Hydroquinone derivatives as scavengers for oxidized developer

Details Hydroquinone derivatives as scavengers for oxidized developer Hydroquinone derivatives as scavengers for oxidized developer

2002-01-07

2002-10-01

Baxter, Janet (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Silver compound sensitizer containing

C430S546000, C430S551000, C560S075000, C514S257000, C514S622000, C564S170000

Reexamination Certificate

active

06458523

ABSTRACT:

It is well known that one of the problems associated with color photography is the diffusion of the oxidized color developer away from the light sensitive silver halide emulsion layer in which it is formed into another silver halide emulsion layer, which can result in the formation of unwanted dyes at undesired places. For instance, while being generated in the green sensitive layer and forming a magenta dye through a coupling reaction with the incorporated magenta coupler, the oxidized developer can also diffuse to the red sensitive layer thereby producing unwanted cyan dye or to the blue sensitive layer thereby producing unwanted yellow dye. This kind of color formation in the wrong layers will damage the color balance of the photographic image and thus result in poor color reproduction. One way of circumventing this problem is to incorporate oxidized developer scavengers in interlayers between the light sensitive silver halide emulsion layers. These scavengers should have additional properties such as low tendency to migrate, good stability towards aerial oxidation and high solubility in photographic oils.
Hydroquinone derivatives which are useful as scavengers for oxidized developers are e. g. described in U.S. Pat. No. 4,345,016.
This invention discloses specific hydroquinone derivatives which are very effective as scavengers for oxidized developers. These compounds show good diffusion fastness and good solubility in high boiling photographic oils. They are well suited for use in photographic elements containing pyrazolotriazole couplers as magenta dye providing compounds.
This invention describes hydroquinone derivatives of the following general formula I which can be used as scavengers for the oxidized developer (also termed hereafter Dox scavengers).
Primarily, present invention pertains to a compound of the formula I
where
n is always >1, for example 2-100, preferably 2-50, especially 2-30 and in particular 2-4;
X is O or NR
4
;
if n is 2,
L is C
2
-C
25
-alkylene; C
4
-C
25
-alkylene interrupted by O, S or
 C
5
-C
12
cycloalkylene; or a group phenylene, naphthylene,
 each of which may be unsubstituted or substituted by C
1
-C
4
-alkyl;
if n is 3, L is
 when n is 4, L is
 when n is >4, L is a residue of a C
5
or C
6
sugar or a polymeric chain such as a polyvalent residue of a polyvinyl alcohol;
R
1
is H, halogen, C
1
-C
25
-alkyl, C
3
-C
25
-alkenyl, unsubstituted or by C
1
-C
4
-alkyl substituted C
5
-C
8
-cycloalkyl;
R
2
and R
3
independently of each other are C
1
-C
4
alkyl, or together with the carbon atom they are bonded to, form a carbocyclic C
5
-C
7
ring, especially C
5
-C
7
cycloalkylene;
R
4
is H or C
1
-C
18
alkyl,
R
5
is H or C
1
-C
18
alkyl or C
1
-C
25
alkanoyl,
R
6
is C
1
-C
18
alkyl or —NR
7
R
8
;
R
7
, R
8
independently are C
1
-C
18
alkyl or C
1
-C
25
alkanoyl, and
m is 1-20, especially 2-4.
Preferred compounds are of the formula I′
where
n is 2-30;
R
1
is C
1
-C
25
alkyl,
R
2
and R
3
independently are C
1
-C
4
alkyl, or together with the bonding carbon atom are C
5
-C
7
cycloalkylene,
R
4
is H,
R
5
is H,
R
6
is C
1
-C
18
alkyl,
R
7
, R
8
independently are C
1
-C
18
alkyl or C
1
-C
25
alkanoyl,
m is 2-4.
Examples for C
5
or C
6
sugars are:
Compounds of formula I are preferably used to trap the oxidized form of a developer having the following general structure:
where
A=C
1
-C
6
-alkyl;
n=1-6;
X=hydrogen, hydroxy, C
1
-C
8
-alkoxy, —COR
9
, —NHSO
2
R
10
, where R
9
and R
10
are C
1
-C
18
alkoxy and C
1
-C
8
alkyl, respectively.
Y=C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halogen;
m=0-4.
In the above structure the preferred substituents are A=—CH
2
CH
3
and n=2, X=hydrogen or —NHSO
2
CH
3
or —OH or —OCH
3
, m=0 or m 1 and Y=—CH
3
.
Examples of these are 4-amino-N,N-diethylaniline, 3-methyl-4-amino-N,N-diethylaniline, 4-amino-N-ethyl-N-&agr;-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-&agr;-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-&agr;-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-&agr;-methanesulphonamidoethylaniline, 3-methyl-4-amino-N-ethyl-N-&agr;-methoxyethyl-aniline, 3-&agr;-methanesulphonamidoethyl-4-amino-N,N-diethylaniline, 3-methoxy-4-amino-N-ethyl-N-&agr;-hydroxyethylaniline, 3-methoxy-4-amino-N-ethyl-N-&agr;-methoxyethylaniline, 3-acetamido-4-amino-N,N-diethylaniline, 4-amino-N,N-dimethylaniline, N-ethyl-N-&agr;-[&agr;′-(&agr;″-methoxyethoxy)ethoxy]ethyl-3-methyl-4-aminoaniline, N-ethyl-N-&agr;-(&agr;′-methoxyethoxy)ethyl-3-methyl-4-aminoaniline, and also the salts of such compounds, for example sulphates, hydrochlorides or toluenesulphonates.
The photographic materials according to this invention comprise a support bearing at least one layer of a light-sensitive silver halide emulsion.
Examples of color photographic materials according to this invention 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 bleach process.
Of especial interest is a color photographic recording material comprising, on a base, at least one blue-sensitive silver halide emulsion layer containing at least one yellow dye providing compound, at least one green-sensitive silver halide emulsion layer containing at least one magenta dye providing compound, at least one red-sensitive silver halide emulsion layer containing at least one cyan dye providing compound, and customary (non light sensitive) top layer(s) and interlayers separating the light-sensitive layers. The layers of the color photographic material can be arranged in various orders as is well known in the art.
The compounds of the formula I can be contained in any of the layers of the photographic material, i.e. in any of the light sensitive silver halide emulsion layers or in a non light sensitive layer. For use as a Dox scavenger, the compound of the formula I is preferably contained in one or more non light sensitive layers. In this case, the light sensitive layers may contain a lower concentration of a compound of the formula I or none.
Compounds of formula I are preferably incorporated in an interlayer adjacent to the green-sensitive layer containing a magenta coupler. Preferred color photographic materials within this invention are those wherein the magenta coupler is of the pyrazolo-azole type, e.g. as disclosed in U.S. Pat. No. 5,538,840, column 49, line 51, until column 69, line 27, and publications cited therein; this section of U.S. Pat. No. 5,538,840 is hereby incorporated by reference. Also preferred is a color photographic material, wherein the silver halide emulsion contains at least 95 mol-% AgCl.
In general, the compounds of the formula I are contained in the photographic material in an amount from 10 to 1000 mg/M
2
, especially from 30 to 500 mg/m
2
.
The compounds of formula I can be milled with polymers (e.g. PVS, polyester, polyvinyl alcohol etc.) and placed in a layer thus preventing their migration to adjacent layers. Also, compounds of formula I containing a suitable functional group (e.g. ester, hydroxy) can be reacted with a polymer, e.g. a polyvinyl alcohol or polyester, in order to attach them chemically. This form will reduce their migrating tendency.
Typical bases for the photographic material include polymeric films and paper (including polymer-coated paper). Details regarding supports and other layers of color photographic recording materials can be found in
Research Disclosure,
Item 36544, September 1994.
Essential constituents of the photographic emulsion layers are binders, silver halide particles and color couplers. Details regarding the constituents of the light sensitive layers and other (non light sensitive) layers such as top layers and interlayers separating the silver halide emulsion layers can be found in
Research Disclosure,
Item 38957, September 1996.
The invention therefore also pertains to a color photographic material comprising a com

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