Cassella Farbwerke Mainkur Aktiengesellschaft

Hoechst Aktiengesellschaft

Erwin Fleckenstein

Ernst Heinrich

Reinhard Mohr

Peter Mischke

Azo-dyestuff of the formula ##STR1## in which D represents nitrophenylene, ##STR2## DINITRO-PHENYLENE, NITRO-CYANO-PHENYLENE, NITRO-CHLORO-PHENYLENE, NITRO-BROMO-PHENYLENE, TRICHLORO-PHENYLENE, NITRO-DICHLORO-PHENYLENE, DINITRO-CHLORO-PHENYLENE, DINITRO-CYANO-PHENYLENE, NITRO-BROMO-CYANO-PHENYLENE, DINITRO-BROMO-PHENYLENE, PHENYLAZO-PHENYLENE, ##STR3## R represents hydrogen, chlorine, lower alkyl, lower alkoxy, --O--CH.sub.2 --CN, --NH--CO--lower alkyl, --NH--COO lower alkyl or ##STR4## n stands for the integer 1 or 2, X represents cyano, --CO--NH.sub.2 or --COO-lower alkyl, R.sub.1 represents hydrogen, lower alkyl, lower alkylene-OH, lower alkylene-CN, lower alkylene-OCO-lower alkyl or lower alkenyl, and R.sub.2 represents lower alkyl, lower alkylene-O-CO-lower alkyl or lower alkylene-COO-lower alkyl, said dyestuffs being suitable for the dyeing or printing of synthetic fibrous materials, such as fibers of cellulose-di-, -21/2- or -triacetat, polyamides, polyurethanes, polyolefines, polycarbonates and particularly of linear polyesters, the dyeings or prints obtained being distinguished by a very good build up, tinctorial strength and a series of very good fastness properties.

Water-insoluble monoazo-dyestuffs for synthetic fibrous materials

Compounds of the formula ##STR1## wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR.sub.1, --COR.sub.2, ##STR2## --SO.sub.2 R.sub.2, ##STR3## --CN, --NH.sub.2, --NO, --NO.sub.2 or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z.sub.1 is cyano, ##STR4## --NH--OR.sub.10, ##STR5## --OR.sub.12, --SR.sub.12 or --SO.sub.2 R.sub.12 and Z.sub.2 is chlorine, bromine, cyano, hydroxy, mercapto, --OR.sub.12, --SR.sub.12, --SO.sub.2 R.sub.12, ##STR6## --NH--OR.sub.10 or ##STR7## R.sub.1 is aliphatic; R.sub.2 is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R.sub.3 and R.sub.4 when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R.sub.3 and R.sub.4 when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R.sub.5 and R.sub.6 when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R.sub.5 and R.sub.6 when taken together with the nitrogen atom to which they are attached are heterocyclic; R.sub.7 is hydrogen, aliphatic or aromatic; R.sub.8 and R.sub.9 are aliphatic or aromatic, R.sub.10 is hydrogen, aliphatic or aralkyl, R.sub.11 is aliphatic and R.sub.12 is aliphatic, aromatic or aralkyl; R.sub.10 and R.sub.11 when taken together with the nitrogen atom to which they are attached are heterocyclic.

2,4,6-Trisubstituted-3-pyridine carboxamides

A basic dyestuff of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms in the alkyl moiety or chloroalkyl of 1 to 4 carbon atoms, R'.sub.2 is phenyl or naphthyl or is phenyl or naphthyl substituted by alkyl of 1 to 4 C-atoms and/or alkoxy of 1 to 4 carbon atoms or nitro or cyano and/or chlorine, R.sub.5 is an optionally substituted alkyl or aralkyl radical, R.sub.6 and R.sub.7 being the same or different, each is hydrogen or an alkyl radical or, both together, substituents which complete to form an anellated aromatic ring, Y is a bivalent atom or a bivalent group necessary to complete a 5- or 6-ring, R.sub.10 is hydrogen, fluorine, bromine or chlorine or alkyl of 1 to 4 C-atoms and X.sup..sup.-`is an anion, which are suitable for the dyeing or printing of tannined cellulose fibers, silk, leather or fully synthetic fibers, such as acetate silk, polyamide fibers or acid modified polyamide or polyester fibers, especially of fibers which contain polyacrylonitrile or polyvinylidene cyanide. Their dyeings are in general very intense and have, for example, good fastnesses to light and to wetting processes, to chlorine and perspiration. They are resistant to a large degree to a change of the pH-value of the dyebath and can therefore be used both in a slightly acidic and in a strongly acidic bath. Wool is completely reserved by the dyestuffs under normal dyeing conditions.

Basic azo amino-phenylene dyestuffs

Compounds of the formula ##SPC1## Wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR.sub.1, --COR.sub.2, ##EQU1## --SO.sub.2 R.sub.2, ##EQU2## --CN, --NH.sub.2, --NO, --NO.sub.2 or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z.sub.1 is cyano, ##EQU3## --NH--OR.sub.10, ##EQU4## --OR.sub.12, --SR.sub.12 or --SO.sub.2 R.sub.12 and Z.sub.2 is chlorine, bromine, cyano, hydroxy, mercapto, --OR.sub.12, --SR.sub.12, --SO.sub.2 R.sub.12, ##EQU5## --NH--OR.sub.10 or ##EQU6## R.sub.1 is aliphatic; R.sub.2 is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R.sub.3 and R.sub.4 when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R.sub.3 and R.sub.4 when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R.sub.5 and R.sub.6 when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R.sub.5 and R.sub.6 when taken together with the nitrogen atom to which they are attached are heterocyclic; R.sub.7 is hydrogen, aliphatic or aromatic; R.sub.8 and R.sub.9 are aliphatic or aromatic, R.sub.10 is hydrogen, aliphatic or aralkyl, R.sub.11 is aliphatic and R.sub.12 is aliphatic, aromatic or aralkyl; R.sub.10 and R.sub.11 when taken together with the nitrogen atom to which they are attached are heterocyclic.

Certain 6-amino-4-hydrocarbyl-nicotinamides

2,6-Hydrazino-3-pyridine carboxyamides

Compounds of the formula Wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR.sub.1, --COR.sub.2, ##EQU1## --SO.sub.2 R.sub.2, ##EQU2## --CN, --NH.sub.2, --NO, --NO.sub.2 or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z.sub.1 is cyano, ##EQU3## --NH--OR.sub.10, ##EQU4## --OR.sub.12, --SR.sub.12 or --SO.sub.2 R.sub.12 and Z.sub.2 is chlorine, bromine, cyano, hydroxy, mercapto, --OR.sub.12, --SR.sub.12, ##EQU5## --NH--OR.sub.10 or ##EQU6## R.sub.1 is aliphatic; R.sub.2 is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R.sub.1 and R.sub.4 when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R.sub.3 and R.sub.4 when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R.sub.5 and R.sub.6 when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R.sub.5 and R.sub.6 when taken together with the nitrogen atom to which they are attached are heterocyclic; R.sub.7 is hydrogen, aliphatic or aromatic; R.sub.8 and R.sub.9 are aliphatic or aromatic, R.sub.10 is hydrogen, aliphatic or aralkyl, R.sub.11 is aliphatic and R.sub.12 is aliphatic, aromatic or aralkyl; R.sub.10 and R.sub.11 when taken together with the nitrogen atom to which they are attached are heterocyclic.

Certain 2-amino-nicotinonitrile derivatives

2-Hydrocarbyloxy-pyridine compounds

Basic azo dyestuffs, free from sulfo groups and having the formula Wherein Z is the radical of a tertiary amino group or of a quaternary ammonium group, Alk is alkylene of two to five carbon atoms, X is oxygen, Ar is phenylene unsubstituted or substituted by alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms and/or chlorine or bromine, and K as the radical of a coupling component is the radical of a tertiary amine of the benzene series, the radical of 2,6-diamino-3-cyano-4-methyl pyridine or a derivative thereof or the radical of the 2-hydroxynaphthalene series, which are suitable for the preparation of writing and stamping inks or pastes for ball-point pens as well as suitable in offset printing and for the dyeing, printing or mass dyeing of, for example, tannined cellulose fibers, silk, hair, leather, acetate silk, polyamide fibers or acid modified polyolefins, polyamide or polyester fibers and fibers containing polyacrylonitrile or polyvinylidene cyanide. The dyeings obtained on these fibers have, in general, a high color intensity and, in general, good fastness to light and to wet processing. The dyestuffs can be used in slightly acid and strongly acid baths and are stable at a temperature above 100.degree.C as used in high-temperature dyeing. Wool is completely reserved by the dyestuffs under normal dyeing conditions.

Growing community of inventors

Hofheim, Taunus, Germany

Erwin Fleckenstein