Color photographic silver halide material

Details Color photographic silver halide material Color photographic silver halide material

2000-08-09

2002-06-11

Letscher, Geraldine (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Silver compound sensitizer containing

C430S551000, C430S502000, C430S543000, C430S621000, C430S622000

Reexamination Certificate

active

06403296

ABSTRACT:

This invention relates to a colour photographic silver halide material having improved properties.
Practical requirements placed upon DOP scavengers (scavenging reagents for the developer oxidation product) in colour photographic silver halide materials (colour film and colour paper) are:
a) elevated efficiency, i.e. effective avoidance of unwanted co-coupling,
b) elevated storage stability, i.e. avoidance of loss of activity by oxidation prior to processing;
c) no impairment of image stability, i.e. in film for example avoidance of post-coupling, in paper for example stability of the dyes to the action of moisture, heat and light.
So-called white couplers or redox-active compounds are used to perform these tasks. Such compounds conventionally comprise pyrazolone couplers having a methyl group at the coupling site or diffusion-resistant hydroquinones, disulfone amido-phenols and N-aryl-N′-acylhydrazines. However, these compounds are incapable of adequately fulfilling practical requirements as described above. Better results are achieved with certain benzofuranones.
However, when these compounds are used, an increase in magenta fog is observed on storage of exposed and processed materials under tropical conditions.
It has surprisingly now been found that said increase in magenta fog disappears if vinylsulfonyl hardeners are used.
The present invention accordingly provides a colour photographic silver halide material containing gelatine, comprising a support and at least one photosensitive silver halide emulsion layer and at least one non-photosensitive layer, which material contains at least one compound of the formula (I) or (II) and is hardened with a vinylsulfonyl compound
in which
R
1
means hydrogen, alkyl or acyl,
R
2
, R
3
mutually independently mean alkyl, cycloalkyl, alkenyl, aryl, halogen, OR
4
, SR
5
, NR
6
R
7
, nitro, cyano, SO
2
R
8
, COOR
9
, COR
10
or hetaryl,
R
4
, R
5
, R
9
mutually independently mean alkyl, cycloalkyl, alkenyl, aryl or hetaryl,
R
6
, R
7
mutually independently mean H, R
4
, COR
10
, COOR
9
, SO
2
R
8
,
R
8
, R
10
mutually independently mean alkyl, cycloalkyl, alkenyl, aryl, hetaryl or NR
6
R
7
,
n, m mean 0, 1, 2, 3 or 4,
wherein two residues R
2
or R
3
may in each case mean a fused carbo- or heterocyclic ring or the compound of the formula I is attached to a polymer chain via one of the residues R
1
, R
2
or R
3
,
 in which
R
11
, and R
12
mutually independently mean alkyl, cycloalkyl, aryl, halogen, SR
5
, NR
6
R
7
, nitro, cyano, SO
2
R
8
, COOR
9
, COR
10
, hetaryl or hydrogen and
R
13
and R
14
mutually independently mean OR
15
or have the meaning of R
11
,
R
5
, R
6
, R
7
, R
8
, R
9
and R
10
have the above-stated meaning,
R
15
means hydrogen, alkyl or aryl,
o means 0, 1, 2, 3 or 4 and
p means 0, 1, 2, or 3,
wherein two residues R
13
or R
14
may in each case mean a fused carbo- or heterocyclic ring or the compound of the formula II is attached to a polymer chain via a residue R
13
or R
14
.
Acyl residues R
1
may be residues of an aromatic or aliphatic carboxylic, carbamic, carbonic, sulfonic, sulfinic or phosphoric acid.
Preferably, at least one of the residues R
2
and R
3
is in para position relative to the phenolic oxygen.
Incorporation into a polymer chain may proceed via an unsaturated group, for example a styrene, acrylic acid or methacrylic acid group. One suitable monomer of the formula (I) is for example
The attachment of the formula I to a polymer may furthermore proceed by means of a polymer-analogous reaction. For example, the following compound
may be attached to a polymer:
In a preferred embodiment, each R
2
is identical to an R
3
and n equals m.
Preferably, R
1
means hydrogen or acyl, R
2
and R
3
mean alkyl, wherein the total number of C atoms in the alkyl residues R
2
and R
3
is ≧8. Preferred acyl residues are the residues of aromatic and aliphatic carboxylic acids. n and m are preferably 1 or 2.
Preferably, R
11
, and R
12
means hydrogen or alkyl and R
13
and R
14
mean alkyl, wherein the total number of C atoms in the alkyl residues R
13
and R
14
is ≧8. o and p are preferably 0, 1 or 2.
Examples of compounds of the formula (I), in which R
1
is hydrogen, are:
No.
R
2
═R
3
I-1
4-t-C
4
H
9
I-2
4-t-C
8
H
17
I-3
4-i-C
12
H
25
I-4
4-Cyclohexyl
I-5
2-CH
3
-4-CH
3
I-6
2-t-C
5
H
11
-4-t-C
5
H
11
I-7
2-t-C
4
H
9
-4-(CH
2
)
2
CO
2
CH
3
I-8
2-t-C
4
H
9
-4-OCH
3
I-9
2-Cl-4-Cl
I-10
2-NHCO-i-C
7
H
15
-4-O-COOC
2
H
5

I-11

I-12
2-S(CH
2
)
11
CH
3
-4-CH
3

I-13

1-14
4-CO
2
C
12
H
25
I-15
3-CH
3
-4-CH
3
The position of the substituents is relative to the oxygen. Position is 3 is in para position relative to the 2
nd
ring linkage.
I-16

I-17

I-18

I-19

I-20

I-21

I-22

I-23

I-24

I-25

I-26

I-27

I-28

I-29

I-30
Examples of compounds of the formula (II), in which R
11
, and R
12
are hydrogen atoms, are:
No.
R
14
R
13
II-1
2,4-dimethyl
H
II-2
2,4-di-tert.-butyl
H
II-3
4-t-octyl
3,4-dimethyl
II-4
2,4-di-tert.-pentyl
3,4-dimethyl-4-hydroxy
II-5
2-methyl-4-(2-ethylhexyloxy)-
4-methyl
carbonamido
II-6
2,4-dicyclopentyl
3,5-dimethyl-4-acetoxy
II-7
2,4-di-tert.-butyl
4-tert.-butyl
II-8
4-iso-dodecyl (mixture)
H
II-9
2-methyl-4-tert.-octyl
4-methoxy
II-10
2,4-dimethyl
3,4-diisopropoxy
II-11
2,4-diisononyl
H
II-12
4-methyl
3,5-di-tert.-butyl-4-hydroxy
II-13
2-tert.-butyl-4-methoxy
3,4-dimethyl
II-14
3-C
15
H
31
4-hydroxy
II-25
4-methyl
4-iso-C
13
H
27
—O (mixture)
The position of the substituents R
14
is relative to the oxygen, the position of the substituents R
13
is relative to the linkage site of the phenyl residue.
Further examples are:
The use of benzofuranones as DOP scavengers is known from EP 871 066. Compounds of the formula II are preferred.
The vinylsulfonyl hardeners are of the formula (III)
L—(SO
2
—CH═CH
2
)
n
  (III)
in which
L means an n-valent group having 1 to 24 C atoms and n means 2, 3 or 4.
L preferably contains 1 to 8 C atoms and n=2.
Suitable vinylsulfonyl hardeners are described in
Research Disclosure
37254, part 9 (1995), page 294, 37038, part XII (1999), page 82 and 38957, part IIB (1996), page 599.
The vinylsulfonyl hardeners of the formula (III) may also be used in combination with other hardeners described in the above publications and preferably constitute at least 50 mol % of such combinations.
Examples of particularly suitable hardeners of the formula (III) are:
III-1 CH
2
═CH—SO
2
CH
2
SO
2
—CH═CH
2
III-2 CH
2
═CH—SO
2
CH
2
CH
2
SO
2
—CH═CH
2
III-3 CH
2
═CH—SO
2
CH
2
OCH
2
SO
2
—CH═CH
2
III-4 CH
2
═CH—SO
2
CH
2
CONHCH
2
CH
2
NHCOCH
2
SO
2
—CH═CH
2
III-5 CH
2
═CH—SO
2
CH
2
CONH(CH
2
)
3
NHCOCH
2
SO
2
—CH═CH
2
III-6 CH
2
═CH—SO
2
CH
2
CH(OH)CH
2
SO
2
—CH═CH
2
III-7 Reaction product of C(CH
2
SO
2
—CH═CH
2
)
4
and H
2
NCH
2
CH
2
SO
3
K in a molar ratio of 1.7:1.
The compounds of the formulae (I) and (II) are preferably used in a quantity of 10 to 1000 mg/m
2
, in particular of 20 to 500 mg/m
2
, of the layer concerned.
The vinylsulfonyl hardeners are preferably used in a quantity of 0.1 to 5 wt. %, in particular of 0.5 to 2 wt. %, relative to the gelatine.
The compounds of the formula (I) may also be present in salt form (phenolate); suitable cations are metal cations and ammonium ions, in particular alkyl metal ions and trialkyl- or tetraalkylammonium ions.
The compounds of the formula (I) and (II) are in particular used in at least one non-photosensitive layer.
Examples of colour photographic materials are colour negative films, colour reversal films, colour positive films, colour photographic paper, colour reversal photographic paper, colour-sensitive materials for the dye diffusion transfer process or the silver dye bleaching process.
The photographic materials consist of a support onto which at least one photosensitive silver halide emulsion layer is applied. Thin films and sheets are in particular suitable as supports. A review of support materials and the auxiliary layers applied to the front and reverse sides of which is given

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