Radiation imagery chemistry: process – composition – or product th – Nonradiation sensitive image processing compositions or...
Patent
1994-01-03
1995-10-24
Wright, Lee C.
Radiation imagery chemistry: process, composition, or product th
Nonradiation sensitive image processing compositions or...
430385, 430386, 430543, 558 44, 558395, G03C 732
Patent
active
054609275
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The present invention relates to activated propenes as color couplers and to a method for their production. The invention particularly relates to magenta color couplers for use in silver halide imaging systems where dyes are formed by oxidative coupling within a photographic layer. Previously pyrazolone couplers such as that described in U.S. Pat. No. -A-2,600,788 have been used. However such pyrazolones are so reactive that the efficiency of dye formation is reduced due to side reactions during photographic processing. Further they require difficult methods of synthesis and have the additional problem of a substantial secondary adsorption peak in the visible spectrum which has an adverse effect on color reproduction.
This problem has been addressed in U.S. Pat. No. -A-4,871,652 by the production of complex cynano-substituted couplers which overcome some of these disadvantages.
A further problem is to produce the activated propenes economically from readily available compounds and with a short reaction sequence.
Our copending British Patent Application No. WO-A-9209010 relates in a first aspect to a photographic composition comprising as a ballasted coupler a propene isomer of the formula ##STR3## wherein A B and E, each individually represent hydrogen or an electron withdrawing group;
D represents a substituent incorporating a lone pair of electrons, and X is hydrogen or a group releasable during a photographic coupling reaction.
The electron withdrawing group may be selected from selected from hydrogen, --CN, --NO.sub.2, --SO.sub.2 R, --SO.sub.2 NH--, --CO.sub.2 R, --COR, --CONHR, --CF.sub.3 halogen, amino aryl, aralkyl, alkyl, cycloalkyl, alkyl (carbonyl)oxy, aryl (carbonyl)oxy, carboxy, alkoxycarbonyl, aryloxycarbonyl, carbamomyl, acyl, alkylaminocarbonyl, arylaminocarbonyl, alkoxycarbonylamino, acylamino, ureido, alkylsulphonylamino, arylsulphonylamino, sulphamoylamino, alkylsulphonyl, arylsulphonyl, sulphamoyl, imido, alkylthio, arylthio or a heterocycle;
Examples of the substituent D incorporating the lone pair of electrons are --NH.sub.2, --NHR, --NR.sup.1 R.sup.2, --OR, --SR, alkyl (carbonyl) oxy, aryl (carbonyl)oxy, carbamoyl, alkoxycarbonylamino, acylamino, ureido, alkylsulphonylamino, or an arylsulphonylamino group.
In a further aspect of the copending application there is provided a propene isomer of the formula ##STR4## wherein the substituents A, B, E and X are as above defined but wherein D is a group of the formula Ar-L-wherein Ar is a phenyl group optionally substituted with one or more substituents and -L- is a linking group incorporating a lone pair of electrons.
Examples of substituents on Ar are: halogens, --CN, --NO.sub.2 , --SR, --SO.sub.2 R, --SO.sub.2 NHR, --OR, --OCOR, --CO.sub.2 R, --COR, --CONHR, --CO.sub.2 H, --NHR, --NR.sup.1 R.sup.2, --NHSO.sub.2 R, --NHCO.sub.2 R, --NHCONHR, --CF.sub.3, aryl, aralkyl, alkyl and cycloalkyl.
Examples of -L- are: --NH--, --NR--, --N(COR)--, --NHCONH--, --S--, --SO--, --SO.sub.2 --, --SO.sub.2 0--, --0-- and --(CO)0)0--.
The groups hereinbefore designated R, R.sup.1 and R.sup.2 are each defined as alkyl or aryl, any of which may be substituted.
U.S. Pat. No. -A-3,079,366 reveals a method for the production of propenes for use as ultraviolet absorbing compounds with plastics materials;
U.S. Pat. No. -A-2,719,861 relates to the manufacture of malononitrile dimer, while EP-A-0,431,374 relates to color couplers and elements containing them.
According to the present invention therefore there is provided a method for the production of a photographic element comprising an activated propene as a color coupler which method comprises reacting a compound of the formula (I) ##STR5## with a nucleophile D to provide a compound of the formula (II) ##STR6## wherein A, B and E each individually represent hydrogen, a substituted or unsubstituted alkyl, acyl, carboxy or aryl group or an electron withdrawing group and X is a group capable of displacement via a substitution reaction, and incorporating the same into a photographic element.
The method of
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Eastman Kodak Company
Kluegel Arthur E.
Wright Lee C.
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