Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2001-07-20
2003-04-15
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S502000, C430S627000, C430S628000, C430S630000, C430S629000, C430S557000, C430S543000
Reexamination Certificate
active
06548238
ABSTRACT:
The present invention relates to a colour photographic material which comprises at least one spectrally sensitised AgX emulsion layer as well as at least one additive for improving the stability of dyes.
Colour photographic materials usually contain at least one yellow coupler, at least one magenta coupler and at least one cyan coupler, from which the corresponding dyes are formed by exposure and development. These dyes, particularly dyes which are continuously exposed to light, should exhibit high colour stability, and particular value is placed on the colour stability of all three colours being as good and as identical as possible, so that slight fading does not give rise to colour distortion. In particular, yellow dyes which are produced from couplers containing an open chain ketomethylene grouping have to be stabilised both from light and from fading in the dark. It is known from EP 317 983 that polyacrylamides can be added to yellow couplers; this does not always result in sufficient stability in the dark, however.
There is thus a continuing need for dyes which exhibit improved stability to light.
The underlying object of the present invention is therefore to produce colour photographic materials which are distinguished by their high stability to light.
This object is achieved by the addition of defined polyvinylcaprolactams.
The present invention relates to a colour photographic material which contains at least one light-sensitive silver halide emulsion layer, and which, in at least one layer which contains a colour coupler, contains at least one homo- or copolymer which comprises a monomer unit of formula (II)
wherein the monomer unit (II) amounts to at least 10% by weight in copolymers.
The coupler preferably corresponds to formula (I)
where
R
11
and R
12
, independently of each other in each case, represent alkyl, or R
11
and R
12
can jointly form a ring system,
R
13
represents H or has the meaning of R
11
or R
12
,
R
14
represents H, alkyl or halogen,
X
11
represents halogen or alkoxy,
X
12
represents acyl, acylamino, halogen, sulphonamido or sulphamoyl,
Z
11
represents a group of formula
and Q
11
represents an organic group for the completion of a 5- or 6-membered ring, and preferably denotes imidazole, 1,3,4-triazole, oxazoledione or hydantoin derivatives.
The monomer unit in copolymers preferably amounts to at least 40% by weight.
Suitable comonomers include esters of acrylic acid, esters of methacrylic acid, vinyl esters, vinyl ethers, olefines and methacrylamides. Methacrylamides are preferably used in amounts up to 50% by weight only.
The preferred comonomers are esters of acrylic acid, e.g. ethyl, butyl and hydroxyethyl acrylates.
The polymers can be produced by customary methods of radical, homo- or copolymerisation. The average molecular weight (weight average) of the polymers ranges between 2000 and 1,000,000, particularly between 2000 and 400,000, most preferably between 10,000 and 150,000.
In addition, at least one compound of formula (III) can be used
where
R
21
represents H or alkyl,
R
22
represents H, alkyl or aryl, and
R
23
and R
24
, independently of each other in each case, represent an aryl, a secondary alkyl or a tertiary alkyl.
The term “alkyl” in the sense of the present Application is to be understood to mean linear, branched, or cyclic hydrocarbon radicals. The latter can themselves be substituted, for example with a halogen, hydroxy, alkoxy, aryl, arloxy, acyl, acyloxy, acylamino, sulpho, carboxy or cyano group. The R
11
and R
12
radicals are preferably alkyl radicals containing 1 to 4 C atoms.
The term “aryl” in the sense of the present Application is to be understood to mean aromatic hydrocarbon radicals, such as benzyl or naphthyl for example, which can themselves be substituted, for example with a halogen, hydroxy, alkyl, alkoxy, aryloxy, acyl, acyloxy, acylamino, sulpho, carboxy and cyano group.
Acyl radicals in the sense of the present Application are to be understood to mean radicals of saturated or unsaturated aliphatic or aromatic carboxylic, carbonic, carbamic, sulphonic, amidosulphonic, phosphoric, phosphonic, sulphinic or phosphorous acids.
The term “halogen” in the sense of the present Application is to be understood to mean fluorine, chlorine, bromine and iodine, particularly chlorine and bromine.
In one preferred embodiment, R
14
represents H, X
11
represents chlorine or alkoxy, X
12
represetns alkoxycarbonyl or alkylcarbonylamino, R
21
represents hydrogen or methyl, R
22
represents hydrogen, methyl, phenyl or 4-alkoxyphenyl. Particularly preferred embodiments of formula (I) correspond to formulae (Ib) or (Ic)
where
R
15
and R
16
can represent methyl or R
15
and R
16
can jointly form a 3- to 6-membered, carbocylic ring,
R
17
represents H or methyl,
Z
12
has the same meaning as Z
11
,
X
13
represents chlorine or alkoxy, and
R
18
represents alkyl.
Particularly preferred compounds of formula (III) are those of the following formula (IIIa)
where
R
25
and R
27
, independently of each other, represent H or alkyl,
R
26
and R
28
, independently of each other, represent alkyl,
X
21
represents alkoxy, acyl, acylamino, alkylamino or acyloxy, and
X
22
represents H or has the same meaning as X
21
with the proviso that X
21
and X
22
can jointly form a 5- to 6-membered ring, and wherein (IIIa) contains no hydroxyphenol substituents.
R
15
, R
16
, R
17
, R
25
, R
26
, R
27
and R
28
preferably denote CH
3
.
Typical examples of compounds of formula (I) according to the invention are listed below:
Examples of compounds II according to the invention include:
II-1 polyvinylcaprolactam
II-2 a copolymer of vinylcaprolactam and ethyl acrylate (50% by weight of each)
II-3 a copolymer of 50% by weight vinylcaprolactam, 40% by weight t-butylacrylamide and 10% by weight hydroxyethyl acrylate
II-4 a copolymer of 75% by weight vinylcaprolactam and 25% by weight t-butylacrylamide
II-5 a copolymer of 95% by weight vinylcaprolactam and 5% by weight
Typical examples of formula (III) according to the invention are listed below:
According to the invention, the photographic material can contain compounds of formula (I) in an amount from 100 to 3000, preferably 200 to 1500, particularly 300 to 1000 mg/m
2
.
The compounds of formula (II) can be contained in the photographic material in a ratio by weight from 1:20 to 10:1, preferably in a ratio by weight from 1:10 to 2:1, with respect to the compound of formula (I).
The compounds of formula (III) can be contained in a ratio by weight from 1:20 to 2:1 with respect to the compound of formula (I). They are preferably contained in a ratio by weight from 1:10 to 1:1.
In addition, high-boiling organic solvents and other polymers can be used, e.g. those which are known from DE-OS 25 35 497 and U.S. Pat. No. 4,857,449.
In one particularly preferred embodiment, phenolic image stabilisers of formula (IV) are also used in addition,
where
R
a
, R
b
, R
d
, R
e
represent H, alkyl, aryl, aralkyl, acylamino, acyl or halogen, and
R
c
represents alkyl, aryl, aralkyl, acyl or acylamino.
Some typical examples are listed below:
Examples of colour photographic materials include colour negative films, colour reversal films, colour positive films, colour photographic paper, colour reversal photographic paper, and colour-sensitive materials for the colour diffusion transfer process or the silver halide bleaching process. Reviews thereof are given in Research Disclosure 37038 (1995) and in Research Disclosure 38957 (1996).
Photographic materials consist of a support on which at least one light-sensitive silver halide emulsion layer is deposited. Thin films and foils are particularly suitable as supports. A review of support materials and of the auxiliary layers which are deposited on the front and back thereof is given in Research Disclosure 37254, Part 1 (1995), page 285 and in Research Disclosure 38957, Part XV (1996), page 627.
Colour photographic materials usually contain at least one red-sensitive, at least one green-sensitive and at least one blue-sensitive silver halide emulsion layer
Spachmann Bernd
Weber Beate
Wiesen Heinz
AGFA-Gevaert
Connolly Bove & Lodge & Hutz LLP
Letscher Geraldine
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