Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Patent
1993-06-01
1995-11-28
Wright, Lee C.
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
430386, 430387, 430388, 430389, 430558, G03C 732, G03C 738
Patent
active
054706963
DESCRIPTION:
BRIEF SUMMARY
This invention relates to photographic colour couplers and in particular to a class of couplers.
Colour couplers are known to belong to a number of classes, for example magenta dye-forming couplers can be pyrazolones, pyrazolotriazoles and pyrazolobenzimidazoles while yellow dye-forming couplers can be acetanilides. European Patent Specification 0 431 374 A describes .beta.,.gamma.-unsaturated nitriles as cyan colour couplers of the general formula:
wherein W is hydrogen or an atom or group capable of being released when the compound is subjected to a coupling reaction with oxidised product of an aromatic primary amine derivative and is attached to a carbon atom having an sp.sup.3 electronic configuration,
R.sub.1 is a substituent,
V is nitrogen or --C(R.sub.3)=,
if V represents nitrogen, R.sub.2 represents a substituent,
if V represents --C(R.sub.3)=, R.sub.2 and R.sub.3 each represent a substituent, provided that at least one of R.sub.2 and R.sub.3 represent an electron attractive substituent, and provided that if R.sub.2 or R.sub.3 represents an aliphatic group or an aromatic group, the other does not represent an acyl group, and
R.sub.1 and R.sub.2 may bond together to form a ring.
The couplers of the above general formula are said to have less subsidiary absorption in the blue region of the spectrum. In support of this contention one drawing (FIG. 1) and a table of data are provided wherein the dye formed from Coupler 53 is compared to that from Comparative Compound (1)--a phenolic coupler.
The compounds of the present invention are not cyan couplers and are distinct from those of European Specification 0 431 374A because, inter alia, the coupling position is a carbon atom having an sp.sup.2 electronic configuration and the compounds are .alpha.,.beta.-unsaturated. No examples of them appear in EP 0 431 374A, nor is any method of making them disclosed.
"Preparation and Reactions of 1,2-dicyano-1,2-disulfonylethylenes" by E L Martin, Journal of the American Chemical Society, Aug. 20, 1963 at page 2449, describes compounds of the formula:
The method of preparation means that only compounds having the --SO.sub.2 R can be prepared. In addition there is no disclosure of ballasted compounds.
The present invention provides a new class of couplers capable of forming dyes having good spectral characteristics such as maximum wavelength (.lambda..sub.max) and half-band width, little unwanted absorption of blue light and good fastness properties. Both magenta and yellow dye formation has been observed.
According to the present invention there are provided photographic elements comprising a support, at least one photosensitive silver halide layer and in or adjacent said silver halide layer a colour coupler of the general formulae: ##STR2##
wherein A and B represent the same or different electron-withdrawing group,
X is H or a group which splits off on coupling with oxidised colour developer,
R is an alkyl, cycloalkyl, aryl or heterocyclic group any of which may be substituted, --COR.sup.1, --CSR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, --NHCOR.sup.1, --CONHR.sup.1, --COOR.sup.1, --COSR.sup.1, --NHSO.sub.2 R.sup.1 wherein R.sup.1 is an alkyl, cycloalkyl, or aryl group any of which are optionally substituted, and wherein two or more of A, B, R, and X optionally form part of a ring,
Link is a linking group and
n is 0, 1 or 2.
In one embodiment A and B together complete an electron-withdrawing heterocycle which may be substituted. In another embodiment R and X together complete a heterocyclic ring which is optionally substituted.
It is noted that formulae (1) and (2) represent geometric isomers (cis and trans versions) of the same compound.
BRIEF DESCRIPTION OF DRAWINGS
FIG. 1 is a plot of absorbents vs wavelength for the dyes obtained from coupler C-3 and control 1 (dotted line).
The advantages of the present invention include the provision of couplers of good activity capable of forming dyes having good spectral characteristics such as maximum wavelength (.lambda..sub.max) and half-band width, little unwanted absorpti
REFERENCES:
patent: 4404273 (1983-09-01), Forte et al.
patent: 4661437 (1987-04-01), Tschopp
patent: 5047314 (1991-09-01), Sakai et al.
patent: 5206129 (1993-04-01), Sato et al.
"Preparation and Reactions of 1,2-dicyano-1,2-disulfonylethylenes" by E. L. Martin, Journal of the American Chemical Society, Aug. 20, 1963 at p. 2449.
Eastman Kodak Company
Kluegel Arthur E.
Wright Lee C.
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