Eastman-kodak Company

Robert N Gourley

Bernard A Clark

Paul B Merkel

Jerrold N Poslusny

James Henry Reynolds

Paul R Buckland

Leslie Shuttleworth

Hamish McNab

Craig Cameron Sommerville

Michael H Kearns

A photographic element comprises a support bearing at least one silver halide emulsion and at least one acylacetanilide or malonanilide yellow dye-forming DIR coupler of structure I or structure II, below ##STR1## wherein the substituents are as defined in the specification.

Photographic element containing a DIR coupler

The invention provides a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a dye-forming coupler of formula (I): ##STR1## wherein X is H or a coupling-off group, R.sub.1 is H or a substituent group; Y and Z are the same or different and are H or are independently selected from alkyl, aryl and heteroaryl groups; provided that Y and Z taken together with the nitrogen atom may form a 5-10 membered heterocyclic ring.

Photographic elements containing certain yellow dye-forming couplers

This invention relates to a method for reducing a nitro group substituent on an aromatic compound to an amino group and is characterized by treatment of the compound in the presence of iron or zinc and a halogen-containing aliphatic carboxylic acid.

Method for reducing aromatic nitro groups

Disclosed are new disperse azo dyes prepared from 2-amino-cinnamoylthiophene compounds. These dyes give bright blue shades, for example, on polyester, cellulose acetate and other synthetic fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, migration, and the like. The dyes have the general formula: ##STR1## wherein each R is a substituent selected for example from alkyl, substituted alkyl, hydroxy, alkoxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, cyano, alkylamino, and dialkylamino, R.sup.14 is hydrogen or alkyl, C.sup.1 represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted, and each of R.sup.12 and R.sup.13 is hydrogen or a substituent such as acyl, acylamido, alkyl, halogen, and cyano.

2-amino-cinnamoylthiophene azo dyes having aniline, tetrahydroquinoline,

Disclosed are azo dyes containing diazonium moieties from aminothiazoles, aminoisothiazoles, or aminothiadiazoles (1,2,4- or 1,3,4-), and certain coupler moieties from aniline, tetrahydroquinoline, and benzomorpholine type compounds, wherein the diazonium moieties have at least one cinnamoyl group, and wherein a wide variety of groups, e.g., one or more water-solubilizing substituents such as sulfonic acid groups or their metal or amine salts may be present in the dye molecule. These dyes are useful for dyeing materials selected from polyamide, cellulose ester, polyester, wool and other natural and synthetic fibers and generally exhibit improvements in dyeability and fastness properties.

Disperse and acid azo dyes having one or two cinnamoyl substituents on a

Disclosed are new acid azo dyes prepared from 2-amino-cinnamoylthiophene compounds. These dyes give bright red to blue shades, for example, on polyester, cellulose acetate, wool and particularly polyamide fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, migration, and the like. The dyes have the general formula ##STR1## wherein: R.sup.14 is H or alkyl; R is a substituent selected, for example, from alkyl, substituted alkyl, hydroxy, alkoxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, cyano, alkylamino, and dialkylamino; C.sup.1 represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted; each of R.sup.12 and R.sup.13 is selected from H, alkyl, alkoxy, acyl, halogen, and the like; and at least one of the water solubilizing groups, --SO.sub.3 M or --OSO.sub.3 M is present in the dye molecule.

2-Amino-cinnamoylthiophene acid azo dye compounds having an aniline,

This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing a diazonium moieties from an aniline type compound and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moiety has one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.

This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing diazonium moieties from 2-aminobenzothiazole or 2-aminobenzisothiazole type compounds, and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moieties have one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.

Disclosed are mixtures of dyes of the formula ##STR1## wherein R is alkyl of 1-4 carbons; R.sup.1 is H or alkyl of 1-4 carbons; R.sup.2 is alkyl of 1-7 carbons, or ethoxyethoxyethyl; R.sup.3 is H or methoxy; and R.sup.4 is H, methyl, or --NHCOCH.sub.3. These mixtures exhibit improved properties such as reduced energy of application, for example, in the dyeing of polyester and cellulose diacetate or triacetate fibers and their blends with other synthetic and natural fibers.

Mixtures of azo dyes from 2-amino-3-nitro-5-acyl thiophenes and certain

Disclosed are new azo dyes from 2-amino-3,5-bisfluorosulphonyl thiophene which may be further substituted, and certain aniline, tetrahydroquinoline and benzomorpholine couplers. These dyes produce bright blue shades on hydrophobic fibres including polyesters, polyamides and cellulose esters, both by dyeing and heat transfer printing, and show improvements in one or more properties of dyeability, low energy of application, fastness to light, gas and wash, and heat stability, and have the general formula ##STR1## wherein R is hydrogen, alkyl or alkyl substituted with aryl or cycloalkyl; and C' represents an aniline, 1,2,3,4-tetrahydroquinoline, or benzomorpholine disperse dye coupling component.

Disperse azo dyes from 2-amino-3,5-bisfluorosulphonyl thiophene and

Disclosed are novel azo dyes of the structure

Azo dyes containing fluorinated carboxylic or sulphonic ester groups on

Azo dyes having the general formula: ##STR1## wherein R.sub.1 represents a substituent selected from the group consisting of hydrogen, methyl, ethyl, methoxy, ethoxy, halogen, nitro, acetyl, carbomethoxy, carboethoxy, cyano and thiocyanate, and A is an aniline, 1,2,3,4-tetrahydroquinoline or benzomorpholine coupling component, may be used as conventional disperse dyes on polyester, polyamide, acrylic, triacetate and other synthetic fabrics, and some are particularly suitable for use in the transfer printing of polyesters and polyamides.

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Formby, United Kingdom

Robert N Gourley