Eastman-kodak Company

Leslie Shuttleworth

Robert N Gourley

David Mullen

Michael H Kearns

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 novel intermediates and their preparation, and the preparation therefrom of 2-halo-3-nitro-5-acyl thiophenes which themselves are important intermediates for the preparation of azo dyes of the type, ##STR1## wherein C.sup.1 represents typically any aniline, tetrahydroquinoline, benzomorpholine or the like coupler and the acyl group contains from 1-10 carbons. It has been found that if 2-acyl thiophene is treated with a hydroxylamine compound, e.g., a salt of hydroxylamine, including sulphate, chloride or the like, to form the oxime prior to the 2-position halogenation and 3-position nitration steps, various side reactions such as halogenation of the acyl group and nitration of the 5-position are avoided, the yield of each step is improved, and the reactions are less sensitive to the deleterious effects of temperature variations and excess reactants. The oxime derivative is readily reconverted to the acyl derivative after the halogenation and nitration steps have been completed. This product is then readily aminated to give the 2-amino derivative.

Preparation of 2-halo-3-nitro-5-acyl thiophenes and intermediate

Disclosed is a process for coupling a disperse dye diazo component selected from diazonium salts of substituted and unsubstituted phenyl, 2-thiazolyl, 2-benzothiazolyl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 2,1-benzisothiazol-3-yl, isothiazol-5-yl, 1,3,4-triazol-2-yl, pyrazol-5-yl, imidazol-2-yl, phthalimid-3 or 4-yl, 1-naphthyl, and 2-thienyl radicals comprising reacting with said component a disperse dye coupler having in the coupling position on the ring a substituent typified by --CHO, --COOH, --COCH.sub.3, --SO.sub.3 H, displaceable diazonium radicals including the above, and another or the same coupler linked to said coupler by certain bivalent radicals.

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Ormskirk, United Kingdom

Leslie Shuttleworth