red-sensitive si

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