Radiation imagery chemistry: process – composition – or product th – Color imaging process – Using identified radiation sensitive composition in the...
Patent
1986-05-01
1988-03-01
Schilling, Richard L.
Radiation imagery chemistry: process, composition, or product th
Color imaging process
Using identified radiation sensitive composition in the...
430386, 430544, 430548, 430551, 430558, G03C 140, G03C 738
Patent
active
047285982
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a new class of photographic color couplers comprising an imidazo[1,2-b]pyrazole nucleus, to photographic materials containing them and to a method of forming a dye image in such photographic materials.
A number of nitrogen-containing heterocyclic compounds have been proposed for color couplers. Pyrazolone couplers, for example, are widely used as maganta dye-forming couplers. Other couplers are described in Bailey and Williams, "The Photographic Color Development Process" in the Chemistry of Synthetic Dyes, ed. K. Venkataraman, Academic Press, Inc., New York and London, Volume 4, 341 (1971). Further couplers are the pyrazolo[3,2-c]-s-triazoles and imidazo[1,2-b]-s-triazoles described in The Theory of the Photographic Process, ed. T. H. James, Macmillan, New York, page 358 (1977) and Research Disclosure No. 16216, 1977, 73-75 respectively.
Research Disclosure 24531 (September 1984) published by Industrial Opportunities Ltd., The Old Harbourmaster's, 8 North Street, Emsworth, Hants PO10 7DD, U.K. contains, inter alia, a reference to couplers of the general formula: ##STR1## wherein X.sub.2 is hydrogen or a coupling-off substituent while R.sub.3, R.sub.4 and R.sub.5 are hydrogen or one of a number of specified substituents. Structural formulae of specific couplers within this general formula are listed but no examples of their preparation or use are given.
The present invention provides novel dye-forming color couplers.
According to the present invention there is provided a photographic color coupler which comprises an imidazo[1,2-b]pyrazole nucleus and which reacts at its 3-position with an oxidized aromatic primary amino color developing agent.
Preferred couplers have the general formula: ##STR2## in which R.sub.1 and R.sub.2 are each hydrogen or a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic, hydroxy, nitrile, sulfone, acylamido, sulfonamide, sulfamoyl, alkoxycarbonyl, aryloxycarbonyl or nitro group, an amino or substituted amino group, a carbamoyl or substituted carbamoyl group, a non-coupling-off alkoxy group or a non-coupling-off phenolic stabilizer moiety, represent and is not hydrogen, and contains an ethylenically unsaturated polymerisable group.
It is known that pyrazolotriazole (PTs) and pyrazolobenzimidazole (PBIs) dyes have better absorption characteristics (viz. less blue absorption) than the corresponding pyrazolone dyes. The dyes from the couplers of the present invention also have good absorption properties, and since they have only two fused rings compared with the PBIs which have three, they have, in consequence, better solubility and thus are easier than PBIs to disperse in photographic emulsions. Furthermore, the couplers of the present invention in comparison with PT couplers have one extra site to carry an additional substittuent. This extra substituent can be used through electronic and steric effects to finely control parameters such as pK.sub.a and reactivity. Hence higher activity couplers can be obtained from this new series of compounds. The absorption .lambda.max can also be varied; the examples below show .lambda.max variations from 529-620 nm.
Examples of substituents R.sub.1, R.sub.2 and R.sub.3 include alkyl radicals which may have a straight or branched chain and may be substituted and preferably contain 1-22 carbon atoms, e.g. methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-pentyl, n-hexyl or 2-aminoethyl; aryl radicals which may be substituted, e.g. phenyl, 4-methylphenyl; heterocyclic radicals e.g. pyridyl or thienyl; amino, methylamino, diethylamino, phenylamino; acylamido radicals e.g. ethylcarbonamido, n-decylcarbonamido, phenylethylcarbonamido, phenylcarbonamido; non-coupling alkoxy group or a non-coupling phenolic stabilizer moiety, e.g., as described in U.S. Pat. No. 3,519,429 (equivalent U.K. Specification No. 1,183,515). It is preferred that R.sub.3 represents a substituent which cannot be replaced by oxidized color developing agent, that is, not a coupling-off grou
REFERENCES:
Research Disclosure, Sep. 1974, Item No. 24531, pp. 442-454.
"The Theory of the Photographic Process", edited by T. H. James, Macmillan, N.Y., N.Y., p. 358 (1977).
"The Photographic Color Development Process" by Bailey and Williams in Chemistry of Synthetic Dyes, edited by K. Venkataraman, Academic Press Inc., N.Y. and London, vol. 4, p. 341 (1971).
Research Disclosure, Oct. 1977, Item No. 16216, pp. 73-76.
Research Disclosure, Dec. 1978, Item No. 17643, pp. 22-31.
Research Disclosure, Jun. 1984, Item No. 24220, pp. 253-258.
Bailey Joseph
Rogers David N.
Eastman Kodak Company
Knapp Richard E.
Schilling Richard L.
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